- Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis
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The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green
- Li, Han,Wenger, Oliver S.
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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; 0143; 0144
(2021/03/23)
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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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- BN-Substituted coronene diimide donor-acceptor-donor triads: photophysical, (spectro)-electrochemical studies and Lewis behavior
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Boron/nitrogen substituted polyaromatic hydrocarbons (PAHs) are unique materials, with similar molecular structures to their carbon/carbon analogs, but different electronic properties. We report how these may be tuned by substitution at the B and/or N ato
- Hissler, Muriel,Hoffmann, Jonas,Jacquemin, Denis,Staubitz, Anne
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p. 13926 - 13934
(2021/10/20)
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- The Concept of Photozymes: Short Peptides with Photoredox Catalytic Activity for Nucleophilic Additions to α-Phenyl Styrenes
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Conventional photoredox catalytic additions of alcohols to olefins require additives, like thiophenol, to promote back electron transfer. The concept of “photozymes” assumes that forward and backward electron transfer steps in a photoredox catalytic cycle
- Sack, Daniel,Wagenknecht, Hans-Achim
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supporting information
p. 6400 - 6407
(2021/11/18)
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- Organic anion sensitized photoconductive interface material as well as preparation method and application thereof
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The invention discloses an organic anion sensitized photoconductive interface material as well as a preparation method and an application thereof. The organic anion sensitized photoconductive interface material is obtained by compounding a conjugated fused ring imide small molecular compound capable of forming organic anions and an alkaline ionizable compound, the organic anion sensitized photoconductive interface material is used as a cathode interface layer of an organic solar cell, the performance of the organic solar cell can be greatly improved, a solution processing technology is adoptedin the preparation method of the organic anion sensitized photoconductive interface material, the preparation process is simple, and the manufacturing cost is low.
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Paragraph 0060-0063
(2021/01/29)
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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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- Fluorescent molecule, preparation method thereof, application thereof and fluorescence detection reagent (by machine translation)
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The invention discloses a fluorescent molecule, a preparation method thereof, an application thereof and a fluorescence detection reagent. A fluorescent molecule, which is a compound having the structure represented (1) by the following formula: wherein the compound is (1) as follows. In-flight vehicle R1 Alkyl group or substituted aromatic group and R group thereof2 A substituted aromatic group containing a-N&S * FF1D;N-N&S * FF1D;CH-group. -Né N-N&S * FF1D; N-N&S * FF1D; CH-group can specifically interact with hypochlorous acid, so that it can have naked eye recognition capability on hypochlorous acid, and simultaneously, the hypochlorite ion can be accurately, sensitively, specifically and efficiently detected. (by machine translation)
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Paragraph 0132; 0136-0137
(2019/12/02)
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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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- A novel perylene compound and use thereof
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The present invention relates to a novel dye compound and uses thereof. More particularly, the present invention provides a novel fluorescence-inhibited perylene dye compound which can be used as a color filter of a display element, a dye composition containing the same, and various uses such as a color filter. The dye composition of the present invention comprises: a perylene compound; a solvent; and a binder resin and a polymerizable compound.COPYRIGHT KIPO 2018
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Paragraph 0024; 0045; 0047-0050
(2018/07/28)
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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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- 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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p. 293 - 300
(2016/05/19)
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- PERYLENE BISIMIDE BASED COMPOUNDS AND DYES COMPRISING THE SAME
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Provided in the present invention are a novel perylene bisimide-based compound and a dye including the same. A novel dye is provided. And a color filter including the dye is provided. Provided in an embodiment of the present invention is a perylene bisimide-based compound represented by following chemical formula 1. [Chemical formula 1] The dye including the perylene bisimide-based compound according to the present invention has excellent fastness like light resistance and heat resistance.
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Paragraph 0127-0132
(2016/12/01)
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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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supporting information
p. 1792 - 1795
(2016/03/01)
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- Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter
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Six novel red perylene dyes were synthesized by modifying the bay- and terminal-positions of perylene main body to improve the optical performances of liquid crystal display (LCD) color filters. The absorption properties, solubility in industrial solvents and thermal stabilities of the dyes were examined to evaluate the dyes for dye-based LCD color filter. Mill bases and spin-coated color filters were formulated and fabricated using the synthesized dyes. Transmittance, dye aggregation and thermal stabilities of the prepared color filters were investigated using a color spectrophotometer. Geometric structures of the synthesized dyes were optimized by using Gaussian program. Five of the synthesized dyes showed acceptable optical properties as colorants for LCD color filters. Also, the synthesized dyes and prepared color filters exhibited suitable thermal stability for the application. Furthermore, the prepared color filters exhibited superior transmittances than pigment-based color filters at 650 nm. Their physical properties were closely related with chemical structures investigated by geometry optimization.
