- Star-shaped D-π-A molecules containing a 2,4,6-tri(thiophen-2-yl)-1,3,5- triazine unit: Synthesis and two-photon absorption properties
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A series of new star-shaped donor-π-acceptor (D-π-A) mole-cules containing the 2,4,6-tri(thiophen-2-yl)-1,3,5-triazine unit were synthesized and characterized. The 1,3,5-triazine group, as a strong electron-accepting center, is connected to three electron
- Zou, Li,Liu, Zijun,Yan, Xiaobing,Liu, Yan,Fu, Yang,Liu, Jun,Huang, Zhenli,Chen, Xingguo,Qin, Jingui
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Read Online
- Synthesis and characterization of electron donor-acceptor platinum(II) complexes composed of N, N -diphenylpyridineamine and triphenylamine ligands
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The synthesis and electronic properties of a series of platinum(II) complexes composed of electron-donor and electron-acceptor components as potential photovoltaic materials is reported. The complexes are composed of triphenylamines (TPA) and pyridine-derivatized TPAs as the electron-donating components, and alkynyl derivatives of 2,1,3-benzothiadiazole and cyclopentadithiophenone as the electron acceptors. The complexes containing the pyridine-derivatized ligands were prepared to examine the effect that direct coordination of a heteroatom-modified TPA may have on the electronic properties of donor-acceptor (D-A) complexes. Four complexes composed of meta- and para- pyridine-derivatized TPAs were prepared, and their electronic properties were compared with three structurally similar complexes composed of TPA, as well as with purely organic D-A compounds. Data collected from UV-vis and cyclic voltammetry show minor differences on the properties of the complexes containing the pyridine-derivatized ligands when compared to the TPA analogs, exhibiting similar highest occupied molecular orbital-lowest unoccupied molecular orbital bandgaps ranging from 2.156 to 2.705 eV for the pyridine-derivatized complexes (6a,b and 7a,b), 2.038-2.320 eV for the TPA complexes (8a,b and 9a), 2.301 eV for organic molecule 10a, and 1.997 eV for 10b. All compounds are stable, exhibiting no decomposition in the solid indefinitely, and only minor decomposition in solution. All compounds were characterized by 1H and 13C nuclear magnetic resonance, infrared spectroscopy, and electrospray mass spectrometry. All complexes were also characterized by 31P nuclear magnetic resonance and elemental analysis of CHN; determination of Ag content for 6a,b and 7a,b (carried through the synthetic steps) was determined by inductively coupled plasma optical emission spectrometry. The para-pyridine-derivatized complex of 2,1,3-benzothiadiazole (6a) was further characterized by X-ray crystallography as a AgNO3 clathrate. X-ray quality crystals were grown from a solution of hexanes/CH 2Cl2 and from diffusion of hexanes into a CH 2Cl2 solution of the complex, providing a solvent-free crystal and a solvate of CH2Cl2, respectively.
- Dai, Zhi,Metta-Magana, Alejandro J.,Nunez, Jose E.
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- Tuning photovoltaic performance of DOBT-based dyes via molecular design with ethynyl-linker and terminal electron-donating segment
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Two novel D-π-A-π-D-typed dioctyloxy-benzothiadiazole (DOBT)-based small molecules (SMs), TPAEDOBT and CZEDOBT, were designed and synthesized, consisting of ethynyl as π-linkage, besides, incorporating triphenylamine (TPA) and alkylated-carbazole (Cz) as
- Wang, Lihui,Yin, Lunxiang,Wang, Lijuan,Xie, Bao,Ji, Changyan,Li, Yanqin
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Read Online
- Rational Design and Facile Synthesis of Dual-State Emission Fluorophores: Expanding Functionality for the Sensitive Detection of Nitroaromatic Compounds
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Six novel benzimidazole-based D-π-A compounds 4 a–4 f were concisely synthesized by attaching different donor/acceptor units to the skeleton of 1,3-bis(1H-benzimidazol-2-yl)benzene on its 5-position through an ethynyl link. Due to the twisted conformation and effective conjugation structure, these dual-state emission (DSE) molecules show intense and multifarious photoluminescence, and their fluorescence quantum yields in solution and solid state can be up to 96.16 and 69.82 %, respectively. Especially, for excellent photostability, obvious solvatofluorochromic and extraordinary wide range of solvent compatibility, DSE molecule 4 a is a multifunctional fluorescent probe for the visual detection of nitroaromatic compounds (NACs) with the limit of detection as low as 10?7 M. The quenching mechanism has been proved as the results of photoinduced electron transfer and fluorescence resonance energy transfer processes. Importantly, probe 4 a can sensitively detect NACs not only in real water samples, but also on 4 a-coated strips and 4 a@PBAT thin films.
- Chen, Si-Hong,Luo, Shi-He,Xing, Long-Jiang,Jiang, Kai,Huo, Yan-Ping,Chen, Qi,Wang, Zhao-Yang
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- Broadband visible light-absorbing [70]fullerene-BODIPY-triphenylamine triad: Synthesis and application as heavy atom-free organic triplet photosensitizer for photooxidation
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A broadband visible light-absorbing [70]fullerene-BODIPY-triphenylamine triad (C70-B-T) has been synthesized and applied as a heavy atom-free organic triplet photosensitizer for photooxidation. By attaching two triphenylmethyl amine units (TPAs) to the -core of BODIPY via ethynyl linkers, the absorption range of the antenna is extended to 700 nm with a peak at 600 nm. Thus, the absorption spectrum of C70-B-T almost covers the entire UV-visible region (270-700 nm). The photophysical processes are investigated by means of steady-state and transient spectroscopies. Upon photoexcitation at 339 nm, an efficient energy transfer (ET) from TPA to BODIPY occurs both in C70-B-T and B-T, resulting in the appearance of the BODIPY emission at 664 nm. Direct or indirect (via ET) excitation of the BODIPY-part of C70-B-T is followed by photoinduced ET from the antenna to C70, thus the singlet excited state of C70 (1C70 *) is populated. Subsequently, the triplet excited state of C70 (3C70 *) is produced via the intrinsic intersystem crossing of C70. The photooxidation ability of C70-B-T was studied using 1,5-dihydroxy naphthalene (DHN) as a chemical sensor. The photooxidation efficiency of C70-B-T is higher than that of the individual components of C70-1 and B-T, and even higher than that of methylene blue (MB). The photooxidation rate constant of C70-B-T is 1.47 and 1.51 times as that of C70-1 and MB, respectively. The results indicate that the C70-antenna systems can be used as another structure motif for a heavy atom-free organic triplet photosensitizer.
