- Tuning optical and electronic properties of poly(4,4'-triphenylamine vinylene)s by post-modification reactions
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New triphenylamine-based polyarylenevinylenes with pendant phenylethynyl- and 3-pyridylethynyl substituents were synthesized by Stille polycondensation of trans-1,2-bis(tributylstannyl)ethene with two new ethynyl substituted triphenylamine monomers, i.e., N,N-bis(4-iodophenyl)-4'-(phenylethynyl) phenylamine and N,N-bis(4-iodophenyl)-4'-(3-pyridylethynyl) phenylamine. The polymers were characterized by spectral methods and cyclic voltammetry and their properties were compared with those of the unsubstituted poly(4,4'-triphenylamine vinylene). Chemical post-modifications of the polymers by tetracyanoethylene addition to the triple bond, and quaternization of pyridyl group with accent on the fine-tuning of the optical and electrochemical properties were also studied. Density functional theory calculations provide a reliable interpretation of the observed spectra and electrochemical data.
- Grigoras, Mircea,Catargiu, Ana Maria,Ivan, Teofilia,Vacareanu, Loredana,Minaev, Boris,Stromylo, Evgeniy
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- Synthesis, characterization and charge-discharge studies of ferrocene-containing poly(fluorenylethynylene) derivatives as organic cathode materials
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Two new poly(fluorenylethynylene)s with ferrocene moieties PFFAL1 and PFFAL2 were designed and synthesized. Their structures, molar masses, photophysical properties and thermal characteristics were analyzed by 1H NMR, Fourier transform infrared
- Xiang, Jing,Burges, René,H?upler, Bernhard,Wild, Andreas,Schubert, Ulrich S.,Ho, Cheuk-Lam,Wong, Wai-Yeung
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- Acid-induced tunable white light emission based on triphenylamine derivatives
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A series of triphenylamine (TPA) derivatives with various substituent groups were prepared and showed different absorption and fluorescence characteristics due to the substituent effect. On account of the existence of pyridine units, these TPA derivatives exhibited acid-induced tunable multicolor fluorescence emission including white light emission. In addition, acid-induced fluorescence regulation of these compounds has been also realized in the solid state, which enable them to be successfully constructed the stimuli-responsive fluorescent films and fluorescent inks for inkjet printing.
- Liu, Xi,Qin, Yi,Zhu, Junlong,Zhao, Xiaoli,Cheng, Tanyu,Jiang, Yanrong,Sun, Haitao,Xu, Lin
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supporting information
p. 1537 - 1540
(2020/11/12)
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- Synthesis and photophysical properties of fluorescent dyes based on triphenylamine, diphenylamine, diphenyl sulfone or triphenyltriazine derivatives containing an acetylene linkage group
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In this study, ten fluorescent dyes were prepared based on three different kinds of central moiety, such as triphenylamine, diphenylsulfone or triphenyltriazine, which was coupled to either carbazole or naphthalimidinyl group via an acetylene linkage group. N-n-Butyl-carbazole, N-phenyl-carbazole or N-n-butyl-naphthalimide was coupled to the individual central moiety of triphenylamine, diphenyl sulfone, 2,4,6-triphenyl-1,3,5-trazine or diphenylamine using a Sonogashira coupling reaction in the final step. All dyes were confirmed their chemical structure by 1H NMR, GC-Mass and elemental analyses. The absorption properties and thermal stabilities of the fluorescent dyes were examined. Density Functional Theory (DFT) and Time-Dependent DFT calculations were carried out, in addition to geometry simulation, by using the Gaussian 09 program. In terms of fluorescence properties in this series, two dyes based on diphenyl sulfonyl and three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-carbazole exhibited a blue emission, whereas three dyes based on triphenylamine substituted by 1–3 of N-n-butyl-naphthalimide were observed by a red emitter which can be attributable to both effects the bathochromic shifts in absorption maxima and larger Stokes shifts. In case of corresponding 2,4,6-triphenyl-1,3,5-trazine central moiety coupled to a carbazole ring, a green fluorescence was emitted. Results revealed that the fluorescence of the dyes is affected by the electron-donating strength of the acetylene linkages involved in the π-conjugation systems of the dyes.
