- Molecular Engineering of Potent Sensitizers for Very Efficient Light Harvesting in Thin-Film Solid-State Dye-Sensitized Solar Cells
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Dye-sensitized solar cells (DSSCs) have shown significant potential for indoor and building-integrated photovoltaic applications. Herein we present three new D-A-A organic sensitizers, XY1, XY2, and XY3, that exhibit high molar extinction coefficients and a broad absorption range. Molecular modifications of these dyes, featuring a benzothiadiazole (BTZ) auxiliary acceptor, were achieved by introducing a thiophene heterocycle as well as by shifting the position of BTZ on the conjugated bridge. The ensuing high molar absorption coefficients enabled the fabrication of highly efficient thin-film solid-state DSSCs with only 1.3 μm mesoporous TiO2 layer. XY2 with a molar extinction coefficient of 6.66 × 104 M-1 cm-1 at 578 nm led to the best photovoltaic performance of 7.51%.
- Zhang, Xiaoyu,Xu, Yaoyao,Giordano, Fabrizio,Schreier, Marcel,Pellet, Norman,Hu, Yue,Yi, Chenyi,Robertson, Neil,Hua, Jianli,Zakeeruddin, Shaik M.,Tian, He,Gr?tzel, Michael
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- Butterfly-Like Triarylamines with High Hole Mobility and On/Off Ratio in Bottom-Gated OFETs
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Highly π-extended butterfly-shaped triarylamine dyads with aryleneethynylene spacer were constructed using an efficient synthetic route. These aryleneethynylene-bridged dyads are highly fluorescent and exhibited high HOMO levels, and low bandgaps, which a
- Devibala, Panneerselvam,Balambiga, Balu,Mohamed Imran, Predhanekar,Bhuvanesh, Nattamai S. P.,Nagarajan, Samuthira
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supporting information
p. 15375 - 15381
(2021/10/06)
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- Organic small molecule hole injection/transport material and preparation method and application thereof
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The invention belongs to the technical field of organic small molecule hole injection/transport materials, and discloses an organic small molecule hole injection/transport material and a preparation method and application thereof. A structural formula of the organic small molecule hole injecting/transporting material is as shown in the specification, wherein Ar1, Ar2 and Ar3 are independently unsubstituted benzene ring, fused ring or spiro ring aromatic hydrocarbons, or independently benzene ring, fused ring or spiro ring aromatic hydrocarbons substituted by an alkyl group, an alkoxy group oran alkylthio group with a carbon atom number of 1-6 respectively, and a carbon atom number of the benzene ring, fused ring or spiro ring aromatic hydrocarbons is 6-40. A plurality of non-planar structure arylamine units are adopted, and methoxy end groups are introduced, so that the material has high thermal stability, high glass transition temperature, high HOMO energy level, high hole mobility and good solubility, and has important application prospects in optoelectronic devices.
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Paragraph 0065; 0069-0071
(2019/11/14)
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- Halogen-substituted triphenylamine derivatives with intense mechanoluminescence properties
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Three triphenylamine (TPA) derivatives, constructed by the introduction of halogen atoms in TPA, show strong mechanoluminescence emissions, partially due to their various electronic configurations by virtue of the electron withdrawing ability of halogen atoms. Careful investigation of their single crystals and the density functional theory (DFT) calculations based on the crystal structure demonstrate that the enhanced intermolecular interactions and the twisted molecular structure contribute to their strong ML emission.
- Tu, Jin,Fan, Yunhao,Wang, Jiaqiang,Li, Xiaoyu,Liu, Fan,Han, Mengmeng,Wang, Can,Li, Qianqian,Li, Zhen
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supporting information
p. 12256 - 12262
(2019/10/22)
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- Positive charge-dependent cell targeted staining and DNA detection
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The chemical structures or positive charge-guided specific cell organelles' staining was an interesting but very challenging research work. In this paper, we synthesized a series of triphenylamine (TPA) derivatives with mono-, di- and tri-pyridinium as su
- Yin, Pei,Wang, Tao,Yang, Yuan,Yin, Weidong,Zhang, Shaoxiong,Yang, Zengming,Qi, Chunxuan,Ma, Hengchang
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supporting information
p. 18251 - 18258
(2019/12/02)
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- Thiophene insertion for continuous modulation of the photoelectronic properties of triphenylamine-based metal-organic frameworks for photocatalytic sulfonylation-cyclisation of activated alkenes
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Pharmaceutically meaningful conversions like photocatalytic sulfonylation call for the precise control of the photoelectronic properties of photocatalysts. A ligand engineering strategy of inserting different numbers of thiophenes into the scaffold of triphenylamine (TPA)-based ligands was developed to improve the visible light absorption, enhance the oxidation potentials of the ground states, and decrease the reduction potentials of the excited states, providing a powerful tool for continuous modulation of the photoelectronic properties of metal-organic framework (MOF)-based heterogeneous photocatalysts. The ligand inserted with two thiophenes was found to possess a well-balanced photoelectronic performance, endowing the corresponding MOF Zn-BCTA with good visible light-harvesting ability and a moderate excited-state reduction potential with minimal over-potential for the photoinduced generation of sulfonyl radicals while avoiding the competitive over-reduction of the sulfonyl moieties. The breaking of the C3-symmetry of the TPA-based ligand forged a distorted coordination geometry of the Zn4O nodes of the MOF to provide potential active sites to facilitate the fixation and activation of α,β-unsaturated carbonyl substrates, and the two-fold interpenetrated frameworks further enhanced the spatial proximity between the encapsulated substrate and the photoredox-active centre. The synergy of the well-tuned photoelectronic properties of Zn-BCTA and the spatial confinement effect within the pores benefited the tandem sulfonylation-cyclisation of unsaturated alkenes in an efficient and diastereoselective mode for the construction of bio-interesting sulphoyl isoquinolinediones/oxindoles.