- Chen, Hong,Dou, Li-Feng,Gong, Yu,Lu, Hong-Dian,Mao, Li-Hua,Wang, Xue-Fei,Wei, Chun-Xiang,Yang, Wei,Zhang, Jian-Hui,Zhu, San-E.
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- Metallated Graphynes as a New Class of Photofunctional 2D Organometallic Nanosheets
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Two-dimensional (2D) nanomaterials are attracting much attention due to their excellent electronic and optical properties. Here, we report the first experimental preparation of two free-standing mercurated graphyne nanosheets via the interface-assisted bottom-up method, which integrates both the advantages of metal center and graphyne. The continuous large-area nanosheets derived from the chemical growth show the layered molecular structural arrangement, controllable thickness and enhanced π-conjugation, which result in their stable and outstanding broadband nonlinear saturable absorption (SA) properties (at both 532 and 1064 nm). The passively Q-switched (PQS) performances of these two nanosheets as the saturable absorbers are comparable to or higher than those of the state-of-the-art 2D nanomaterials (such as graphene, black phosphorus, MoS2, γ-graphyne, etc.). Our results illustrate that the two metallated graphynes could act not only as a new class of 2D carbon-rich materials, but also as inexpensive and easily available optoelectronic materials for device fabrication.
- Huang, Bolong,Li, Jiahua,Sun, Jibin,Sun, Mingzi,Tang, Tianhong,Wang, Zhengping,Wong, Wai-Yeung,Xie, Zheng,Xu, Linli,Zhang, Hongyang,Zhang, Jianqi
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p. 11326 - 11334
(2021/04/09)
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- Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties
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For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.
- Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai
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p. 9692 - 9704
(2021/11/30)
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- Synthesis of alkynes under dry reaction conditions
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An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.
- Rao, Maddali L.N.,Shamim Islam, Sk
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supporting information
(2021/04/19)
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- Isoquinoline sulfonamide functional molecular materials with adjustable excited state, and preparation method and application thereof
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The invention belongs to the field of photoelectric materials, and particularly discloses isoquinoline sulfonamide functional molecular materials with an adjustable excited state, and a preparation method and application thereof. The invention also discloses the preparation method and the application method of the isoquinoline sulfonamide functional molecular materials with the adjustable excited state. According to the invention, substituent groups (diethylamino, diphenylamine and carbazole) functional molecule isoquinoline sulfonamide compounds with different electron donating capabilities and steric hindrance are synthesized. The configuration and energy of the excited state are regulated and controlled by means of a solvent effect, a steric effect and the like, so that the optical and electrical properties of molecules are regulated, and the multifunctional integrated organic molecular material has the advantages of adjustable and controllable excited state, single-molecule double-wave emission and realization of organic single-molecule white light emission. The materials can be applied to energy storage, safety anti-counterfeiting, screen display, environment monitoring and the like required by multifunctional materials.
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Paragraph 0057; 0078-0080
(2021/07/08)
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- Direct iodination of electron-deficient benzothiazoles: Rapid access to two-photon absorbing fluorophores with quadrupolar D-π-A-π-D architecture and tunable heteroaromatic core
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Direct iodination of benzothiazoles under strong oxidative/acidic conditions leads to a mixture of iodinated heteroarenes with 1-2 major components, which are easily separable and which structures depend on the I2 equivalents used. Among the unexpected bu
- Fakis, Mihalis,Georgiou, Dimitris,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Rakovsky, Erik
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p. 3460 - 3465
(2021/05/31)
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- Oxidative C-H Homocoupling of Push-Pull Benzothiazoles: An Atom-Economical Route to Highly Emissive Quadrupolar Arylamine-Functionalized 2,2′-Bibenzothiazoles with Enhanced Two-Photon Absorption
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Copper(II)-catalyzed C-H/C-H coupling of dipolar 2-H-benzothiazoles end-capped with triphenylamine moieties affords highly fluorescent 2,2′-bibenzothiazoles with quadrupolar (D-π-A-π-D) architecture displaying large two-photon absorption (TPA) cross sections (543-1252 GM) in the near-infrared region. The notably higher TPA performance as compared to quadrupolar π-systems with a widely used 2,2′-bipyridine core, along with the ease of the synthesis and chelating N^N ability, makes the title biheteroaryl platform an attractive building block for a large scope of functional dyes exploiting nonlinear optical phenomena.
- Fakis, Mihalis,Georgiou, Dimitris,Gyepes, Róbert,Hrobárik, Peter,Nociarová, Jela,Osusky, Patrik,Polyzos, Ioannis,Smolí?ek, Maro?
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p. 5512 - 5517
(2021/07/31)
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- Are alkynyl spacers in ancillary ligands in heteroleptic bis(diimine)copper(I) dyes beneficial for dye performance in dye-sensitized solar cells?
