- Tubular Perylene Bisimide Macrocycles for the Recognition of Geometrical Isomers of Azobenzenes
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Perylene bisimide-based materials are good candidates for photosensitive applications. Herein, we report synthesis, characterization, and complexation studies of perylene bisimide macrocycles obtained through bayside coupling. The isomeric macrocycles incorporated with interesting optical properties and tubular-shaped cavities are able to recognize geometric isomers of azobenzenes and aromatic amines. Such selective recognition is useful toward developing potential sensors for interesting isomeric pairs in the future.
- Bhargava, Samarth,Türel, Tankut,Valiyaveettil, Suresh
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- High-mobility air-stable n-type semiconductors with processing versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides)
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Taking up the semiconducting baton: Organic field-effect transistors fabricated with a new class of extremely electron-deficient cyanated perylene diimides are air-stable and exhibit n-type mobilities as high as 0.64 cm 2V-1 s-1 (see scheme). Devices can be fabricated from vapor-deposited and solution-cast films as well as top- and bottom-contact electrode configurations. (Graph presented).
- Jones, Brooks A.,Ahrens, Michael J.,Yoon, Myung-Han,Facchetti, Antonio,Marks, Tobin J.,Wasielewski, Michael R.
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- Synthesis and characterization of perylene diimide based molecular multilayers using CuAAC: Towards panchromatic assemblies
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Three perylene diimides (PDI) were synthesized with propargyl groups at the diimide positions to enable the fabrication of molecular multilayer thin films via sequential copper(i) catalyzed azide-alkyne cycloaddition (CuAAC) coupling reactions in a layer-by-layer (LbL) fashion. The new PDIs with phenoxy (PhO-PDI), dodecylthiol (Thiol-PDI), and pyrrolidine (Pyrr-PDI) substituents in bay positions have optical absorption spectra that span a large portion of the visible region. Multilayer growth on 11-azidoundecylsiloxane coated silica glass and indium tin oxide (ITO) surfaces was demonstrated up to 10 bilayers of each PDI with 1,3,5-tris(azidomethyl)-benzene (N3Mest) via optical and infrared spectroscopy. Polarized UV-visible absorption measurements showed a strong dependence on the orientation of the film in the light path and was consistent with a preferential orientation of the PDI molecules in the film at 40-42° with respect to the substrate surface. Grazing-angle attenuated total reflectance (GATR) infrared spectra of the films show an increase in content of unreacted azides during multilayer growth from N3Mest as a result of the smaller molecular footprint as compared to the PDI components. Electrochemical scans of the multilayer films grown on ITO exhibited reversible two-electron reduction waves for the PDIs with linear increases in charge with bilayer growth. The electrochemically derived surface coverages of PDIs averaged 1.2-1.3 × 1014 molecules per cm2 for each layer added to the multilayer films. The flexibility of the CuAAC based LbL assembly methodology is highlighted by the assembly of a mixed multilayer film containing five layers of each PDI, resulting in a panchromatic film that is a summation of individual chromophores. This journal is the Partner Organisations 2014.
- Beauvilliers, Evan E.,Topka, Michael R.,Dinolfo, Peter H.
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- Photophysical and electrochemical properties of 1,7-diaryl-substituted perylene diimides
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Substituent effects on the photophysical and electrochemical properties of 1,7-diaryl-substituted perylene diimides (1,7-Ar2PDIs) have been carefully explored. Progressive red-shifts of the absorption and emission maxima were observed when the electron-donating ability of these substituents was increased. Linear Hammett correlations of 1/λmax versus σ+ were observed in both spectral analyses. The positive slopes of the Hammett plots suggested that the electronic transitions carry certain amounts of photoinduced intramolecular charge-transfer (PICT) character from the aryl substituents to the perylene diimide core which leads to the reduction of the electron density on the substituents. The substituent electronic effects originated mainly from the perturbation of the core PDI HOMO energy level by the substituents. This conclusion was supported by PM3 analyses and confirmed by cyclic voltammetry experiments. More interestingly, the Ph2NC 6H4-substituted PDI, 4i, showed an unusual dual-band absorption that spans from 450 to 750 nm. We tentatively assigned these two bands as the charge-transfer band and the PDI core absorption, respectively.
- Chao, Chun-Chieh,Leung, Man-Kit,Su, Yuhlong Oliver,Chiu, Kuo-Yuan,Lin, Tsung-Hsien,Shieh, Shwu-Ju,Lin, Shien-Chang
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- Highly uniform supramolecular nano-films derived from carbazole-containing perylene diimide: Via surface-supported self-assembly and their electrically bistable memory behavior
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For electrical memory applications, two perylenetetracarboxylic diimide (PDI) derivatives, N,N′-(6-carbazole hexyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-6Cz) and N,N′-(2-carbazole ethyl)-1,7-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxylic diimide (PDI-2Cz), were synthesized and their surface-supported self-assembly behaviors were investigated. PDI-2Cz tends to self-organize into regular rods, which are proved to be hexagonal lattices with single crystal nature, based on which memory device fabrication and electrically bistable behavior evaluation are technically infeasible. Whereas PDI-6Cz readily self-assembles into highly uniform nano-films with a considerably smooth surface, in which the X-ray diffraction study indicates strong π-π stacking between the aromatic skeletons. Further characterization indicates that sandwich memory devices using a PDI-6Cz nano-film as the active layer exhibit reprogrammable flash-type memory behavior with a switching-on voltage of ca. 0.8 V and an ON/OFF current ratio of 104. Besides, the devices exhibit excellent long-term operation stability, enduring up to 108 reading cycles without obvious current variation and an ultrafast switching response period of less than 20 ns. Photophysical and electrochemical measurements and DFT molecular simulations were conducted to determine the electronic transition occurring in the supramolecular self-assembled nano-film. Compared with organic storage materials based on polymers, the current memory device exhibits lower threshold voltage and more rapid response speed, which provides a new way for developing high-performance organic data storage materials.
- Khan, Qudrat Ullah,Tian, Guofeng,Bao, Lin,Qi, Shengli,Wu, Dezhen
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- Bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide)s and their radical cations: Synthesis, electrochemistry, and ENDOR spectroscopy
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1,6- and 1,7-bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide) were synthesized by reaction of n-octylamine with the corresponding dibromo compounds. These compounds display intense charge-transfer optical transitions in the visible spectrum (~550-750 nm) and fluoresce weakly (ΦF 0.06). Cyclic voltammetry reveals that each chromophore undergoes facile and reversible oxidation and reduction. Spectroelectrochemical studies show that the radical cations of these chromophores are stable and show no signs of deprotonation of the secondary amines. Electron paramagnetic resonance (EPR) and electron-nuclear double resonance (ENDOR) studies of the chemically generated radical cations of these chromophores corroborate the spectroelectrochemical data by showing that the radical cations persist for days at room temperature in methylene chloride solution. These experiments and complementary density functional theory (DFT) calculations provide a comprehensive picture of the molecular orbitals, spin density distributions, and geometries of the radical cations. The redox properties and stability of these alkylamino-functionalized perylene compounds make them a valuable addition to the family of robust perylene-based chromophores that can be used to develop new photoactive charge transport materials.
- Ahrens, Michael J.,Tauber, Michael J.,Wasielewski, Michael R.
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- Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors
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In developing G-quadruplex interactive telomerase inhibitors two main features have to be taken into account: the hydrophobic interactions with the G-quartet plane and the electrostatic interactions with the negatively charged phosphates of the four grooves. In this paper, we report the synthesis of four hydrosoluble coronene derivatives, which are characterized by a large hydrophobic aromatic core and four orthogonal hydrophilic side chains. We have studied their ability to induce both inter- and intramolecular G-quadruplex structures and found a significant selectivity of all the coronene derivatives for the intramolecular G-quadruplex. The efficiency in inhibiting human telomerase has been evaluated in a cell-free system and the experimental results correlate with the relative affinities of these compounds for the G-quadruplex monomeric structure, as derived by molecular modelling simulations. Thus, the coronene derivatives can be considered as a new class of telomerase inhibitors, although further investigations are surely necessary to fully exploit their features.
- Franceschin, Marco,Alvino, Antonello,Casagrande, Valentina,Mauriello, Clementina,Pascucci, Emanuela,Savino, Maria,Ortaggi, Giancarlo,Bianco, Armandodoriano
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- Supramolecular 3,4:9,10-perylenetetracarboxylic diimide triads containing moieties of sumanene polyphenol derivative: Synthesis and photochemical transformations
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A polyphenol derivative of the sumanene-containing triad with a central perylenetetracarboxylic diimide moiety was synthesized via several consecutive chemical transformations of N,N'-bis(3',5'-dimethoxybenzyl)-1,7-bis[4''-(N,N'-disumanenyl)aminophenyl]perylene-3,4:9,10-tetracarboxylic diimide. The phenolic hydroxyl groups of the resulting derivative were partly protected by introduction of two different protective groups, pentaspiran and tert-butyl butyrate ones. It was shown that this modified derivative can be used to obtain a promising positive-tone photoresists with high parameters for extreme ultraviolet nanolithography on exposure to light at 13.5 nm for the manufacture of 20 to 16 nanometer chips.
- Vainer, A. Ya.,Dymaev,Kovalenko,Belskii,Krichevskaya,Martova
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- Controllable Monobromination of Perylene Ring System: Synthesis of Bay-Functionalized Perylene Dyes
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Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access a diverse range of new perylene systems.