- Kim, Jeong Yun,Choi, Jun,Namgoong, Jin Woong,Kim, Se Hun,Sakong, Chun,Yuk, Sim Bum,Choi, Sang-A.,Lee, Woosung,Kim, Jae Pil
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p. 203 - 212
(2016/02/26)
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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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p. 6655 - 6662
(2014/08/05)
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- Synthesis, characterization and optoelectronic properties of a new perylene diimide-benzimidazole type solar light harvesting dye
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A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N′-bis(2,6-diisopropylphenyl)- 1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7- phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer.
- Din?alp, Haluk,?imen, Oguzhan,Ameri, Tayebeh,Brabec, Christoph J.,I?li, Siddik
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p. 197 - 206
(2014/04/17)
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- Competition between singlet fission and charge separation in solution-processed blend films of 6,13-bis(triisopropylsilylethynyl)pentacene with sterically-encumbered perylene-3,4:9,10-bis(dicarboximide)s
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The photophysics and morphology of thin films of N,N-bis(2,6- diisopropylphenyl)perylene-3,4:9,10-bis(dicarboximide) (1) and the 1,7-diphenyl (2) and 1,7-bis(3,5-di-tert-butylphenyl) (3) derivatives blended with 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-Pn) were studied for their potential use as photoactive layers in organic photovoltaic (OPV) devices. Increasing the steric bulk of the 1,7-substituents of the perylene-3,4:9,10- bis(dicarboximide) (PDI) impedes aggregation in the solid state. Film characterization data using both atomic force microscopy and X-ray diffraction showed that decreasing the PDI aggregation by increasing the steric bulk in the order 1 1*TIPS-Pn + TIPS-Pn → 2 3*TIPS-Pn) and charge transfer from 1*TIPS-Pn to PDIs 1-3. As the blend films become more homogeneous across the series TIPS-Pn:PDI 1 → 2 → 3, charge separation becomes competitive with singlet fission. Ultrafast charge separation forms the geminate radical ion pair state 1(TIPS-Pn +?-PDI-?) that undergoes radical pair intersystem crossing to form 3(TIPS-Pn+?-PDI -?), which then undergoes charge recombination to yield either 3*PDI or 3*TIPS-Pn. Energy transfer from 3*PDI to TIPS-Pn also yields 3*TIPS-Pn. These results show that multiple pathways produce the 3*TIPS-Pn state, so that OPV design strategies based on this system must utilize this triplet state for charge separation.
- Ramanan, Charusheela,Smeigh, Amanda L.,Anthony, John E.,Marks, Tobin J.,Wasielewski, Michael R.
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p. 386 - 397
(2012/03/07)
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- Facile synthesis and characterization of novel coronene chromophores and their application to LCD color filters
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New coronene derivatives, diphenylcoronene tetracarboxdiimide and monophenylbenzoperylene tetracarboxdiimide, were synthesized from N,N'-bis(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxdiimide via a one-step reaction. The suggested synthetic route is the simplest and most economical among the methods to extend the aromatic systems along the short molecular axis of perylene. The synthesized molecules exhibited superior stability and color strength as yellow chromophores. They were characterized by significant hypsochromic shifts of the absorption compared to perylene tetracarboxdiimide and high fluorescence quantum yields.
- Choi, Jun,Lee, Woosung,Sakong, Chun,Yuk, Sim Bum,Park, Jong S.,Kim, Jae Pil
-
-
- Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes
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Three near-infrared (NIR) absorbing unsymmetrical perylene diimide D-A-D type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO2 solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3-thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO2 nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO2 surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced.
- Dinalp, Haluk,Akar, Zuhal,Zafer, Ceylan,Li, Sddk
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p. 182 - 191
(2012/01/13)
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- Synthesis and characterization of some perylene dyes for dye-based LCD color filters
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Eight red perylene dyes were synthesized to improve the optical performance of LCD color filters. Among them, dyes with bulky functional substituents at the bay and terminal positions were highly soluble in cyclohexanone, the industrial solvent currently used in the pigment dispersion method. The spectral properties and thermal stability of the dye-based color filters with these dyes were examined by comparing them with pigment-based ones. The prepared color filters exhibited superior spectral properties due to the smaller particle size of the dyes, which led to less light scattering. However, their thermal stability varied with the dye structures, and only the dyes mono-substituted at the bay position had sufficient thermal stability.