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The syntheses of 4,40-bis(4-dimethylaminophenyl)-6,60-dimethyl-2,20-bipyridine (1), 4,40-bis(4-dimethylaminophenylethynyl)-6,60-dimethyl-2,20-bipyridine (2), 4,40-bis(4-diphenylaminophenyl)-6,60-dimethyl-2,20-bipyridine (3), and 4,40-bis(4-diphenylaminophenylethynyl)-6,60-dimethyl-2,20-bipyridine (4) are reported along with the preparations and characterisations of their homoleptic copper(I) complexes [CuL2][PF6] (L = 1-4). The solution absorption spectra of the complexes exhibit ligand-centred absorptions in addition to absorptions in the visible region assigned to a combination of intra-ligand and metal-to-ligand charge-transfer. Heteroleptic [Cu(5)(Lancillary)]+ dyes in which 5 is the anchoring ligand ((6,60-dimethyl-[2,20-bipyridine]-4,40-diyl)bis(4,1-phenylene))bis(phosphonic acid) and Lancillary = 1-4 have been assembled on fluorine-doped tin oxide (FTO)-TiO2 electrodes in dye-sensitized solar cells (DSCs). Performance parameters and external quantum efficiency (EQE) spectra of the DSCs (four fully-masked cells for each dye) reveal that the best performing dyes are [Cu(5)(1)]+ and [Cu(5)(3)]+. The alkynyl spacers are not beneficial, leading to a decrease in the short-circuit current density (JSC), confirmed by lower values of EQEmax. Addition of a co-absorbent (n-decylphosphonic acid) to [Cu(5)(1)]+ lead to no significant enhancement of performance for DSCs sensitized with [Cu(5)(1)]+. Electrochemical impedance spectroscopy (EIS) has been used to investigate the interfaces in DSCs; the analysis shows that more favourable electron injection into TiO2 is observed for sensitizers without the alkynyl spacer and confirms higher JSC values for [Cu(5)(1)]+,.
- Becker, Mariia,Constable, Edwin C.,Housecroft, Catherine E.,Risi, Guglielmo
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- Dibenzochrysene derivative compounds and organic light-emitting diode including the same
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PURPOSE: A dibenzochrysene derivative compound is provided to have excellent driving voltage, current efficiency, etc, thereby capable of improving driving voltage of a device and luminous efficiency. CONSTITUTION: A dibenzochrysene derivative compound is represented by chemical formula 1. An organic electroluminescence device comprises an anode, a cathode, and the dibenzochrysene derivative compound between the anode and the cathode. The dibenzochrysene derivative compound is comprised in a light-emitting layer between the anode and the cathode. One or more layer consisting of a hole injection layer, a hole transport layer, an electron block layer, a hole block layer, an electron transport layer, an electron injection layer is comprised between the anode and the cathode.
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- ORGANIC DYES, COMPOSITIONS AND DYE-SENSITIZED SOLAR CELL
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The present invention relates to an organic dye having improved stability to heat, light and water, to a composition comprising the same, and to a dye-sensitized solar cell and, more specifically, to an organic dye represented by chemical formula 1, to a composition comprising the same, and to a dye-sensitized solar cell. The chemical formula 1 is the same as defined in claim 1.COPYRIGHT KIPO 2020
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- Design, synthesis and amplified spontaneous emission of 1,2,5-benzothiadiazole derivatives
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The design, synthesis and evaluation of the amplified spontaneous emission (ASE) properties of a series of arylalkynyl-benzo[c][1,2,5]thiadiazole (BTD) and [1,2,5]thiadiazolo[3,4-g]quinoxaline (TDQ) derivatives are described. The synthetic strategy entailed the use of Sonogashira and Stille reactions based on the different aromatic natures of the two cores. The ASE properties were measured in thin polystyrene (PS) films doped with different concentrations of the synthesised compounds. BTD derivatives showed narrowing of the photoluminescence spectra (PL), thus revealing their potential laser applications. Only one TDQ derivative showed ASE. X-ray diffraction analysis was carried out to understand the observed results and to establish structure-property relationships. Molecules that showed strong molecular packing quenched the PL emission, thus giving rise to higher ASE thresholds. This is the first study in which ASE has been studied in BTD and TDQ derivatives and it represents a step forward in understanding this class of compounds for laser applications.
- Martín, Raúl,Prieto, Pilar,Carrillo, José R.,Rodríguez, Ana M.,De Cozar, Abel,Boj, Pedro G.,Díaz-García, María A.,Ramírez, Manuel G.
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p. 9996 - 10007
(2019/08/21)
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- Mechanofluorochromism, polymorphism and thermochromism of novel D-π-A piperidin-1-yl-substitued isoquinoline derivatives
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Two novel D-π-A isoquinoline derivatives IQ-TPA and IQ-PC using triphenylamine and 9-phenyl-9H-carbazole as an electron donor, respectively, were synthesized to investigate their applications in mechanofluorochromic (MFC) materials. The design was inspire
- Chen, Yating,Zhang, Xinyu,Wang, Mengzhu,Peng, Jingqing,Zhou, Yunbing,Huang, Xiaobo,Gao, Wenxia,Liu, Miaochang,Wu, Huayue
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p. 12580 - 12587
(2019/10/28)
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- Fabrication of Neutral Supramolecular Polymeric Films via Post-electropolymerization of Discrete Metallacycles
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Self-assembly post-modification has proven to be an efficient strategy to build higher-order supramolecular architectures and functional materials. In this study, we successfully realized the construction of a new family of neutral supramolecular polymeric films containing well-defined metallacycles as the main scaffolds through combination of coordination-driven self-assembly with post-electropolymerization. The obtained neutral polymeric materials were fully characterized by the cyclic voltammogram (CV), SEM, and TEM. The thickness of the films was able to be well regulated by the number of scanning cycles. Moreover, we found that the shape of the metallacycles and the number of triphenylamine moieties played important roles in the formation of the final polymer films. We believe that the introduction of the neutral metallacycles into the final polymer structures not only enriches the library of supramolecular polymeric films but also provides a new platform to study neutral molecule detection, separation, and capture.
- Yin, Guangqiang,Chen, Lijun,Wang, Cuihong,Yang, Haibo
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p. 134 - 138
(2017/12/26)
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- Fused compounds and including the organic light-emitting device
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A condensation compound is represented by Formula 1, 2, or 3 where R1 to R24 and A to F are further defined in the detailed description.