- Takahashi, Masaki,Asaba, Kyohei,Lua, Trinh Thi,Inuzuka, Toshiyasu,Uemura, Naohiro,Sakamoto, Masami,Sengoku, Tetsuya,Yoda, Hidemi
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- Single-strand and ladder-type polymeric acceptors based on regioisomerically-pure perylene diimides towards all-polymer solar cells
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Since dibromo perylene diimides (DBPDIs) contain two isomers that are difficult to separate, isomeric effect on properties and applications of PDI polymers has been rarely studied. Few ladder-type polymers have been used in organic solar cells. Herein, si
- Wang, Lei,Hu, Ming,Zhang, Youdi,Yuan, Zhongyi,Hu, Yu,Zhao, Xiaohong,Chen, Yiwang
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- Synthesis of regioisomerically pure 1,7-dibromoperylene-3,4,9,10- tetracarboxylic acid derivatives
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The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10- tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10- tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.
- Sengupta, Sanchita,Dubey, Rajeev K.,Hoek, Rob W. M.,Van Eeden, Sjoerd P. P.,Gunbas?, D. Deniz,Grozema, Ferdinand C.,Sudh?lter, Ernst J. R.,Jager, Wolter F.
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- Novel fluorescence-enhancing effect based on light-induced E/Z isomerization of perylene diimides with Schiff-base groups on bay-positions
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Three novel perylene Schiff-base derivatives 5a-5c were synthesized and characterized in yields of 80–85%. They exhibited reversible trans/cis isomerization after UV-light irradiation and heating. The fluorescence-enhancing effects were firstly observed for perylene trans-to-cis isomerization. The increasing steric hindrance based on the restricted intramolecular rotation of trans-to-cis isomerization was responsible for the fluorescence-enhancing effect. The larger substituent on Schiff-based groups leaded to stronger fluorescence intensity and high quantum yield.
- Zhu, Mingguang,Guo, Hongyu,Cai, Kaicong,Yang, Fafu,Wang, Zusheng
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- Synthesis and photoelectric properties of donor-acceptor-donor molecule containing perylene diimide
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In this paper, a novel perylene diimide derivative 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide (PDI-TPA) was synthesized and characterized by IR spectroscopy, 1H NMR and elemental analysis. Besides, solubility and photoelectric properties of 1,7-bis[N,N-bis(4- phenyl)aniline]perylene diimide were studied. Results show that 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits excellent solubility in common solvents. The absorption bands span a wide range of the visible spectra and optical band gap is 1.68 eV. In addition, 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits an ambipolar behaviour, the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level are -5.64 eV and -3.94 eV, respectively.
- Jiao, Chun Ming,Li, Bing Jun,Yi, Si Li,Xu, Qing
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- A FRET-based ultraviolet to near-infrared frequency converter
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The synthesis and photophysical characterization of a generation 1 dendrimer containing four coumarin 2 laser dyes at the periphery and a perylenebis(dicarboximide) derivative at the core are described. It was found that 99% of the UV light absorbed by the peripheral coumarin 2 donor chromophores is transferred through fluorescence resonance energy transfer (FRET) to the core acceptor. Emission from the core via FRET is observed in the near-infrared with a 6.2-fold amplification relative to direct excitation. Copyright
- Serin, Jason M.,Brousmiche, Darryl W.,Frechet, Jean M. J.
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- Two novel rhodamine-perylenediimide fluorescent probes: Synthesis, photophysical properties, and cell imaging
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In this study, two novel dual-switch fluorescent chemosensors based on rhodamine-peryleneiimide have been designed and synthesized. The dual-switching behaviors of the sensors were based on the structural transformations of rhodamine and an intramolecular photoinduced electron transfer (PET) process from rhodamine to perylenediimide. These probes exhibited excellent sensitivity to protons with enhanced fluorescence emission from 500 nm to 580 nm. The fluorescence changes of probes were reversible within a wide range of pH values from 2.0 to 11.0. Moreover, the sensors exhibited high selectivity, short response time, and long lifetime toward protons. The possible mechanism was investigated by the DFT calculation and 1H NMR. According to the experiment of confocal laser scanning microscopy, these probes could be used to detect the acidic pH variations in living cells.
- Cheng, Huan-Ren,Qian, Ying
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- Novel perylene columnar liquid crystal tuned by azo isomerization on bay-positions
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Two azo-perylene derivatives (PBI-AZO-1 and PBI-AZO-2) with two alkyl chains and six alkoxy chains were designed and synthesized in yield of 63% and 49%, respectively. PBI-AZO-1 showed no mesophase but PBI-AZO-2 exhibited ordered hexagonal columnar mesophase based on the favorable effects of multiple alkyl chains. PBI-AZO-1 and PBI-AZO-2 exhibited the cis and trans azo-isomerization under radiation of UV light and the fluorescence quantum yields enhanced remarkably from 0.61 and 0.64 to 0.78 and 0.88, respectively. The ordered hexagonal columnar mesophase of PBI-AZO-2 was destroyed by isomerization due to the influence of asymmetrical mixture of cis and trans isomers. The transformation of liquid crystal/non-liquid crystal of PBI-AZO-2 before and after cis/trans isomerization displayed good reversibility by storing the sample for 15 days at room temperature. This kind of liquid crystallic behavior tuned by azo isomerization was first observed for perylene liquid crystal.
- Lin, Jianrong,Ji, Xiaoyu,Guo, Hongyu,Yang, Fafu
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- 1,6-Disubstituted perylene bisimides: Concise synthesis and characterization as near-infrared fluorescent dyes
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Detailed studies on bromination and subsequent imidization of perylene bisanhydride were reported. 1,6,7,12-Tetrabromoperylene bisimide was obtained in an optimized high yield. In addition, 1,6-disubstituted regioisomer was separated for the first time in isomerically pure form, and the structure was confirmed by 1H NMR, MS, element analysis, and photophysical measurements. By using a mixture of regioisomers 1,6- and 1,7-dibromo-perylene bisimide, 1,6-dipiperidinylperylene bisimides (1,6-Piper-Pery) were synthesized, purified, and their fluorescence were measured with a peak at 760 nm. These compounds can be used as stable near-infrared absorbing and fluorescent dyes.
- Fan, Liqiang,Xu, Yanping,Tian, He
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- Unsymmetric Bistable [c2]Daisy Chain Rotaxanes which Combine Two Types of Electroactive Stoppers
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Mechanically interlocked molecules (MIMs) have emerged as intriguing building blocks for the construction of stimuli-responsive devices and materials. A particularly interesting and well-implemented subclass of MIMs is composed of symmetric bistable [c2]daisy chain rotaxanes. Topologically, they consist in the double thread of two symmetric macrocycles that are covalently linked to an axle bearing two switchable stations and a bulky stopper to avoid unthreading. Herein we report the synthesis and characterization of a series of unsymmetric bistable [c2]daisy chain rotaxanes that present two different electroactive units as stoppers (an electron donor triarylamine and an electron acceptor perylene bisimide unit). Using a combination of 1D and 2D NMR along with cyclic voltammetry, we demonstrate that the pH actuation of the mechanical bond can be used to modulate the electrochemical properties of the bistable [c2]daisy chain rotaxanes when switching between the contracted and extended forms.
- Wolf, Adrian,Cid, Juan-José,Moulin, Emilie,Niess, Frédéric,Du, Guangyan,Goujon, Antoine,Busseron, Eric,Ruff, Adrian,Ludwigs, Sabine,Giuseppone, Nicolas
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- Synthesis of regioisomerically pure piperidine substituted perylenebisimide NIR dyes: A comparative study of spectroscopic, electrochemical and crystalline properties
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New regioisomerically pure green and blue dyes i.e. 1,7 and 1,6 piperidine substituted perylenebisimides (1A, 1B, 2A, 2B) were synthesized. Photophysical properties were compared with unsubstituted and brominated perylenebisimide analogues (1, 1PBr2, 2, 2PBr2). Piperidine was substituted on the bay region after imidization of dibromoperylene-3,4,9,10-tetracaboxylic dianhydride which induces strong bathochromic shifts. Large bathochromic shifts lower the optical band gaps which is the key feature of NIR absorbing fluorescent dyes with improved photovoltaic efficiencies. All synthesized fluorophores were characterized by NMR and Mass spectrometry. Photophysical properties were evaluated by UV–Vis, fluorimetry, and cyclic voltammetry. Fluorescence quantum yields were estimated by adopting a gradient method. The well-defined sharp peaks in X-ray diffraction pattern confirmed the crystalline nature of 1A and 1B. In contrast 2A and 2B were found non-crystalline. Thermal analysis by TG-DSC further explored the stability and phase transitions in dyes. HOMO and LUMO molecular orbitals were depicted by using density functional theory (DFT) at B3LYP/6–31(d,p). Electrochemical behaviors probed by cyclic voltammogram revealed dominant reversible oxidation reactions for 1,7 regioisomers (1A, and 2A) while both reversible oxidations and reductions were observed in 1,6 isomers (1B and 2B). Other structural analogues 1, 1PBr2, 2, 2PBr2 displayed reversible reductions. Thus a regular trend of changes in optical and electrical properties was observed on bromine and piperidine substitution. The observed outstanding properties clearly justify that our compounds might be promising candidates for various future applications such as biosensors, biomarkers, semiconductors, charge transporters, and stable fluorescent dyes.
- Hussain, Ejaz,Zhou, Huipeng,Yang, Na,Shahzad, Sohail Anjum,Yu, Cong
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- Bay Functionalized Perylenediimide with Pyridine Positional Isomers: NIR Absorption and Selective Colorimetric/Fluorescent Sensing of Fe3+ and Al3+ Ions
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Bay functionalized perylene diimide substituted with pyridine isomers, (2-pyridine (2HMP-PDI), 3-pyridine (3-HMP-PDI) and 4-pyridine (4-HMP-PDI)) have been synthesized and explored for selective coloro/fluorimetric sensing of heavy transition metal ions.