- Choi, Jun,Sakong, Chun,Choi, Jae-Hong,Yoon, Chun,Kim, Jae Pil
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experimental part
p. 82 - 88
(2011/12/01)
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- Synthesis and optical properties of triphenylene-based dendritic donor perylene diimide acceptor systems
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A donor-acceptor charge transfer system based on two discotic mesogens has been synthesized. The donor is either a triphenylene (POG0) or a triphenylene-based conjugated dendron (POG1), while the acceptor is a perylene diimide (PDI) core. The donors are covalently linked to the bay positions of the PDI core through an ether linkage. In chloroform, due to the short donor-acceptor distance and the matching frontier orbital levels, photoinduced charge transfer from either the donor excitation or the acceptor excitation are both thermodynamically and kinetically favored, resulting in efficient quenching of both donor and acceptor fluorescence. In a less polar solvent, hexane, while charge transfer is still the dominant mechanism for decay of the excited electronic state of POG1, photoinduced charge transfer is no longer energetically favorable for POG0 when the acceptor PDI core is excited, making the PDI core of POG0 weakly fluorescent in chloroform but strongly so in hexane. In solid film, POG0 is highly aggregated through both PDI-PDI and triphenylene-triphenylene homotopic stacking. POG1, on the other hand, aggregates through triphenylene dendrons with limited PDI-PDI core stacking, presumably due to the steric hindrance caused by bulky triphenylene moieties which block the access to the PDI core. The efficient photoinduced charge transfer, coupled with the homotopic stacking that forms separated electron-transporting PDI-stacked columns and hole transporting triphenylene-stacked columns, suggests that the reported donor-acceptor systems based on dual-discotic mesogens are potentially new efficient photovoltaic materials.
- Bagui, Mahuya,Dutta, Tanmoy,Chakraborty, Sanjiban,Melinger, Joseph S.,Zhong, Haizhen,Keightley, Andrew,Peng, Zhonghua
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scheme or table
p. 1579 - 1592
(2011/05/06)
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- One-pot facile synthesis of pyridyl annelated perylene bisimides
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(Figure presented) Two regiospecifically pyridyl annelated perylene bisimides have been prepared in one pot by the combination of the Suzuki cross-coupling reaction and subsequent light-promoted cyclization In high yields.
- Jiang, Wei,Li, Yan,Yue, Wan,Zhen, Yonggang,Qu, Jianqiang,Wang, Zhaohui
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supporting information; experimental part
p. 228 - 231
(2010/03/30)
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- Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions
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Novel, symmetric and unsymmetric perylene diimide dyes with pyrene or indole units in the bay positions of the perylene ring were synthesized and characterized using FT-IR, 1H and 13C NMR, MS, UV-Vis spectra and cyclic voltammetry. The λmax in different solvents were in the range 526-585?nm and emission wavelengths of the dyes exhibited positive solvatochromism with increasing solvent polarity. Long wavelength emissions >750?nm of dyes with pyrene units displayed charge-separated state of perylene-pyrene system. Dyes with pyrene or indole units showed greater photostability in toluene than dyes which did not contain these bulky substituents. Incorporating electron-donating indole substituents lowered the band gap energies and, therefore, the HOMO energy levels were increased. The energy density and shape of the molecular orbitals were calculated theoretically.
- Din?alp, Haluk,Kizilok, ?evki,I?li, Siddik
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experimental part
p. 32 - 41
(2010/11/18)
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- PERYLENE TETRACARBOXIMIDE DERIVATIVES FOR PHOTOVOLTAIC DEVICES
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The compounds of the present invention are represented by the following formula (I): wherein M is represented by the following formula: with R1, R2, R3, R4, R5, R6, R7, R8, R10, R11, X1, X2, X3, L, a, b, c, d, e, x, y, and z defined herein.
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Page/Page column 11-12
(2010/04/03)
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- Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units: Facile synthesis and photophysical properties
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Two synthetic routes for the benzannulation in the "bay"-region of rylenebis(dicarboximide)s leading to new π-system-expanded chromophores are described. The first route follows a two-step approach: Suzuki coupling of bromo-substituted perylenebis(dicarbo
- Avlasevich, Yuri,Mueller, Sibylle,Erk, Peter,Muellen, Klaus
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p. 6555 - 6561
(2008/03/15)
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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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p. 4323 - 4331
(2007/10/03)
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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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p. 4443 - 4447
(2007/10/03)
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- Towards highly fluorescent and water-soluble perylene dyes
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A systematic approach towards highly fluorescent, water-soluble perylene-3,4:9,10-tetracarboxylic acid diimide chromophores is presented. Water solubility was introduced first through the attachment of four hydrophilic substituents onto the bay region of
- Kohl, Christopher,Weil, Tanja,Qu, Jianqiang,Muellen, Klaus
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p. 5297 - 5310
(2007/10/03)
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- Assembly and characterization of novel hydrogen-bond-induced nanoscale rods
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A class of bis-urea compounds with perylene bisimide was synthesized and characterized successfully. 1H NMR and fluorescence spectra confirmed that strong hydrogen-bonding interactions between neighboring urea groups were formed. Interestingly, the photocurrent measurement showed that the self-assembled films of bis-urea compounds could produce steady and rapid anodic photocurrent responses. The TEM images indicated that well-defined nanoscale rods with uniform diameter distribution could be fabricated by self-assembly of hydrogen-bonding interactions and π-π stacking interactions of perylene rings.
- Liu, Yang,Li, Yongjun,Jiang, Li,Gan, Haiyang,Liu, Huibiao,Li, Yuliang,Zhuang, Junpeng,Lu, Fushen,Zhu, Daoben
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p. 9049 - 9054
(2007/10/03)
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