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- Heterocyclic compounds, comprising of organic light-emitting device and organic light emitting display
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Heterocyclic compounds, synthetic methods for preparing the same, and organic light-emitting display devices comprising the same are described. The subject heterocyclic compounds may comprise an aromatic ring or a heteroaromatic ring fused with a carbazole, dibenzothiophene, or dibenzofurane derivative, the compounds featuring rigid backbone structures with high glass transition temperatures and high melting points. The subject heterocyclic compounds may exhibit high electrical stability, improved charge transport ability, high heat resistance and improved light-emitting properties when used in organic light-emitting devices. Organic light-emitting display devices prepared according to the present invention exhibit lower driving voltages, increased luminescent efficiencies and longer lifetimes.
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Paragraph 0300; 0324-0328
(2017/09/13)
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- Heterocyclic compound and organic light-emitting device including the same
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A heterocyclic compound represented by Formula 1 below, and an organic light-emitting device including the heterocyclic compound:
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Page/Page column 88
(2017/08/26)
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- Highly selective detection of Cu2+ based on a thiosemicarbazone triphenylacetylene fluorophore
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A novel thiosemicarbazone fluorophore (3) was successfully synthesized in 3 steps via Sonogashira coupling and Knoevenagel condensation using baker's yeast (Saccharomyces cerevisiae) as a biocatalyst. Compound 3 contains triphenylacetylene, which acts as
- Boontom, Sunisa,Boonkitpatarakul, Kanokthorn,Sukwattanasinitt, Mongkol,Niamnont, Nakorn
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p. 2483 - 2487
(2017/04/03)
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- Multi-color photoluminescence induced by electron-density distribution of fluorinated bistolane derivatives
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The aim of this study was to design and develop new fluorinated light-emitting materials with multi-color photoluminescence that are not limited by their states. For this purpose, fluorinated bistolanes with an amino substituent, such as carbazol-9-yl, di
- Yamada, Shigeyuki,Morita, Masato,Konno, Tsutomu
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- Heterocyclic compound and organic light-emitting device including the same
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A heterocyclic compound is represented by Formula 1. An organic light emitting device includes a first electrode, a second electrode and an organic layer between the first and second electrodes. The organic layer includes the heterocyclic compound. An org
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Page/Page column 61-62; 64
(2016/08/07)
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- Easily oxidizable triarylamine materials with naphthalene and binaphthalene core: structure–properties relationship
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We devised and synthesized a series of electron-rich compounds featuring diphenylamine, carbazole or dibenzo[c,g]carbazole connected via phenylacetylene linkers to an aromatic central unit. The key synthetic step was a high yielding cross coupling reaction between halogenated (bi)naphthalene and organometallic reagents prepared in situ from terminal alkynes (side-arms). By masking one of the iodo functions with a diethyltriazenyl group in the side-arm precursors, we efficiently circumvented the formation of doubly aminated by-products. Although one step longer, this approach led to higher yields of terminal alkynes than the direct coupling route. Spectroscopic and electrochemical measurements supported by computational evidence revealed that conjugation in the 1,4-disubstituted naphthalene backbone is superior to the 1,5 or 2,6 substituted cores. The diphenylamine derivative gets oxidized more readily when compared to its carbazole analogs. Expanding the core to binaphthalene did not alter electronic properties, but influenced the physical characteristics significantly.
- Kerner, Luká?,Gmucová, Katarína,Ko?í?ek, Jozef,Pet?í?ek, Václav,Putala, Martin
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p. 7081 - 7092
(2016/10/14)
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- Synthesis, optical, and electrochemical properties, and theoretical calculations of BODIPY containing triphenylamine
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The boron dipyrromethene (BODIPY) triads consisting of two triphenylamine units as electron donor (D) and BODIPY core as electron acceptor (A; B3, and B4) have been synthesized using facile palladium cross-coupling reactions to broaden the absorption of the BODIPY dyes. All dyes and intermediates were characterized by 1H NMR, 11B NMR, 13C NMR, and 19F NMR spectroscopies, UV–Vis spectroscopy, fluorescence spectroscopy, cyclic voltammetry, and time-dependent density functional theory calculations. It was found that an increase in conjugation to the BODIPY core systematically extended the absorption and emission wavelength maxima. As a consequence, B4 containing the D–π–A–π–D structure, exhibited the longest absorption and emission maxima at 597 and 700?nm, respectively, with 1.8?eV in optical bandgap. The 96?nm red-shifted absorption of B4 as compared to the unsubstituted BODIPY (B1) indicated the effective electronic communication between triphenylamine and BODIPY. This suggested that the proper alignment of triphenylamine and BODIPY triad could lead to broader absorption and suitable low energy bandgap. Furthermore, the molecular modeling has been employed to analyze the electronic and optical properties of the dyes. We found that the optical, electrochemical, and theoretical bandgaps of all dyes were in good agreement.
- Wanwong, Sompit,Surawatanawong, Panida,Khumsubdee, Sakunchai,Kanchanakungwankul, Siriluk,Wootthikanokkhan, Jatuphorn
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p. 306 - 315
(2016/10/11)
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- Heterocycle compound and organic light emitting device comprising same
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Provided is a material which has excellent electrical properties, high electrical transport ability, and light emissivity, has high glass transition temperature, and prevents crystallization. Disclosed are a heterocyclic compound of chemical formula 1, and an organic light emitting device including the same. The content of substituents of chemical formula 1 refers to the detailed description.(AA) Second electrode(BB) Electron injection layer(CC) Electron transfer layer(DD) Light emitting layer(EE) Hole transfer layer(FF) Hole injection layer(GG) First electrodeCOPYRIGHT KIPO 2015
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Paragraph 0214; 0215; 0216
(2016/10/10)
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- Boron complex for electroluminescent materials, method for preparing the same and organic light emitting diode comprising the same
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The present invention relates to a boron complex for an organic electroluminescent layer material, a manufacturing method thereof and an organic electroluminescent diode including the same. The boron complex of the present invention can be usefully applied as a red dopant of an electroluminescent layer in an OLED since the boron complex exhibits excellent optical properties such as thermal stability, color purity, luminous efficiency and the like.