- Kundu, Anu,Pitchaimani, Jayaraman,Madhu, Vedichi,Sakthivel, Pachagounder,Ganesamoorthy, Ramasamy,Anthony, Savarimuthu Philip
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- New hydrosoluble perylene and coronene derivatives
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Several lipophilic perylene and coronene derivatives, employed mainly as liquid crystalline dyes are known and their synthesis has been widely studied. We have applied an analogue strategy using hydrophilic substituents to obtain highly water soluble perylene diimides (4) and a new hydrosoluble coronene derivative (CORON, 6), whose molecular features appear particularly suitable for inducing G-quadruplex DNA structures and inhibiting human telomerase.
- Franceschin, Marco,Alvino, Antonello,Ortaggi, Giancarlo,Bianco, Armandodoriano
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- Novel perylene liquid crystals: Investigation of the influence of bay-substituents on mesomorphism and photophysical property
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A series of perylene liquid crystals with H, Br, phenyl and tert-butylphenyl on bay-positions were synthesized in yields of 50-70%. Their mesomorphic properties and photophysical properties were investigated. The perylene derivatives 6, 7 and 8 with Br, phenyl and tert-butylphenyl at bay-positions have the hexagonal columnar liquid crystalline phase and wider scopes of phase transfer temperatures in comparison with similar perylene liquid crystal 5 with no substituent on bay-position. Compounds 6, 7 and 8 showed stronger fluorescence intensities, larger Stokes shifts and higher quantum yields than that of compound 5. These results indicated that the suitable substituents on bay-positions of perylene liquid crystals were favorable for producing excellent mesomorphic properties and good fluorescence properties.
- Zhu, Mingguang,Guo, Hongyu,Yang, Fafu,Wang, Zusheng
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- 1,6- and 1,7-regioisomers of dicyano-substituted perylene bisimides: Synthesis, optical and electrochemical properties
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In this study, 1,6- ad 1,7-regioisomers of dicyano-substituted perylene bisimides (1,6-C and 1,7-C) were synthesized and successfully isolated from their regioisomeric mixture using conventional methods of separation, and subsequently characterized by 400
- Tsai, Hsing-Yang,Chang, Che-Wei,Lin, Chi-Wei,Chen, Kew-Yu
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- Bay functionalized perylenediimide as a deaggregation based intracellular fluorescent probe for perchlorate
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The aggregates of perylenediimide based chemosensor (PDI 1) undergo de-aggregation induced fluorescence quenching selectively with ClO4-ions both in the solution and in the solid phase and can detect ClO4-ions in drinking water and fireworks. PDI 1 is permeable to C6 glioma cells, and ClO4-can be detected using confocal microscopy.
- Singh, Prabhpreet,Mittal, Lalit Singh,Vanita, Vanita,Kumar, Rahul,Bhargava, Gaurav,Walia, Amandeep,Kumar, Subodh
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- Water-soluble and highly emissive near-infrared nano-probes by co-assembly of ionic amphiphiles: Towards application in cell imaging
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Water-soluble near-infrared (NIR) fluorescent dyes are extremely valuable in cell imaging. We here designed and synthesized an amphiphilic fluorescent dye (denoted by PBI-TPE-11), a bolaamphiphile bearing conjugated tetraphenylethylene and perylene bisimide in the middle and two aliphatic pyridinium groups at both ends. PBI-TPE-11 self-assembled into flake-like nanostructures in aqueous solution and showed very weak fluorescence emission from 600 to 830 nm, covering the NIR region. This result seems discrepant with that previously reported in the literature, where the conjugation of PBI and TPE was proven enhance aggregation induced emission. Very interestingly, both the morphology and the emission intensity were altered by the addition of sodium dodecyl benzene sulfonate (SDBS). Co-assembly of PBI-TPE-11 and SDBS formed nanowires, observed by using an atomic force microscope. Moreover, the emission of the co-assemblies was much stronger than that of the assemblies of neat PBI-TPE-11. An exciting quantum yield (QY) of 15% was obtained for the co-assemblies, while pure PBI-TPE-11 showed a QY of merely 0.2%. Finally, the co-assemblies were successfully applied in labeling HeLa cells, and high viability and high contrast fluorescence images were achieved.
- Xing, Yuzhi,Li, Dahua,Dong, Bin,Wang, Xiaocheng,Wu, Chengfeng,Ding, Lan,Zhou, Shixin,Fan, Jian,Song, Bo
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- Synthesis and characterization of a new perylene bisimide (PBI) derivative and its application as electron acceptor for bulk heterojunction polymer solar cells
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A symmetrical perylene bisimide derivative (PBI) with 2-(4-nitrophenyl) acrylonitrile groups at the 1,7 bay positions of perylene and solubilizing cyclohexyl units was synthesized and characterized. The absorption spectrum of PBI was broad with the most prominent peak at 655 nm and optical band gap of 1.72 eV. The electrochemical investigation indicates that PBI has a LUMO energy level of -3.9 eV which is similar to that of PCBM or PC70BM. Bulk heterojunction solar cell fabricated using a blend of poly(3-hexylthiophene) (P3HT) and PBI (1:1 w/w) as active layer cast from THF exhibited power conversion efficiency (PCE) at 1.56%. However, the device with P3HT:PBI blend deposited from mixed solvent (DIO/THF) improved the PCE to 2.78% which further increased to 3.17% on using the thermal annealed active layer. The improvement in the PCE is attributed to the enhanced crystallinity of the blend (particularly P3HT) and increase in hole mobility leading to balanced charge transport.
- Sharma,Roy,Mikroyannidis,Justin Thomas
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- 1,7,9,10-Tetrasubstituted PMIs Accessible through Decarboxylative Bromination: Synthesis, Characterization, Photophysical Studies, and Hydrogen Evolution Catalysis
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In this work, we present a new synthetic strategy for fourfold-substituted perylene monoimides via tetrabrominated perylene monoanhydrides. X-ray diffraction analysis unveiled the intramolecular stacking orientation between the substituents and semicircular packing behavior. We observed the remarkable influence of the substituent on the longevity and nature of the excited state upon visible light excitation. In the presence of poly(dehydroalanine)-graft-poly(ethylene glycol) graft copolymers as solubilizing template, the chromophores are capable of sensitizing [Mo3S13]2? clusters in aqueous solution for stable visible light driven hydrogen evolution over three days.
- Costabel, Daniel,Skabeev, Artem,Nabiyan, Afshin,Luo, Yusen,Max, Johannes B.,Rajagopal, Ashwene,Kowalczyk, Daniel,Dietzek, Benjamin,W?chtler, Maria,G?rls, Helmar,Ziegenbalg, Dirk,Zagranyarski, Yulian,Streb, Carsten,Schacher, Felix H.,Peneva, Kalina
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- Synthesis of high-soluble and non-fluorescent perylene derivatives and their effect on the contrast ratio of LCD color filters
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We designed and synthesized perylene-based dyes for dye-based LCD color filters that highly soluble in organic industrial solvents, exhibit very weak fluorescence, and can be easily synthesized due to their simple molecular structures. The synthesized dyes were designed containing methoxy groups in the terminal-, bay-, or both positions for developing fluorescence quenched dyes. And, dyes with strong fluorescence and similar molecular structures to the fluorescence quenched dyes were also synthesized to clearly compare and analyze the effect of fluorescence on the optical properties. Finally, we fabricated dye-based color filters using the synthesized dyes and analyzed the optical performances of the color filters. The methoxy group in the bay-substituents has an enormous effect on the fluorescence quenching without the conspicuous influences on molecular behavior or dye aggregation. And, the fluorescence quenched dyes have remarkable effects in minimizing the increment of minimum brightness and prohibiting the contrast ratio decrease.
- Kim, Jeong Yun,Hwang, Tae Gyu,Kim, Se Hun,Namgoong, Jin Woong,Kim, Ji Eon,Sakong, Chun,Choi, Jun,Lee, Woosung,Kim, Jae Pil
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- Regioisomers of perylenediimide: Synthesis, photophysical, and electrochemical properties
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A series of conjugation extended donor-acceptor 1,6- and 1,7-regiomers of perylenediimide were synthesized, separated, and characterized. The photophysical, electrochemical, and thermal properties of these compounds were investigated and compared. The absorption spectra of 1,6-substituted PDI showed blue shift as compared to its 1,7-substituted PDI. At the same time, the emission spectrum showed no significant differences among the regiomers. Both 1,6- and 1,7-regiomers were thermally stable up to 450 ?°C and showed different melting and crystallization transitions. The electrochemical studies did not show significant differences in oxidation and redox potentials owing to similar HOMO/LUMO gap of 1,6- and 1,7-regiomers, which is also supported by theoretical calculations. Comparison of properties of a series of 1,6- or 1,7-substituted PDIs showed significant differences. Such regiomerically pure compounds can offer certain advantages in applications, which are currently being investigated. ? 2012 American Chemical Society.
- Keerthi, Ashok,Valiyaveettil, Suresh
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- Cell membrane permeable fluorescent perylene bisimide derivatives for cell lysosome imaging
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We have developed acid activated fluorescent probes based on amphiphilic perylene bisimide with morpholine groups on the bay (Lyso-APBI). Incorporating one morpholine group, Lyso-APBI-1 showed an acid activated fluorescence increase of 70-fold upon pH values lowering from 8.0 to 4.0. Lyso-APBI-2, with two morpholine groups on the bay of PBI, had a red-shifted emission and a 190-fold fluorescence enhancement within same pH variation range. These Lyso-APBI probes have excellent membrane permeability, low cytotoxicity, and can rapidly accumulate and specifically activate in cell lysosomes. The double morpholine moieties make Lyso-APBI probes have higher acid activation ratio and better cell lysosome specificity. Moreover, long-time cell imaging proved the relatively high photostability of Lyso-APBI probes in a harsh physiological environment.