- Ahn, Sung-Ok,Choi, Jae-Hong,Kim, Kyung-Won,Kwon, Su-Hyeon,Lee, Byung-Jun,Lee, Ju-Hong
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- Multipodal arrangement of push-pull chromophores: a fundamental parameter affecting their electronic and optical properties
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A series of model push-pull molecules with linear, quadrupolar, and tripodal arrangements, a varyingly substituted amino donor, two acceptors, and a partially extended π-system has been prepared. Two peripheral electron acceptors, namely N,N′-dibutylbarbituric acid and dicyanovinyl, were employed. The fundamental properties of 24 push-pull chromophores were investigated by differential scanning calorimetry, electrochemistry, one-photon absorption spectroscopy, photoinduced piezooptics, and were supported by DFT calculations. Thorough structure-property relationships were elucidated, while a significant influence of the structural arrangement/branching on the electronic and optical properties has been revealed. The fundamental optoelectronic properties of push-pull molecules are affected by their arrangement (linear/quadrupolar/tripodal), the peripheral acceptor attached, extension and planarization of the π-system, and also by the type of auxiliary N-substituent.
- Klikar,Kityk,Kulwas,Mikysek,Pytela,Bure?
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supporting information
p. 1459 - 1472
(2017/02/23)
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- Solvent and branching effect on the two-photon absorption properties of push-pull triphenylamine derivatives
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The photophysical and two-photon absorption (2PA) properties of two tri-podal molecules and of their quadrupolar and dipolar counterparts are reported for a series of solvents with varying polarity. The molecules possess a tri-phenylamine electron donating group and mono-cyano acceptors while olefinic and acetylenic π-linkers have been used. Branching led to an increase of the molar extinction coefficient and to a slight bathochromic shift of the absorption spectra while the fluorescence quantum yields decrease but they are maintained to relatively high values. Solvatochromic measurements in the tri-podal molecules revealed an emitting state with a polar nature. The 2PA cross sections in general increase upon branching but the observed behaviour strongly depends on the type of solvent. The highest 2PA cross sections are obtained in solvents of medium polarity and values as high as 1420 GM are reported.
- Cvejn,Michail,Seintis,Klikar,Pytela,Mikysek,Almonasy,Ludwig,Giannetas,Fakis,Bure?
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p. 12819 - 12828
(2016/02/12)
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- Triphenylamine derivatized phenylacetylene macrocycle with large two-photon absorption cross-section
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A phenylacetylene macrocycle (PAM) derivative containing triphenylamine as the framework was synthesized in one-step Sonogashira coupling. The photophysical and electrochemical properties were investigated in details. This hexamer shows significant enhanc
- Fang, Zhen,Samoc, Marek,Webster, Richard D.,Samoc, Anna,Lai, Yee-Hing
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supporting information; experimental part
p. 4885 - 4888
(2012/09/07)
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- Synthesis, two-photon absorption, and optical power limiting of new linear and hyperbranched conjugated polyynes based on bithiazole and triphenylamine
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Two new linear and hyperbranched conjugated polymers P1 and P2 have been synthesized by Sonogashira coupling reaction, in which the main chain consists of bithiazole moieties as electron acceptors and triphenylamino groups as donors. The conjugated polymers were characterized by TGA, UV-vis absorption, fluorescence emission, electrochemical cyclic voltammetry, and two-photon absorption measurements. They exhibited excellent solubility in organic solvents and high thermal stability (5% of weight loss at 299 °C). The two-photon absorption cross sections (σ) measured by the open aperture Z-scan technique using 140 femtosecond (fs) pulse were determined to be 1014 and 552 GM per repeating unit for P1 and P2, respectively. This result shows that the σ of linear conjugated P1 is higher than that of hyperbranched P2, indicating that the linear polymer offers better intramolecular charge transfer ability. In THF, P1 and P2 exhibit intense frequency up-converted fluorescence under the excitation of 140 fs pulses at 800 nm with the peaks located at 580 and 548 nm, respectively. Meanwhile, the optical limiting behaviors for the polymers were studied by using a focused 800 nm laser beam of 140 fs duration. It was found that these polymers also exhibit good optical-limiting properties and make them potential candidates for optical limiters in the photonic fields.
- Jiang, Yihua,Wang, Yaochuan,Yang, Jiabao,Hua, Jianli,Wang, Bing,Qian, Shiqiong,Tian, He
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experimental part
p. 1830 - 1839
(2012/03/10)
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