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- Novel BODIPY derivative for green organic light-emitting diode dopant and method for preparing the same
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The present invention relates to a novel BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) derivative for a green organic light emitting diode dopant and, more specifically, to a BODIPY derivative for a green organic light emitting diode dopant prepared
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- Triphenylamine-based π-conjugated dendrimers: Convenient synthesis, easy solution processability, and good hole-transporting properties
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Two, third-generation triphenylamine-based dendrimers (DT1 and DT2) were prepared through a simple convergent approach by using a combination of versatile carbon-carbon formation reactions. It is found that the π-linkages connecting the periphery into the core have a pronounced effect on the properties of the material. The introduction of CC bonds in the periphery improves the photophysical behavior and optical qualities of the films in comparison with their introduction in the core of the dendrimer. Both dendrimers exhibit high Tgs (above 240 °C) and high-lying HOMO energy levels of ~5.2 eV. As the hole-transporting layer fabricated through a facile solution process, DT2 can endow an Alq3 based multi-layer OLED device with a maximum brightness of 5020 cd m-2, and a maximum current efficiency of 2.36 cd A-1.
- Li, Zhong'An,Ye, Tenglin,Tang, Sun,Wang, Can,Ma, Dongge,Li, Zhen
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p. 2016 - 2023
(2015/04/27)
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- Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells
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Conjugated systems built by connecting one electron-donor triphenylamine to an electron-withdrawing tetrazine have been prepared using various linkers. We describe here the synthesis, the electrochemical properties and some photophysical properties of the
- Quinton, Cassandre,Alain-Rizzo, Valérie,Dumas-Verdes, Cécile,Clavier, Gilles,Vignau, Laurence,Audebert, Pierre
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p. 9700 - 9713
(2015/12/01)
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- Co-sensitization of N719 with polyphenylenes from the Bergman cyclization of maleimide-based enediynes for dye-sensitized solar cells
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The co-sensitization of N719 with conjugated polyphenylenes for dye-sensitized solar cells (DSSCs) was demonstrated. The conjugated polyphenylenes (6-BC and 7-BC), which contain two triphenylamine (TPA) groups as electron donors and carboxylic acids as ad
- Dong, Luhua,Zheng, Zhiwei,Wang, Youfu,Li, Xing,Hua, Jianli,Hu, Aiguo
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p. 11607 - 11614
(2015/06/02)
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- High performance asymmetrical push-pull small molecules end-capped with cyanophenyl for solution-processed solar cells
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Two novel asymmetrical push-pull small molecules have been synthesized successfully, consisting of triphenylamine and diketopyrrolopyrrole as a fundamental dipolar D-π-A structure with ethynylbenzene as the π-bridge. TPATDPPCN end-capped with cyanophenyl exhibits a low optical band gap of 1.65 eV, and an impressive PCE of 5.94% has been achieved. This journal is the Partner Organisations 2014.
- Gao, Hang,Li, Yanqin,Wang, Lihui,Ji, Changyan,Wang, Yue,Tian, Wenjing,Yang, Xichuan,Yin, Lunxiang
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p. 10251 - 10254
(2014/08/18)
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- Highly efficient and robust blue phosphorescent Pt(II) compounds with a phenyl-1,2,3-triazolyl and a pyridyl- 1,2,4-triazolyl chelate core
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A new class of brightly phosphorescent Pt(II) compounds that contain an NC-chelate phenyl-1,2,3-triazolyl ligand (ptrz) and an NC-chelate pyridyl-1,2,4-triazolyl ligand (pytrz) in the central core is achieved. The impact of various substituent groups on phosphorescence of this class of molecules is examined. Crystal structural analyses revealed that this class of compounds has a great tendency to form stacked dimers-one of which is persistent even in the gas phase-leading to excimer emission. The introduction of bulky substituents, such as diphenyl amino (NPh 2 ) or trityl (CPh 3 ), is found to greatly diminish the excimer emission. Using this approach, several highly effi cient blue and green phosphorescent Pt(II) compounds with λ em at ≈450-460 nm and F φ ≈ 0.70 to 1.00 are obtained. These molecules are highly robust with exceptionally high thermal stability. Bright bluish-green electrophosphorescent devices with external quantum effi ciencies as high as 16.7% are fabricated.
- Wang, Xiang,Gong, Shao-Long,Song, Datong,Lu, Zheng-Hong,Wang, Suning
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p. 7257 - 7271
(2015/02/19)
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- LUMINESCENT COMPOUNDS AND METHODS OF USING SAME
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The invention provides compounds of the general formula (10). The cyclometallating ligand of compound (10) includes an N-donor heterocyclic ligand (2) where at least one X is nitrogen and which is directly bonded to a phenyl group. The phenyl group is ort
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- Tuning two-photon absorption cross-sections for triphenylamine derivatives
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A methylene bridge link connecting the ortho-positions within the triphenylamine scaffold increases the molecular planarity significantly. The one-photon spectroscopies of bridged triphenylamine molecules show considerable extended conjugation relative to their triphenylamine counterparts, leading to enhanced two-photon absorption (TPA) cross-sections. Various substituents at the scaffold have been prepared and studied. Using a femtosecond laser source Z-scan method, the TPA cross-sections were characterized. The maximum magnitude of the TPA cross-section is ~4800 GM, which is four times that of its triphenylamine counterpart. The Royal Society of Chemistry.