- Zhang, Shuchen,Duan, Wenfeng,Xi, Yanan,Yang, Tao,Gao, Baoxiang
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- Spin-carrying naphthalenediimide and perylenediimide derivatives
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A couple of naphthalenediimide 4 and 5 and series of perylenediimide derivatives 6-9 carrying TEMPO radical were prepared and their redox, FET, and magnetic properties were investigated. The radical compounds 4 and 6-9 were found to show antiferromagnetic interactions obeying the Curie-Weiss model, while the naphthalenediimide derivative 5 exhibited a singlet-triplet magnetic behavior and it could be well understood by the short oxygen-to-oxygen distance between the spin centers observed in its crystal structure. Owing presumably to their appropriate reduction potentials and structural motifs, exhibitions of n-type FET properties were disclosed in these radical compounds with mobilities of the order from 10-5 to 10-8cm2 V-1 s-1 and apparent increase of mobilities was observed in the radical compounds 5 and 7 by the surface treatment with HMDS.
- Nakatsuji, Shin'ichi,Aoki, Kazunori,Akutsu, Hiroki,Yamada, Jun-Ichi,Kojima, Takahiro,Nishida, Jun-Ichi,Yamashita, Yoshiro
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- Synthesis and photovoltaic properties of novel alternating phenylenevinylene or fluorenevinylene copolymers containing perylene bisimide
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Two novel alternating phenylenevinylene copolymers P6 and P12 as well as one fluorenevinylene copolymer F connected at the 1,7 bay positions with perylene bisimide were synthesized by Heck coupling. They were characterized by GPC, FT-IR, 1H NMR, TGA, TMA, UV-vis, cyclic voltammetry and photoluminescence (PL) emission spectra. The copolymers were soluble in common organic solvents and thermally stable up to ~300 °C. Their glass transition temperatures were 48-60 °C. The long wavelength absorption maximum was located at 510-542 nm with optical band gaps of ~2.0 eV. The PL emission maximum of P6 and P12 was red-shifted relative to F. The photovoltaic performance of P6, P12 and F was also investigated.
- Mikroyannidis, John A.,Cheung, Kai Yin,Fung, Man Kin,Djuri?i?, Aleksandra B.
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- Low band gap thiophene-perylene diimide systems with tunable charge transport properties
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Perylenediimide-pentathiophene systems with varied architecture of thiophene units were synthesized. The photophysical, electrochemical, and charge transport behavior of the synthesized compounds were studied. Both molecules showed a low band gap of ~1.4 eV. Surprisingly, the molecule with pentathiophene attached via β-position to the PDI unit upon annealing showed a predominant hole mobility of 1 × 10-4 cm2 V-1 s-1 whereas the compound with branched pentathiophene attached via β-position showed an electron mobility of 9.8 × 10 -7 cm2 V-1 s-1. This suggests that charge transport properties can be tuned by simply varying the architecture of pentathiophene units.
- Balaji, Ganapathy,Kale, Tejaswini S.,Keerthi, Ashok,Della Pelle, Andrea M.,Thayumanavan,Valiyaveettil, Suresh
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- Retention of perylene diimide optical properties in solid-state materials through tethering to nanodiamonds
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The synthesis of nanodiamond-perylene diimide composites is reported. Suitably hydroxyl-functionalised perylene diimides (PDIs) are reacted with carboxylic acid functionalised nanodiamonds (NDs) through ester formation. The ND-PDI nanocomposite materials were characterised using a variety of different techniques confirming retention of the ND cores and interestingly the dye properties of the PDIs. In particular, fluorescence measurements suggest that PDIs tethered to NDs retain the characteristics of solution-phase PDIs rather than the optical properties associated with solid-state PDIs which are typically modified due to aggregation. Our relatively simple approach provides a mechanism for maintaining the solution-phase properties of PDIs in solid-state materials.
- Almuhana, Asia R. Y.,Champness, Neil R.,Griffin, Sarah L.,Langer, Philipp,Lodge, Rhys W.,Rance, Graham A.
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- Coronene-Containing N-Heteroarenes: 13 Rings in a Row
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We describe the modular synthesis of three novel large N-heteroarenes, containing 9, 11, and 13 annulated rings. This modular system features fused azaacene units to a coronene nucleus. We evaluate the optical and electronic properties and the solid-state packing of the targets. The electronic properties of the 13-ring N-heteroarene allow the fabrication of a proof-of-concept thin-film transistor. Electron mobilities up to 8 × 10-4 cm/(V s) were obtained for polycrystalline films.
- Endres, Alexander H.,Schaffroth, Manuel,Paulus, Fabian,Reiss, Hilmar,Wadepohl, Hubert,Rominger, Frank,Kr?mer, Roland,Bunz, Uwe H. F.
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- Highly thermal-stable perylene-bisimide small molecules as efficient electron-transport materials for perovskite solar cells
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Perylene-bisimide (PDI)-based small molecules (PDI-Ph, PDI-PhCN, PDI-PhCN-2Br and PDI-PhCN-4Br) were synthesized via imidization of perylene bisanhydride and core-bromided perylene bisanhydride. The physical, optical and electronic properties of these molecules were characterized by thermogravimetric analysis (TGA), UV-Vis, X-ray diffraction (XRD), cyclic voltammetry and space charge-limited current (SCLC). PDI-Ph, PDI-PhCN and PDI-PhCN-2Br show excellent thermal stability with decomposition temperatures above 400 °C (610 °C for PDI-PhCN) and high crystallinity with strong π-π stacking. The three molecules also exhibit high electron mobility with average values of 0.169 cm2 V-1 s-1 for PDI-Ph, 0.212 cm2 V-1 s-1 for PDI-PhCN and 0.119 cm2 V-1 s-1 for PDI-PhCN-2Br. Utilizing these molecules as the single electron-transporting layer (ETL), inverted perovskite solar cells with a configuration of ITO/NiOx/MAPbClxI3-x/ETL/Ag were fabricated. A power conversion efficiency of 14.6% was achieved from the device using PDI-PhCN as ETL. Furthermore, when BCP was used as the hole-blocking layer, the identical structured perovskite device achieved a high efficiency of 18.8% for the PDI-PhCN/BCP combination, which was better than the standard cell (17.4%) using C60/BCP as ETL. The superior performance of PDI-PhCN compared to PDI-Ph, PDI-PhCN-2Br and PDI-PhCN-4Br comes from its higher electron mobility and better matched energy levels with that of the absorber MAPbClxI3-x. Our results demonstrate that PDI-based small molecules are very promising electron-transporting materials for highly efficient, low-cost perovskite solar cells. This journal is
- Gong, Yuancai,He, Zhaoxia,Huang, Wei,Jiang, Jingjing,Lu, Di,Xia, Ruidong,Xin, Hao,Yan, Weibo,Yang, Wensheng
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- Synthesis, mesomorphic and photophysical properties of novel triads and pentads of perylene liquid crystals with cholesterol units at the bay-position
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Series of triads and pentads of perylene derivatives with two cholesterol units at the bay-position or four cholesterol units on both bay-position and imide position were designed and synthesized in yields of 55-65%. The influence of the different number and position of cholesterol substituents on mesomorphic properties and photophysical properties was studied. The results suggested that, in comparison with similar perylene derivatives with alkyl units at the imide position, the perylene liquid crystals with alkyl units at the bay-positions not only maintained excellent mesomorphic properties but also enhanced the fluorescence greatly. More cholesterol units resulted in a lower mesophase temperature, wider phase transfer temperature range, and higher fluorescence. A long spacer between perylene and cholesterol units led to more excellent mesomorphic properties and higher fluorescence.
- Zhu, Mingguang,Guo, Hongyu,Yang, Fafu,Wang, Zusheng
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- Evaluation of Perylenediimide Derivatives for Potential Therapeutic Benefits on Cancer Chemotherapy
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Perylene derivatives, known to have potential therapeutic benefits on particular cancer types as photosensitizers, may also function as small-molecule inhibitors with promising therapeutic value for diverse diseases. This recently recognized biological activity was attributed to their capacity to modulate the function of various enzymes as biological targets in vitro. Although the inhibitory activity on glutathione transferase and Src tyrosine kinase is important in determining the anticancer potential of compounds for target-specific drug design and development, to date, there are no successful inhibitors of this kind. Moreover, there are only a few studies about the effects of perylene derivatives on glutathione transferase and various kinases. In this study, four novel perylene compounds, N,N′-disubstituted perylenediimides and their 1,7-dibromo derivatives, were synthesized and evaluated for their biological activities. Here, among the compounds analyzed, one of them was identified with strong glutathione transferase inhibition and two with dual activity for both glutathione transferase and c-src inhibition. These results revealed that perylene derivatives may be employed as potential chemosensitizers to prevent chemotherapy-dependent drug resistance and identified as prospective anticancer agents with dual activity on both glutathione transferase and c-src enzymes.
- Keskin, Taner,Isgor, Belgin S.,Isgor, Yasemin G.,Yukruk, Funda
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- Regioisomerically pure 1,7-dibromo-substituted perylene bisimide dyes: Efficient synthesis, separation, and characterization
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1,7-Dibromo-substituted perylene bisimides have been obtained in yields of at least 60% in regioisomerically pure form by treating the commonly used dibromoperylene-3,4,9,10-tetracarboxylic dianhydride with 2-(diethylamino)ethylamine or 2-(dimethylamino)ethylamine and then separating the 1,7-isomer from the regioisomeric mixtures by conventional column chromatography and without recrystallization. The individual regioisomers were fully characterized by 1H NMR spectroscopy and HRMS. The signals of the protons located in the aromatic region and neighboring the imide nitrogen atom were utilized to confirm the chemical structures of the isomers. The 1,7-dibromo isomer obtained with 2-(dimethylamino)ethylamine in such a convenient and efficient way was further used to prepare 1,7-disubstituted perylene bisimide derivatives by saponification, amidation, and then bay-position substitution reactions. These compounds exhibited a significant redshift and broadening of their absorption and emission in optical spectroscopy analysis.
- Ma, Jiajun,Yin, Leicheng,Zou, Gang,Zhang, Qijin
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- Bis(porphyrin)-3,4:9,10-perylenetetracarboxydiimide triads as new building blocks for the synthesis of aromatic polyethers
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It was shown that aromatic polyethers (APs) containing in the main chain bis(porphyrin) perylenediimide triads as new building blocks can be obtained. Thermal properties of the prepared APs showing high glass transition temperature were studied. Negative photoresists based on the final unsaturated polymer and anthrylsulfonium salt were designed.
- Vainer,Dyumaev,Kovalenko,Dragunskaya,Bel'Skii,Khait
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- Asymmetric perylene bisimide dyes with strong solvatofluorism
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Two asymmetric perylene bisimide dyes, 1-cyano-7-piperidinylperylene bisimide (1) and 1-bromo-7-piperidinylperylene bisimide (2), were synthesized and fully characterized. These molecules undergo an excited-state intramolecular electron transfer reaction, resulting in a unique charge transfer emission, of which the peak wavelength exhibits strong solvatochromism. They show both larger ground-state and excited-state dipole moments than those of the symmetric perylene bisimide 3; the dipole moments of these compounds have been estimated using density functional theory calculations and the Lippert-Mataga equation. Furthermore, these dyes (1-3) display good thermal stability as well as good optical stability and reversible redox properties. Their spectroscopic properties in various conditions and complementary time-dependent density functional theory calculations are reported.
- Luo, Ming-Hui,Chen, Kew-Yu
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- Proton triggered circularly polarized luminescence in orthogonal- and co-assemblies of chiral gelators with achiral perylene bisimide
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The orthogonal- or co-assembly of achiral perylene bisimide (PBI) with chiral gelators can be regulated by solvents. While the coassembly leads to the formation of chiroptical nanofibers through chirality transfer, the orthogonal assemblies could not. Moreover, protonation on the coassembled nanofibers could light up the circularly polarized luminescence (CPL).
- Han, Dongxue,Han, Jianlei,Huo, Shengwei,Qu, Zuoming,Jiao, Tifeng,Liu, Minghua,Duan, Pengfei
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- Pyrene fused perylene diimides: Synthesis, characterization and applications in organic field-effect transistors and optical limiting with high performance
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Three pyrene fused PDI derivatives have been obtained, in which totally different properties were observed when adopting different fusing types. For bilaterally benzannulated PDIs, through spin-coating, bottom-contact OFET devices exhibited a p-type mobility up to 1.13 cm2 V-1 s-1, with an on/off ratio of 108 in air. This journal is
- Zhan, Xuejun,Zhang, Ji,Tang, Sheng,Lin, Yuxuan,Zhao, Min,Yang, Jie,Zhang, Hao-Li,Peng, Qian,Yu, Gui,Li, Zhen
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- Fine-Tuning the Electronic Properties of Azo Chromophore-Incorporated Perylene Bisimide Dyads
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Perylene bisimide (PBI) and azo-compounds are fascinating molecules with interesting optical properties. Here, we combine the two chromophores to prepare nonconjugated and conjugated stable azo-PBI dyes. The detailed structural characterization, comparison of properties, and solid-state self-assembly of the compounds are discussed. The incorporation of azo groups at the bay side of PBI led to significant changes in optical properties as compared to the model PBIs (M1 and M2). All new azo-PBIs showed photoinduced isomerization, which caused disaggregation and enhancement in fluorescence. The amine-incorporated azo-PBIs (3 and 6) reduced chloroauric acid into gold nanoparticles. The current study offers a simple synthetic strategy and comparison of the properties of conjugated and nonconjugated azo-PBIs, which could be useful in photoelectronic devices.
- Türel, Tankut,Valiyaveettil, Suresh
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- Bay region borylation of perylene bisimides
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Novel bispinacolborane-N,N′-bis(octyl)-3,4,9,10- perylenetetracarboxylic acid bisimide (PBI) was synthesized in high yield. The title compound is a key intermediate in the preparation of PBI aryl derivatives through Suzuki cross-coupling by using a large variety of easily accessible aryl halides. The benign effect of a nonpolar solvent, mild base, and high reaction temperature on the borylation reaction was studied, and the reaction conditions were optimized accordingly. To demonstrate the potential and flexibility of the proposed building block, two corresponding bisarylperylene bisimides were prepared in high yields. For the first time, an efficient and straightforward method was developed for thesynthesis of bis-pinacolborane-N,N′-bis(octyl) -3,4,9,10-perylene tetracarboxylic bisimide derivatives by using a commercially available Pd catalyst. Two Suzuki cross-coupling reactions of novel bispinacolborane perylene derivative are also reported.
- Dey, Somnath,Efimov, Alexander,Lemmetyinen, Helge
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- Triphenylene–perylene–triphenylene triads with bay-substituents: synthesis, mesomorphism, and electron transfer properties
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Three novel triphenylene–perylene–triphenylene triads 5, 6, and 7 with short amido spacer and bay-substituents (H, Br, and tert-butylphenyl) were synthesized in yields of 40–70%. Their structural and conformational characterization had been achieved by FT-IR, NMR, and HR-MS. The studies of liquid crystalline behaviors suggested that triads 5, 6, and 7 possessed hexagonal columnar mesophase. The bay-substituents were favorable for decreasing the phase transitions temperature and enlarging the ranges of phase transfer temperatures. Their absorption spectra were similar to the absorption bands of analogues of triphenylene and perylene. Their fluorescence spectra exhibited strong Dexter electron transfer between triphenylene moiety and perylene moiety, resulting in drastic fluorescence quenching. The larger π–π conjugated system of perylene core enhanced the electron transfer property.
- Guo, Hongyu,Zhu, Mingguang,Wang, Zusheng,Yang, Fafu
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- Stimuli-responsive circularly polarized luminescence from an achiral perylenyl dyad
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Stimuli-responsive circularly polarized luminescence (CPL) was successfully achieved through fine-tuning the conformation of a perylenyl dyad by using external stimuli. Monomer CPL was clearly detected from an inherent achiral monochromophore system in a simple perylene-carbazole dyad, and concentration-dependent CPL was observed from 'good solvent', giving an excimer-like CPL emission with a peak maximum at 643 nm. Moreover, the CPL bands depended on the aggregated state, which was identical to the emission changes in the THF-H2O system. It is noteworthy that the perylene-carbazole dyad emitted efficient CPL in thin films even without annealing processes. The specific perylenyl-carbazole structure plays a crucial role in CPL in response to the external environment. This novel molecular design strategy opens up a new perspective for the future development of smart CPL-active organic dyads.
- Li, Junfeng,Yang, Chenglong,Peng, Xuelei,Qi, Qi,Li, Yonghua,Lai, Wen-Yong,Huang, Wei
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- Synthesis and spectroscopic properties of highly water-soluble perylene derivatives
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Most known perylene diimides are lipophilic, with few exceptions of hydrophilic derivatives. Even in the latter case, the compounds have limited water solubility and show a strong tendency to self-aggregation. In this paper we present the synthesis of four new perylene derivatives with three and four basic side chains, obtained by functionalizing the bay-area of perylene. These molecules show great solubility in aqueous media as hydrochlorides and their tendency to self-aggregate is remarkably reduced with respect to the previously synthesized two-chained perylene diimides. Their different spectroscopic properties in various solvents and conditions are reported and discussed.
- Alvino, Antonello,Franceschin, Marco,Cefaro, Chiara,Borioni, Silvia,Ortaggi, Giancarlo,Bianco, Armandodoriano
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- Donor-acceptor copolymers with 1,7-regioisomers of: N, N ′-dialkylperylene-3,4,9,10-tetracarboxydiimide as materials for photonics
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Donor-acceptor (D-A) copolymers containing N,N′-dialkylperylene-3,4,9,10-tetracarboxydiimide electron-acceptor units with dodecyl (DDPDI) or 2-ethylhexyl (EHPDI) substituents and three different electron-donor units (9,9-dioctylfluorene, 9-(2-ethylhexyl)carbazole or 9-(heptadecan-9-yl)carbazole) were synthesized by Suzuki coupling and were then characterized. Their thermal, photophysical, electrochemical and spectroelectrochemical properties were studied. The effects of the alkyl side chain combination on the properties were evaluated and are discussed. Despite large differences in the absorption spectra of the individual DDPDI and EHPDI units or monomers in solutions and thin films, the absorption spectra of the copolymers in solutions and thin films exhibited similar shapes. More pronounced side chain effects were observed in the photoluminescent (PL) behaviour than in the absorption behaviour. Different alkyl side chains on the D-A copolymers similarly affected the visible absorption band contributions in the solutions and thin films, but the exhibited effects were different for the PL spectra and efficiency. The copolymers exhibited reversible reduction and irreversible oxidation. The ionization potential and bandgap values were influenced by the donor unit and by the perylene-3,4,9,10-tetracarboxydiimide (PDI) side chain nature. Spectroelectrochemical changes are reported, and potential sensing applications are outlined.
- Cimrová, Věra,Vyprachticky, Drahomír,Pokorná, Veronika,Babi?ová, Petra
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- The effect of fluorescence of perylene red dyes on the contrast ratio of LCD color filters
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Dye-based and pigment-dye hybrid color filters are recommended to overcome the drawbacks such as light scattering of traditional pigment-based color filters. However, dyes used as colorants for LCD color filters may exhibit strong fluorescence. Fluorescence lowers the contrast ratio of color filters by increasing brightness in the full-black state and affects optical performance of displays. In this study, the correlation between dye fluorescence and the optical properties of color filters was investigated. Six perylene-based dyes were synthesized, and dye-based and pigment-dye hybrid color filters were prepared with each dye. The fluorescence properties of the synthesized dyes in solution and the prepared color filters were evaluated. The maximum brightness and the contrast ratio of the color filters were measured, from which the minimum brightness of the color filters was calculated. All dye-based and pigment-dye hybrid color filters showed greater minimum brightness than pigment-based one due to emission in the visible region.