- Fang, Zhen,Webster, Richard D.,Samoc, Marek,Lai, Yee-Hing
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p. 17914 - 17917
(2013/10/01)
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- Diacetylene bridged triphenylamines as hole transport materials for solid state dye sensitized solar cells
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We have synthesized and characterized a series of triphenylamine-based hole-transport materials (HTMs), and studied their function in solid-state dye sensitized solar cells (ss-DSSCs). By increasing the electron-donating strength of functional groups (-H -Me -SMe -OMe) we have systematically shifted the oxidation potential and ensuing photocurrent generation and open-circuit voltage of the solar cells. Correlating the electronic properties of the HTM to the device operation highlights a significant energy offset required between the Dye-HTM highest occupied molecular orbital (HOMO) energy levels. From this study, it is apparent that precise control and tuning of the oxidation potential is a necessity, and usually not achieved with most HTMs developed to date for ss-DSSCs. To significantly increase the efficiency of solid-state DSSCs understanding these properties, and implementing dye-HTM combinations to minimize the required HOMO offset is of central importance.
- Planells, Miquel,Abate, Antonio,Hollman, Derek J.,Stranks, Samuel D.,Bharti, Vishal,Gaur, Jitender,Mohanty, Dibyajyoti,Chand, Suresh,Snaith, Henry J.,Robertson, Neil
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p. 6949 - 6960
(2013/07/26)
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- CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DIODE COMPRISING THE SAME
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Embodiments of the present invention are directed to a condensed-cyclic compound represented by Formula 1, and to an organic light-emitting diode including the same.
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- Condensed-cyclic compound and organic light-emitting diode comprising the same
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Embodiments of the present invention are directed to a condensed-cyclic compound represented by Formula 1, and to an organic light-emitting diode including the same.
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- Multistate redox-active metalated triarylamines
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trans-[(η5-C5H5)Fe(η5- C5H4-η1-C≡C)Ru(C≡C-4-C 6H4NPh2)(dppe)2] [4; dppe = 1,2-bis(diphenylphosphanyl)ethane] and trans,trans,trans-[{(
- Grelaud, Guillaume,Cifuentes, Marie P.,Schwich, Torsten,Argouarch, Gilles,Petrie, Simon,Stranger, Rob,Paul, Frederic,Humphrey, Mark G.
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- Symmetrical and unsymmetrical multibranched D-π-A molecules based on 1,3,5-triazine unit: Synthesis and photophysical properties
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A series of V-shaped (D-π-A-π-D) and star-shaped ((D-π-) 3A) molecules based on the electron acceptor 1,3,5-triazine core (A) connected to different electron donor groups (D) by a carbon-carbon triple bond as a conjugation bridge (π) has been synthesized. The studied molecules can be separated into symmetrically and unsymmetrically substituted molecules depending on the combination of the electron donating branches connected to the triazine core. Their photophysical properties are characterized experimentally and the structure-properties relationship is analysed with the aid of theoretical calculations. The symmetrically branched 1,3,5-triazine-based molecules exhibit similar UV-vis absorption to the corresponding linear molecules, but an obvious blue-shift in the emission is observed with increasing dimensionality. The absorption of the unsymmetrically branched 1,3,5-triazine-based molecules is clearly localized on a specific branch, suggesting a weak interbranch conjugation in the ground state. Emission is mainly controlled by the branch with the lowest energy excited state, which corresponds to the one with the largest intramolecular charge transfer (ICT) effect. The two-photon absorption properties of selected molecules are studied. They exhibit strong two-photon absorption activities and a modest interbranch conjugation effect, enhancing the TPA cross-section beyond the additive effect of increasing branch number. The Royal Society of Chemistry 2012.
- Zhang, Liqian,Zou, Li,Xiao, Jiang,Zhou, Pengcheng,Zhong, Cheng,Chen, Xingguo,Qin, Jingui,Mariz, Ines F. A.,MacOas, Ermelinda
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p. 16781 - 16790
(2012/10/29)
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- Dihalo-substituted dibenzopentalenes: Their practical synthesis and transformation to dibenzopentalene derivatives
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Diiodo- and bromo, iodo-substituted dibenzopentalenes were obtained by treatment of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene with I2 and IBr, respectively. These dihalo-substituted pentalenes reacted with terminal ethynes in Sonogashira co
- Xu, Feng,Peng, Lifen,Orita, Akihiro,Otera, Junzo
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p. 3970 - 3973
(2012/10/08)
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- Tuning the photophysical properties of N∧N Pt(II) bisacetylide complexes with fluorene moiety and its applications for triplet-triplet- annihilation based upconversion
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Fluorene-containing aryl acetylide ligands were used to prepare N∧N Pt(ii) bisacetylide complexes, where aryl substituents on the fluorene are phenyl (Pt-1), naphthal (Pt-2), anthranyl (Pt-3), pyrenyl (Pt-4), 4-diphenylaminophenyl (Pt-5) and 9,9-di-n-octylfluorene (Pt-6) (where N∧N ligand = 4,4′-di-tert-butyl-2,2′-bipyridine, dbbpy). All the complexes show room temperature (RT) phosphorescence. The emissive T1 excited states of Pt-1, Pt-5 and Pt-6 were assigned as metal-to-ligand-charge- transfer state (3MLCT), whereas for Pt-2, Pt-3 and Pt-4, the emissive T1 excited states were identified as the intraligand state ( 3IL), based on steady state emission spectra, the lifetime of the T1 state, emission spectra at 77 K, spin density analysis and the time-resolved transient absorption spectroscopy. Exceptionally long lived T 1 excited state was observed for Pt-3 (τ = 66.7 μs) and Pt-4 (τ = 54.7 μs), compared to a model complex dbbpy Pt(ii) Bisphenylacetylide (τ = 1.25 μs). RT phosphorescence of anthracene was observed at 780 nm with Pt-3. The critical role of the fluorene is to move the absorption of the complexes to the red-end of the spectra, but at the same time, without compromising the energy level of the T1 state of the complexes. The advantage of this unique spectral tuning effect and the long-lived T1 excited states of Pt-4 was demonstrated by the enhanced performance of the complexes as triplet sensitizers for triplet-triplet annihilation (TTA) based upconversion; an upconversion quantum yield (ΦUC) up to 22.4% was observed with Pt-4 as the sensitizer. Other complexes described herein show negligible upconversion. The high upconversion quantum yield of Pt-4 is attributed to its intense absorption of visible light and long-lived T1 excited state. Based on the result of Pt-4, we propose that weakly phosphorescent, or non-phosphorescent transition metal complexes can be used as triplet sensitizers for TTA upconversion, compared to the phosphorescent triplet sensitizers currently used for TTA upconversion. Our results will be useful for the design of transition metal complexes to enhance the light-absorption and thereafter the cascade photophysical processes, without decreasing the T1 excited state energy levels, which are important for the application of the complexes as triplet sensitizers in various photophysical processes. The Royal Society of Chemistry 2012.