- Kim, Jeong Yun,Sakong, Chun,Choi, Sang-A,Jang, Hyeyoun,Kim, Se Hun,Chang, Kil Seong,Han, Myoung Sic,Lee, Jeong Su,Kim, Jae Pil
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- Preparation method and application of nucleon targeted photo-thermal reagent based on perylene bisimide
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The invention discloses a preparation method and application of a perylene bisimide-based nucleolus targeting photo-thermal reagent. To the method, bromine substituted perylene imide is firstly obtained through reaction of liquid bromine and perylene anhydride. The substitution group is then introduced into the imide position and the bay position by the reaction of the amino group and the acid anhydride and nucleophilic substitution reaction of the amino group and the bromine, namely, the perylene bisimide-based nucleolus targeting photo-thermal agent is obtained. The synthetic photothermal reagent is a compound capable of specifically and strongly binding with a nucleic acid, and the binding force enables the photothermal reagent to be rapidly taken (within three minutes) and enriched to DNA by cells. RNA, The targeted effect on nucleolus kernels is superior to that of commercialized dye nuclei green. The synthetic photothermal reagent is good in water solubility, good in light, heat and chemical stability, high in light absorption in the near infrared region, good in photothermal conversion efficiency, excellent in photo-thermal killing effect on tumor cells and capable of realizing photothermal therapy of cancer cells.
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Paragraph 0031-0033
(2021/09/08)
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- Modulating optical and electrochemical properties of perylene dyes by twisting aromatic π-system structures
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Three highly fluorescent perylene bisimide dyes were synthesized, where aromatic π-system structures are twisted to different degree by steric hindrance of two or four substitution groups at bay position. Light-emitting colours of these dye solutions can be modulated from green, yellow to red, and their fluorescence quantum yields increase up to approximate 100% with increasing the π-system twisting, which can be considered for new class of wavelength-tunable dye lasers. π-Twisted dyes are more sensitive to microenvironment changes. Thus, they are better fluorescence probe and sensory materials than planar dyes. Electrochemical cyclic voltammetry measurements revealed that these dyes are suitable for n-type optoelectrical devices and materials. These dye solids display near infra-red emission at 600–850 nm. Owing to strong π-π stacking interaction, planar dye solid loses its outstanding optical properties compared to its solution. In contrast, π-twisted dye solids retain their excellent optical properties including narrow emission bands and relatively high fluorescence quantum yields due to the suppression of π-π stacking interaction. Exceptional fluorescence polarization phenomena were observed for these π-twisted dye solids. These optical results revealed that π-twisted perylene bisimide dyes are more excellent optical materials than planar dyes.
- Wang, Ying,Zhang, Qi,Gong, Junbo,Zhang, Xin
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- Perylene diimide derivative-based near-infrared two-region aggregation-induced light-emitting molecule and preparation method and application thereof
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The invention provides a perylene diimide derivative-based near-infrared two-region aggregation-induced light-emitting molecule and a preparation method and application thereof. Firstly, perylene diimide is used as a receptor structural unit to perform coupling reaction with a large-sized donor unit to obtain a near-infrared two-region aggregation-induced light-emitting molecule based on a perylene diimide structure. The molecule is connected with a donor structure with a larger size on both sides of the perylene diimide core with high conjugated rigidity, so that the strong π - pi stacking effect of the perylene diimide core can be effectively inhibited, so that the molecule has aggregation-induced emission (AIE) property. The near-infrared two-region aggregation-induced light-emitting molecule and the amphiphilic lipid molecules DSPE-PEG5000 are self-assembled. The obtained water-soluble nanoparticles have good fluorescence intensity in the near-infrared two-region, imaging application in the near-infrared two-region can be realized, and the conjugated molecules also have good photothermal conversion efficiency and can be used for photothermal therapy of tumors.
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Paragraph 0048-0055
(2021/09/29)
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- Tuning the aggregation behaviour of BN-coronene diimides with imide substituents and their performance in devices (OLEDs and OFETs)
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Compared to perylene diimides (PDIs), coronene diimides (CDIs), which can be viewed as a lateral core extension, show undesired effects for optoelectronic devices such as the decrease of the absorption and a hypsochromic shift. Here, we demonstrate that, if the core is extended with two BN units as opposed to two CC units, the opposite is true: large bathochromic shifts can be achieved, together with higher molar extinction coefficients and beneficial luminescence properties,e.g.small Stokes shifts and high quantum yields (Φlum> 94%). These effects can be explained by the influence of the BN-unit on the frontier molecular orbitals of theBNCDIs. Different substitution motifs at the imide position, cyclohexyl and 2,6-diisopropylphenyl, although they had no influence on the optical properties on a single molecule level, influenced the aggregation substantially so that the optical properties in the solid state and the performance in organic devices (OLEDs and OFETs) differed considerably. In combination with host matrices, devices with EQEs of up to 1.5% and white light emission (0.317; 0.346) were obtained. The developed synthetic route starting from a regioisomeric pure 1,7-substituted PDI leads toBNCDIs in good yields, which makes this class of compounds very promising.
- Geffroy, Bernard,Hissler, Muriel,Hoffmann, Jonas,Jaques, Emmanuel,Staubitz, Anne
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p. 14720 - 14729
(2021/11/09)
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- Low dielectric dye type black matrix for color filter on array
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The present invention relates to a low dielectric dye type black matrix for a color filter array structure. More specifically, the present invention relates to a tetrabenzoate (tetrabenzocorrolazine) dye having high color intensity, a broad absorption range, low dielectric and high durability, a photosensitive resin composition including the dye, a black matrix including the dye, and a color filter including the black matrix.
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Paragraph 0049; 0140-0142
(2021/03/23)
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- NARROW ABSORPTION POLYMER NANOPARTICLES AND RELATED METHODS
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Polymers, monomers, narrow-band absorbing polymers, narrow-band absorbing monomers, absorbing units, polymer dots, and related methods are provided. Bright, luminescent polymer nanoparticles with narrow-band absorptions are provided. Methods for synthesizing absorbing monomers, methods for synthesizing the polymers, preparation methods for forming the polymer nanoparticles, and applications for using the polymer nanoparticles are also provided.
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Page/Page column 184
(2020/04/25)
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- Swallow tail bay-substituted novel perylene bisimides: Synthesis, characterization, photophysical and electrochemical properties and DFT studies
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Novel, one bay-substituted perylene bisanhydride (6) and two bay-substituted perylene bisimides (7, 10) have been successfully synthesized with a large and swallow tail type, 2-decyl-1-tetradecanoyl substituents at the bay area (1 and 7 positions). The non-bay-substituted perylene bisimides with the same N-substituents were prepared as model compounds (3, 9) for comparison. Absorption and fluorescence, electrochemical, spectroelectrochemical, morphological properties of the compounds were investigated, and then, density functional theory (DFT) simulations were conducted. The compounds 6, 7 and 10 have shown J-aggregated featureless, very broad absorbance through the UV–vis-NIR region with a strong fluorescence quenching attributed to efficient intramolecular electron transfer from electron donor 2-decyl-1-tetradecanoyl substituent to PDI acceptor and scaffolds allow π–π intermolecular interactions, induced molecular aggregation. The absolute positions of LUMO and HOMO values for 3, 9, 6, 7 and 10 in solutions were ?3.91/?6.09 eV, ?3.93/?6.08 eV, ?4.02/?5.90 eV, ?4.02/?5.91 eV and ?4.02/?5.97 eV, respectively. The onset reduction potential of compounds 6, 7 and 10 are lower than those of compounds 3 and 9. Similarly, the onset oxidation potential values of the compounds 6, 7 and 10 are smaller than those of the non-bay-substituted perylene dyes 3 and 9. The synthesized compounds (3 with 7; 9 with 10) can be exploited as an off-on fluorescence probes for photonic applications.
- Al-Khateeb, Basma,Dinleyici, Meltem,Abourajab, Arwa,K?k, Cansu,Bodapati, Jagadeesh B.,Uzun, Duygu,Koyuncu, Sermet,Icil, Huriye
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- Engineering Intrinsic Flexibility in Polycrystalline Molecular Semiconductor Films by Grain Boundary Plasticization
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Mechanically flexible films of the highly crystalline core-cyanated perylenediimide (PDIF-CN2) molecular semiconductor are achieved via a novel grain boundary plasticization strategy in which a specially designed polymeric binder (PB) is used to connect crystallites at the grain boundaries. The new PB has a naphthalenediimide-dithiophene ?-conjugated backbone end-functionalized with PDI units. In contrast to conventional polymer-small molecule blends where distinct phase separation occurs, this blend film with plasticized grain boundaries exhibits a morphology typical of homogeneous PDIF-CN2 films which is preserved upon bending at radii as small as 2 mm. Thin-film transistors fabricated with PB/PDIF-CN2 blends exhibit substantial electron mobilities even after repeated bending. This design represents a new approach to realizing flexible and textured semiconducting ?-electron films with good mechanical and charge transport properties.
- Chen, Jianhua,Chen, Zhihua,Facchetti, Antonio,Guo, Xugang,Huang, Wei,Marks, Tobin J.,Wang, Binghao,Wang, Gang,Yu, Junsheng,Zhao, Dan
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supporting information
(2020/03/10)
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- PHOTOPERIODIC CONTROL OF PHYTOCHROME WITH MATERIALS
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Disclosed herein are articles and devices, such as photo-selective films, which may be used to influence the growth of photosynthetic organisms. These article and devices may comprise one or more compounds of Formula (I) and/or Formula (II), along with one or more optional auxiliary dyes. Methods of controlling the growth of plants and for the manufacture of said articles and devices are also disclosed herein.