- Li, Qiuting,Guo, Huimin,Ma, Lihua,Wu, Wanhua,Liu, Yifan,Zhao, Jianzhang
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supporting information; experimental part
p. 5319 - 5329
(2012/05/20)
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- Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: A route to triphenylamine-based chromophores with enhanced two-photon absorption
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A series of dipolar and octupolar triphenylamine-derived dyes containing a benzothiazole positioned in the matched or mismatched fashion have been designed and synthesized via palladium-catalyzed Sonogashira cross-coupling reactions. Linear and nonlinear optical properties of the designed molecules were tuned by an additional electron-withdrawing group (EWG) and by changing the relative positions of the donor and acceptor substituents on the heterocyclic ring. This allowed us to examine the effect of positional isomerism and extend the structure-property relationships useful in the engineering of novel heteroaromatic-based systems with enhanced two-photon absorption (TPA). The TPA cross-sections (δTPA) in the target compounds dramatically increased with the branching of the triphenylamine core and with the strength of the auxiliary acceptor. In addition, a change from the commonly used polarity in push-pull benzothiazoles to a reverse one has been revealed as a particularly useful strategy (regioisomeric control) for enhancing TPA cross-sections and shifting the absorption and emission maxima to longer wavelengths. The maximum TPA cross-sections of the star-shaped three-branched triphenylamines are ~500-2300 GM in the near-infrared region (740-810 nm); thereby the molecular weight normalized δTPA/MW values of the best performing dyes within the series (2.0-2.4 GM?g-1?mol) are comparable to those of the most efficient TPA chromophores reported to date. The large TPA cross-sections combined with high emission quantum yields and large Stokes shifts make these compounds excellent candidates for various TPA applications, including two-photon fluorescence microscopy.
- Hrobarik, Peter,Hrobarikova, Veronika,Sigmundova, Ivica,Zahradnik, Pavol,Fakis, Mihalis,Polyzos, Ioannis,Persephonis, Peter
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p. 8726 - 8736
(2012/01/05)
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- Tuning the emission colour of triphenylamine-capped cyclometallated platinum(II) complexes and their application in luminescent oxygen sensing and organic light-emitting diodes
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[(Aryl-ppy)Pt(acac)] (ppy = 2-phenylpyridine, acac = acetylacetonato) derivatives with triphenylamine (TPA) substituents on the ppy ligand have been prepared. The TPA fragment is either directly cyclometallated (Pt-1) or attached to the ppy ligand through a C-C single bond (Pt-2) or a novel α-diketo group (Pt-3). All the complexes show room-temperature phosphorescence in fluid solution with emission bands in the range of 530-590 nm, which are red-shifted relative to the model complex [ppyPt(acac)] (λem = 486 nm). This emission colour tuning effect is attributed to either an elevated HOMO energy caused by electron-donating TPA substituents on the ppy ligand or a decreased LUMO energy caused by the electron-trap effect of electron-withdrawing substituents; both result in a smaller HOMO-LUMO energy gap and thus red-shifted emission. The complexes show extended luminescence lifetimes (τ = 3.0-5.5 μs) relative to the parent complex [ppyPt(acac)] (τ = 2.6 μs). The luminescent oxygen-sensing properties of the complexes were studied in solution and polymer films. White light emission was observed with an OLED device fabricated with complex Pt-3 with CIE coordinates of (0.32, 0.32). [(Aryl-ppy)Pt(acac)] complexes have been prepared that show room-temperature phosphorescence at 490-590 nm. The emission colour tuning effect is attributed to either the elevated HOMO energy or the decreased LUMO energy. The luminescent O2-sensing properties of the complexes in polymer films were studied. A white light-emitting OLED was fabricated with Pt-3 with a CIE of (0.32, 0.32).
- Wu, Wenting,Cheng, Chuanhui,Wu, Wanhua,Guo, Huimin,Ji, Shaomin,Song, Peng,Han, Keli,Zhao, Jianzhang,Zhang, Xin,Wu, Yubo,Du, Guotong
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p. 4683 - 4696
(2011/02/28)
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- Aromatic fumaronitrile core-based donor-linker-acceptor-linker-donor (D-π-A-π-D) compounds: Synthesis and hotophysical properties
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A new class of aromatic fumaronitrile core-based compounds with different donors and linkers has been synthesized and well characterized. Compounds 1 and 2 have indole and 2-phenylindole groups as electron donors, respectively. Compounds 3 and 4 have a diphenylamino group as the electron donor, and compound 5 has a 3,6-di-tert-butylcarbazole group as an electron donor. These compounds absorb in the blue-to-green region and emit in the blue-to-red region depending on the electron donor, linker, and solvents. The quantum yields of fluorescence of these compounds in solution are measured and found to be moderate, but in solid states, they are high. These compounds display strong emission solvatochromism that is reflected by a large shift in their fluorescence emission maxima on changing the solvents. This change is accompanied by a successive decrease in fluorescence intensity. The fluorescence lifetimes of these compounds are measured in different solvent and found to vary from 1 to 7 ns. Optical switching of these compounds with solvents, concentration, and excitation energy have been studied. The correlation between the functional group and optical properties has been established to some extent. The ability of these compounds to function as colorimetric and luminescence pH sensors is demonstrated with color changes and luminescence switching upon the addition of trifluoroacetic acid. The potentiality of these compounds for application in optoelectronics has been optically assessed.