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Paragraph 0317-0319
(2020/08/28)
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- The synthesis and characterisation of the perylene acid dye inks for digital textile printing
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Five perylene acid dyes were synthesized to manufacture water-based inks for the high-speed ink jet printing process, including digital textile printing. All the synthesized perylene dyes exhibited superior stability and optical properties compared to a commercially used azo dye. Their water solubility was efficiently enhanced by introducing bulky and hydrophilic substituents to ensure excellent long-term stability when formulated as water-based inks. The water-based inks with these perylene dyes showed outstanding print clarity with the colours different from the basic colour composition of the existing digital textile printing inks. They also exhibited good ejection performance and helped conduct well-controlled pattern printing when used in a commercial ink jet printing machine.
- Choi, Sol,Cho, Kwan Hyun,Namgoong, Jin Woong,Kim, Jeong Yun,Yoo, Eui Sang,Lee, Woosung,Jung, Jae Woong,Choi, Jun
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p. 381 - 392
(2019/01/03)
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- Synthesis of bay-linked perylene dimers with enhanced solubility for high optical density black matrix material
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Perylene diimides (PDIs) have been used in various industries, especially in devices such as organic light-emitting diodes, organic semiconductors, and thin-layer organic photovoltaics, because of their excellent optical and electrical properties and outstanding thermal stability. In addition, PDIs are suitable for black matrix and black bank materials, which require wide and strong absorption of visible light, for use in display panels. Research has been conducted to apply solution-processed PDI on the black matrix and black bank film fabrication. However, due to the low solubility of PDI, industrially required optical properties have not been achieved. In this study, diphenyl-linked PDI dimers were synthesized and evaluated on their optical properties and thermal stability for solution-processed black matrix. The solubility of the synthesized dimers was improved compared to that of monomers as intermolecular interaction reduced by two PDI cores in a molecule that is rotated at a specific angle. Five kinds of dimeric and monomeric PDIs were synthesized with bay substituents of different electron donating power. The absorption range of the dyes was red-shifted as the electron donating power of the substituents increased, and the fluorescence of the dyes was quenched by intramolecular charge transfer (ICT). In a solution state, dimers showed enhanced absorbance and thermal stability and enlarged absorption range as compared to the monomers. Hybrid-type black matrices using dimeric PDIs and carbon black showed high thermal stability, flat surface condition, and low dielectric constant. Additionally, the optical density of the black matrices, which was not satisfactory in the previous study, was greatly improved (up to 2.755) because of the increased dye content due to highly soluble dimeric PDIs.
- Yuk, Sim Bum,Lee, Jae Moon,Namgoong, Jin Woong,Sakong, Chun,Hwang, Tae Gyu,Kim, Se Hun,Lee, Woosung,Kim, Jae Pil
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- HIGH TRANSMISSIONAL YELLOW DYE FOR LCD AND SYNTHETIC METHOD THEREOF
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The present invention relates to a highly transmissive yellow dye for LCD and a preparation method thereof, and more specifically, to a highly transmissive yellow dye for LCD, a dye dispersion body including the dye, a coloring composition including the dye dispersion body, a color filter including the coloring composition, and a method of preparing the dye. The method of preparing a highly transmissive yellow dye for LCD according to one embodiment of the present invention includes a step of forming a first intermediate; a step of forming a second intermediate; and a step of forming a dye compound.
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Paragraph 0054-0057
(2020/03/23)
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- "COMPOUNDS AS POTENTIAL DYE MOLECULES"
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Disclosed herein are a series of compounds based on Formula (I). These compounds comprise perylene core which has been extended with optionally functionalised imidazoles at the 3,4;9,10 positions. The compounds of Formula (I) can be functionalised at two positions on the perylene core, such as the 1,6 or 1,7 positions. Also disclosed herein are compositions comprising said compounds, methods of forming said compounds and potential applications of said compounds, such as applying the compounds as a dye whose absorbance and fluorescence spectrum are red-shifted.
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Paragraph 0160; 0161
(2019/02/26)
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- Synthesis and characterization of fluorescent dyes and their applications for the enhancement of growth rate of Chlorella vulgaris
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Spectral conversion of solar radiation from green to red light can enhance the photosynthesis efficiency of microalgae. This can lead to significant increase in microalgal growth. Four perylene-based fluorescent dyes were synthesized to convert wavelengths of light from green (500–570 nm) to orange-red (580–650 nm). These dyes were applied in microalgal cultivation system using two methodologies: (1) light-converting layer, and (2) light-converting medium. The dyes were dissolved in either ethanol or water to form light-converting layers between microalgae culture and the light source. Under converted light in both set-ups, Chlorella vulgaris cultures showed maximum increase in lipid productivity by 13.00% and 17.15%, and biomass productivity by 31.65% and 37.66% compared to the control. Overall, the cultivation results confirmed beneficial effects of modified light on microalgae cultures both on their lipid and biomass productivities. Note that both growth parameters achieved higher performance in the light-converting medium thereby the effectiveness of the cultivation method was validated.
- Jang, Hyeyoun,Namgoong, Jin Woong,Sung, Min-Gyu,Chang, Yongkeun,Kim, Jae Pil
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p. 142 - 150
(2018/05/28)
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- Preparation method of fluorescent dye and water-soluble near-infrared fluorescent probe
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The invention provides a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent probe, and belongs to the technical field of chemical synthesis. The invention provides aperylene diimide derivative, wherein R1 is a conjugated group with aggregation-induced emission characteristics, and R2 is pyridinium salt with alkyl chains of different lengths, PEG (polyethylene glycol) with different chain lengths or tri-PEG benzene. The derivative is prepared from 3,4,9,10-perylenetetracarboxylic dianhydride as a raw material through the following chemical reactions: (1) 3,4,9,10-perylenetetracarboxylic dianhydride and bromine are subjected to a reaction in a molar ratio of 1 to (1 to 10) to obtain 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride; (2) 1,7-dibromo-3,4,9,10-perylenetetracarboxylic dianhydride and trimethyl tin-tetraphenyl ethylene are subjected to a reaction under the catalysis of Pd(PPh3)4 to obtain a coupling product; and (3) the coupling product and an amine-terminated compound are subjected to a reaction, and the reaction product is bonded with hydrophilic pyridine bromide onium salt or PEG in an anhydride position to obtain the target product. The obtained water-soluble fluorescent material can be used for near-infrared cell imaging.
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Paragraph 0052; 0058; 0064; 0070; 0079
(2018/05/16)
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- The effect of imide substituents on the optical properties of perylene diimide derivatives
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As one of the most important organic semiconductors, perylene diimide derivatives (PDIs) have been widely applied in optoelectronics. Two kinds of soluble PDIs with different imide substituents have been synthesized and their optical properties have been investigated. The photoluminescence (PL) intensity of the PDI with amino phenyl imide substituents (NH2-PDI) is much lower than that of the PDI with octyl imide substituents (O-PDI). It can be found that the Stokes shift of O-PDI is positive, whereas, the Stokes shift of NH2-PDI is negative. The emission intensity of the 0–0 electron transition relative to that of the 1–0 electron transition (I0–0/I1–0) in the PL spectrum of O-PDI is decreased, but the value of I0–0/I1–0 in the PL spectra of NH2-PDI is increased as the dielectric constant of the solvent increases. The large overlap between the absorption and PL spectra plays an important role to result in the low PL intensity of NH2-PDI. The PL decay data show that a non-radiative process, photoinduced electron transfer, also contributes to the low PL intensity of NH2-PDI. The results can help researchers to understand the effect of the imide substituents on the optical properties of PDIs.
- Kong, Fan,Lin, Mengqi,Qiu, Teng
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p. 1209 - 1216
(2018/09/12)
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- Preparation method and application of near-infrared dye functionalized intelligent super-molecule vesicle
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The invention discloses a preparation method and an application of a near-infrared dye functionalized intelligent super-molecule vesicle. According to the preparation method, water solubility column [5] aromatic hydrocarbon (WP5) serves as a main body, a biquaternary ammonium salt functionalized near-infrared dye G based on perylene diimide serves as an objective body, the intelligent super-molecule vesicle is constructed by the aid of acting force of the main body and the objective body between the water solubility column [5] aromatic hydrocarbon and the near-infrared dye, and efficient loading of a drug (hydrophobic anticancer drug adriamycin) can be achieved in the self-assembly process. The near-infrared dye G has excellent near-infrared photo-thermal conversion performance and can serve as a photo-thermal treatment reagent of a tumor. The super-molecule drug load vesicle constructed by the aid of the acting force of the main body and the objective body between the WP5 and the near-infrared dye can stably exist in physiology environments and can rapidly and efficiently release a photo-thermal treatment reagent and a chemotherapy drug in tumor acidic micro-environments, collaborative treatment of photo-thermal treatment/chemotherapy is achieved, the super-molecule drug load vesicle is provided with a good drug delivery system, treatment effect of the tumor is greatly improved, and the super-molecule drug load vesicle has an excellent clinical application prospect.
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Paragraph 0046; 0047; 0048; 0049
(2018/10/11)
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- A study on the fluorescence property of the perylene derivatives with methoxy groups
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Perylene-based dyes with methoxy groups at various positions were synthesized to understand the effect of the methoxy groups on the fluorescence quenching. Additionally, perylene-based dyes with ethyl groups in place of the methoxy groups were also synthesized to serve as control. Absorption and fluorescence properties of the dyes were measured, and then, density functional theory (DFT) and time-dependent density functional theory (TD-DFT) simulations were conducted. The methoxy groups of terminal-substituents had a lesser effect on fluorescence quenching than the methoxy groups of bay-substituents. Moreover, only the methoxy groups at the para-position of the bay-substituents strongly affected on fluorescence quenching. These results showed that the fluorescence of the dyes are influenced by the electron donating effect of the methoxy groups when the methoxy groups are involved in the main conjugation systems of the dyes.