- Panthi, Krishna,Adhikari, Ravi M.,Kinstle, Thomas H.
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scheme or table
p. 4542 - 4549
(2010/08/05)
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- Synthesis and computational studies of diphenylamine donor-carbazole linker-based donor-acceptor compounds
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The design, synthesis, and electronic spectra of a novel series of organic diphenylamine donor-carbazole linker-based donor-acceptor compounds are reported. The low-lying electronic transitions in these compounds are investigated using a combination of conventional steady-state absorption spectroscopy and tools of computational photochemistry. The electronic transitions were found to depend both on the nature of the acceptor moiety and the presence/absence of a carbazole linker, not affected by the presence of the trifluoromethlyphenyl group in all the reported DA compounds.
- Panthi, Krishna,El-Khoury, Patrick Z.,Tarnovsky, Alexander N.,Kinstle, Thomas H.
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scheme or table
p. 9641 - 9649
(2011/02/22)
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- Benzothiazole-based fluorophores of donor-π-acceptor-π-donor type displaying high two-photon absorption
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A series of novel heterocycle-based dyes with donor-π-bridge-acceptor- π-bridge-donor (D-π-A-π-D) structural motif, where benzothiazole serves as an electron-withdrawing core, have been designed and synthesized via palladium-catalyzed Sonogashira and Suzuki-type cross-coupling reactions. All the target chromophores show strong one-photon and two-photon excited emission. The maximum two-photon absorption (TPA) cross sections ΔTPA of the prepared derivatives bearing diphenylamino functionalities occur at wavelengths ranging from 760 to 800 nm and are as large as ~900-1100 GM. One- and two-photon absorption characteristics of the title dyes have also been investigated by using density functional theory (DFT) and the structure-property relationships are discussed. The TPA cross sections calculated by means of quadratic response time-dependent DFT using the Coulomb-attenuated CAM-B3LYP functional support the experimentally observed trends within the series, as well as higher ΔTPA values of the title compounds compared to those of analogous fluorene or carbazole-derived dyes. In contrast, the traditional B3LYP functional was not successful in predicting the observed trend of TPA cross sections for systems with different central cores. In general, structural modification of the π-bridge composition by replacement of ethynylene (alkyne) with E-ethenylene (alkene) linkages and/or replacement of dialkylamino electron-donating edge substituents by diarylamino ones results in an increase of ΔTPA values. The combination of large TPA cross sections and high emission quantum yields makes the title benzothiazole-based dyes attractive for applications involving two-photon excited fluorescence (TPEF).
- Hrobarikova, Veronika,Hrobarik, Peter,Gajdos, Peter,Fitilis, Ioannis,Fakis, Mihalis,Persephonis, Peter,Zahradnik, Pavol
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experimental part
p. 3053 - 3068
(2010/07/15)
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- Synthesis, crystal structures, and photophysical properties of triphenylamine-based multicyano derivatives
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A new series of intramolecular charge transfer (ICT) molecules were synthesized by attaching various strong electron-withdrawing groups to a triphenylamine backbone. Relationships between chemical structures and optoelectronic properties of these compound
- Tang, Xianglin,Liu, Weimin,Wu, Jiasheng,Lee, Chun-Sing,You, Juanjuan,Wang, Pengfei
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experimental part
p. 7273 - 7278
(2011/02/22)
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- Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes
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A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of β-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH2Cl2, resulting in high quantum yields.
- Fang, Jing-Kun,An, De-Lie,Wakamatsu, Kan,Ishikawa, Takeharu,Iwanaga, Tetsuo,Toyota, Shinji,Matsuo, Daisuke,Orita, Akihiro,Otera, Junzo
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supporting information; experimental part
p. 917 - 920
(2010/05/03)
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- Synthesis and spectroscopic study of phenylenee (poly) ethynylenes substituted by amino or amino/cyano groups at terminal(s):Electronic effect of cyano group on charge-transfer excitation of acetylenic φ-systems
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To gain insight into substituent electronic effect on charge-transfer excitation of acetylenic p-systems, phenylenee(poly)ethynylenes substituted by Ph2N or Ph2N/cyano groups were synthesized by combination of Sonogashira coupling and double elimination protocol of b-substituted sulfones.These substituted phenyleneethynylenes showed large molar absorption coefficients 3, and emitted strong fluorescence upon UV light irradiation.Phenylenee(poly)ethynylenes, which involve butadiyne or hexatriyne motifs, emitted fluorescence in remarkably lower fluorescence quantum yields FF as their polyethynylene motifs e(C^C)ne expanded.The drastic decrease of fluorescence quantum yields FF were explained in terms of increasing nonradiative reaction rate constants knr, which had been determined by the corresponding fluorescence quantum yields F F and lifetime values s.The emission underwent a large bathochromic shift in polar solvents because the charge-separated excited state is more stabilized than the ground state.Comparison of slope values r in Lippert/Mataga plot for the Ph2N and Ph2N/cyano-substituted phenylenee(poly)ethynylenes revealed that the latter underwent large change of dipole moments upon photo-excitation although highly expanded acetylenic p-systems with cyano group did little.
- Fang, Jing-Kun,An, De-Lie,Wakamatsu, Kan,Ishikawa, Takeharu,Iwanaga, Tetsuo,Toyota, Shinji,Akita, Shin-Ichi,Matsuo, Daisuke,Orita, Akihiro,Otera, Junzo
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scheme or table
p. 5479 - 5485
(2010/08/19)
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