- Kim, Jeong Yun,Woo, Sung Wun,Namgoong, Jin Woong,Kim, Jae Pil
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p. 196 - 205
(2017/09/22)
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- A New π-conjugated 1,7-diphenoxy-perylene bisimide: Synthesis, characterization, photophysical and electrochemical properties
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A novel π-conjugated 1,7-diphenoxy-perylene bisimide (perylene diimides, PDIs) (4) was synthesized starting from 1,7(6)-diphenoxyperylene-3,4,9,10-tetracarboxylic bisanhydride (3). N,N’-bis(4-hydroxyphenyl)-perylene-3,4,9,10-tetracarboxy bisimide (1) was synthesized and characterized also for the comparison between a non-bay substituted symmetrical perylene diimide and the bay substituted symmetrical perylene diimide with the same substituents at the PDI imide positions. Positive and weak solvatochromic effect for the compounds 3 and 4 was apparently observed in polar media. The absolute positions of LUMO and HOMO values of 1 and 3 in solution were ?3.775 eV/?6.035 eV and ?3.971 eV/?6.041, respectively. The HOMO, LUMO and Eg values for the compound 4 were not calculated due to the non-resolved reduction peaks most probably due to aggregation.
- Pakseresht, Mayram,Bodapati, Jagadeesh B.,Icil, Huriye
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p. 270 - 277
(2018/05/22)
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- PIGMENTS FOR LIGHT SHIELD LAYER AND PHOTO-CURABLE RESIN COMPOSITION USING THE SAME
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The present invention provides a pigment for light-shielding layers, comprising a compound represented by chemical formula 1. In the chemical formula 1, R^1 and R^2 are each independently a cyano group, a hydroxy group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C3-C20 cycloalkynyl group, a substituted or unsubstituted C2-C20 heterocycloalkyl group, a substituted or unsubstituted C2-C20 heterocycloalkenyl group, a substituted or unsubstituted C2-C20 heterocycloalkynyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C6-C30 aryloxy group. The pigment for light-shielding layers according to the present invention has superior heat resistance and dispersibility compared to a conventional parylene black.COPYRIGHT KIPO 2017
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Paragraph 0057; 0058; 0059; 0060; 0061; 0062
(2017/07/23)
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- Perylene diimide organic third-order nonlinear optical material, and preparation and application of perylene diimide organic third-order nonlinear optical material
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The invention relates to a perylene diimide organic third-order nonlinear optical material. 3,4,9,10-perylenetetracarboxylic diimide serves as a core group; cyclohexane and benzanthrone or triphenylamine serve as substituent groups; cyclohexane is connected with an imide nitrogen atom of the core group; and benzanthrone or triphenylamine is connected with a bay of the core group to form a whole. A preparation method comprises the steps: (1) adding a perylene diimide derivative, a benzanthrone derivative or a triphenylamine derivative with the imide nitrogen atom connected with cyclohexane, and potassium carbonate into a solvent for dissolution, (2) after supplying nitrogen for 1-30 min, adding a tetrakispalladium catalyst, heating to 80-100 DEG C at a speed of 500-1200 r/min for reaction for 3-24h , (3) carrying out extraction, knockout and dryness for many times by using dichloromethane and distilled water, and (4) separating and purifying an obtained crude product. The perylene diimide organic third-order nonlinear optical material has a large nonlinear absorption coefficient and a two-photon absorption cross-section value and is applied to a third-order nonlinear optical material aspect.
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Paragraph 0036
(2017/08/23)
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- Langmuir-Blodgett films of perylene bisimide derivatives and fluorescent recognition of diamines
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Fast, sensitive and selective detection of diamines in the vapor phase is of pivotal importance for air and food quality monitoring. In this work, an electron-poor fluorophore, perylene bisimide (PBI), was modified with hydrophilic residues at its bay positions, resulting in an amphiphilic derivative, PEBBO. Photophysical studies revealed that the compound shows a strong aggregation tendency in various solvents, but the aggregates could be highly fluorescent provided suitable solvents are used. Accordingly, a fluorescent film was constructed via utilization of the well-known Langmuir-Blodgett technique. Sensing performance studies revealed that the film as prepared is sensitive and selective to the presence of diamines in air. Specifically, (1) the experimental detection limit is lower than 0.016 g m-3 and the linear range of the analysis extends from 0.33 g m-3 to 8.20 g m-3 when ethylenediamine was adopted as an example analyte; (2) the presence of other amines and solvents shows little effect upon detection; (3) the response time is less than 5 s. Considering the importance of diamine sensing, the convenience of fluorescence techniques and the superiorities of the film and method as developed, it is believed that the present work is of great importance for promoting technical progress in diamine sensing.
- Shang, Congdi,Wang, Li,An, Yanqin,Chen, Ping,Chang, Xingmao,Qi, Yanyu,Kang, Rui,Fang, Yu
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p. 23898 - 23904
(2017/09/22)
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- Ionic Self-Assembled Platform of Perylenediimide–Sodium Dodecylsulfate for Detection of Spermine in Clinical Samples
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The detection and quantification of spermine in clinical practice is important for early diagnosis of many diseases. Chromatographic and immunoassay-based methods are commonly used. However, a fluorescence-based assay could provide real-time detection. Herein, the synthesis and aggregation properties of a dicationic perylene probe (N1-dodecyl-N3-(4-phenyl)benzimidazolium-functionalized perylenediimide (DAB-PDI)) used to develop a fluorescent “turn-on” ensemble for the detection of spermine are discussed. The fluorescence of DAB-PDI (10 μm, Φ=0.55) is efficiently quenched by negatively charged sodium dodecylsulfate (SDS) through the formation of ionic self-assembled aggregates (charge ratio of negative (N) in SDS to positive (P) in DAB-PDI (N/P)=9). This negatively charged ionic self-assembly between DAB-PDI and SDS has been characterized by using photophysical, microscopic, dynamic light scattering, isothermal titration calorimetry, and HRMS techniques. The addition of spermine to this ensemble solution results in the breakdown of the DAB-PDI–SDS ensemble owing to strong binding of spermine with SDS and, as a result, the fluorescence of DAB-PDI is recovered. This ensemble exhibits high sensitivity and selectivity for spermine detection in water, urine, and blood serum. The lowest limit of detection is 27.5 nm, which is at least about 36 times lower than that required for early diagnosis of cancer (1 to 10 μm for urinary spermine).
- Singh, Prabhpreet,Mittal, Lalit Singh,Bhargava, Gaurav,Kumar, Subodh
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supporting information
p. 890 - 899
(2017/04/24)
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- ENERGY STORAGE MOLECULAR MATERIAL, CRYSTAL DIELECTRIC LAYER AND CAPACITOR
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The present disclosure provides an energy storage molecular material, crystal dielectric layer and capacitor which may solve a problem of the further increase of volumetric and mass density of reserved energy associated with some energy storage devices, and at the same time reduce cost of materials.
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Page/Page column 28
(2016/12/07)
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- [...] derivatives and their use
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The invention relates to an N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative and application thereof. The N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative refers to the compound shown as a formula II in the specification or salts thereof. The designed and synthesized N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative can be used for preparing perylene pigments such as C.I.pigment red 149. The perylene pigment prepared by the N,N'-dimethyl-3,4,9,10-perylenetetracarboxylic diimide derivative disclosed by the invention has large specific surface area and narrow particle size distribution.
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Paragraph 0055; 0056; 0057; 0058
(2016/11/21)
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- Self-assembled nanorods of bay functionalized perylenediimide: Cu2+ based 'turn-on' response for INH, complementary NOR/OR and TRANSFER logic functions and fluorosolvatochromism
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We designed and synthesized the mono bay functionalized perylenediimide (PDI) derivative PDI-DMEA which undergoes self-assembly to form a nanorod morphology. The diameter of these nanorods is in the range of 150-300 nm and the length extended up to the μm range. These nanorods on interaction with Cu2+ ions transformed into spherical aggregates having a diameter of 350-600 nm in accordance with DLS studies. In solution, PDI-DMEA shows a blue shift of the internal charge transfer (ICT) absorption band from 605 to 570 nm along with a hyperchromic effect at 570 nm, in the presence of 0.7 equivalents of Cu2+ ions. The addition of 2 equivalents of Cu2+ ions results in complete disappearance of the ICT band at 570 nm and appearance of a normal absorption band of PDI at 515 nm (a visual colour change from colourless to yellow). On the other hand PDI-DMEA shows a strong fluorescence 'turn-on' response at 537 and 573 nm on addition of higher equivalents of Cu2+ ions. Thus, PDI-DMEA represents several examples of molecular switches such as 'OFF-ON-OFF' and 'ON-OFF-ON' at 570/515 nm (Cu2+, absorbance), and 'OFF-ON' at 570 nm (Fe2+, absorbance) and 537 nm (Cu2+, fluorescence) and thus offers the possibility for developing NOR, OR, INH and TRANSFER logic and complimentary logic circuits. Moreover, PDI-DMEA and the PDI-DMEA-Cu2+ complex show fluorosolvatochromism which helps to develop a colour array for differentiating organic solvents. The detailed mechanism of interaction of Cu2+ and Fe2+ with PDI-DMEA, confocal laser scanning microscopic studies, dynamic light scattering, 1H NMR titration and reversibility are discussed.
- Singh, Prabhpreet,Kumar, Kapil,Bhargava, Gaurav,Kumar, Subodh
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p. 2488 - 2497
(2016/07/14)
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