- Zhang, Tiexin,Shi, Yusheng,Zhang, Sen,Jia, Chen,He, Cheng,Duan, Chunying
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supporting information
p. 18448 - 18457
(2018/11/23)
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- Pyran-annulated perylene diimide derivatives as non-fullerene acceptors for high performance organic solar cells
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There has been growing interest in the effectual strategy of constructing non-fullerene acceptors for organic solar cells that may overcome the defect of traditional fullerene-based acceptors. Herein, two novel push-pull (acceptor-donor-acceptor) type sma
- Li, Gang,Zhang, Yu,Liu, Tao,Wang, Shuaihua,Li, Dandan,Li, Jiewei,Li, Fengting,Yang, Lian-Ming,Luo, Zhenghui,Yang, Chuluo,Yan, He,Hao, Pin,Shang, Qiaoyan,Tang, Bo
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supporting information
p. 11111 - 11117
(2018/11/03)
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- Photo-irradiated: E / Z isomerization reaction of star-shaped isomers containing two cyanostilbene arms with charge transfer excited states
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The E/Z isomerization reaction of the multi-cyanostilbene molecule is still not clear. Herein, we have designed and synthesized three star-shaped molecular isomers with a triphenylamine core linked to two cyanostilbene groups with E/Z isomerization, Z,Z-TPDCF, Z,E-TPDCF and E,E-TPDCF, possessing three different isomeric molecular configurations, to investigate the specific E/Z isomerization reaction of the cyanostilbene groups in the two molecular arms. The in situ UV, 1H NMR and HPLC spectra under UV-irradiation clearly showed that the E/Z isomerization reactions of both E,E-TPDCF and Z,Z-TPDCF firstly turned them into Z,E-TPDCF, and the Z,E-TPDCF was almost simultaneously turned into more E,E-TPDCF and less Z,Z-TPDCF due to the calculated lowest unoccupied molecular orbitals of Z,E-TPDCF on the cyanostilbene arm with the Z-configuration. In general, Z,E-TPDCF exhibited a relatively better configurational stability than Z,Z-TPDCF or E,E-TPDCF under the photo-irradiation conditions. Further research demonstrated that all three isomers exhibited excellent aggregation-induced emission (AIE) properties.
- Liu, Jin,Li, Weijun,Liu, Minjie,Dong, Yujie,Dai, Yuyu,Song, Qingbao,Wang, Jianli,Zhang, Cheng
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p. 28279 - 28286
(2018/11/25)
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- Aggregation-induced emission (AIE)-active fluorescent probes with multiple binding sites toward ATP sensing and live cell imaging
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Aggregation-induced emission (AIE)-active compounds are attractive fluorescent materials for applications in chemical and biological sensing. The AIE effect of such materials amplifies changes in the fluorescence signal due to the physical state transformation from aggregation to disaggregation, which can be employed for detecting various analytes with high sensitivity. In particular, specific bio-active analyte recognition is not only very interesting but also challenging. In this paper, we report a set of novel AIE-active fluorescent probes containing pyridiniums and boric acid groups (TPA-PP, TPA-PPA-1, TPA-PPA-2, TPA-PPA-3), which has been developed for adenosine 5′-triphosphate (ATP) recognition. These probes with two types of interaction modes and multiple connection sites toward ATP molecules are able to selectively discriminate ATP among other bioactive anions with a significant enhancement in fluorescence emission. In particular, in the application of cell imaging, as the number of positive charges and boric acid group increased further, the probes could penetrate into cells, and then enter into the nucleus very specifically. These results clearly demonstrate that the newly developed sensors are suitable for specific tracing of different cell organelles with a height visualization and retention ability. Therefore, all of them are confirmed as promising alternatives for live cell imaging in the future.
- Ma, Hengchang,Yang, Manyi,Zhang, Caili,Ma, Yucheng,Qin, Yanfang,Lei, Ziqiang,Chang, Lu,Lei, Lei,Wang, Tao,Yang, Yuan
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supporting information
p. 8525 - 8531
(2017/11/15)
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- Synthesis and Exciton Dynamics of Donor-Orthogonal Acceptor Conjugated Polymers: Reducing the Singlet-Triplet Energy Gap
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The presence of energetically low-lying triplet states is a hallmark of organic semiconductors. Even though they present a wealth of interesting photophysical properties, these optically dark states significantly limit optoelectronic device performance. Recent advances in emissive charge-transfer molecules have pioneered routes to reduce the energy gap between triplets and "bright" singlets, allowing thermal population exchange between them and eliminating a significant loss channel in devices. In conjugated polymers, this gap has proved resistant to modification. Here, we introduce a general approach to reduce the singlet-triplet energy gap in fully conjugated polymers, using a donor-orthogonal acceptor motif to spatially separate electron and hole wave functions. This new generation of conjugated polymers allows for a greatly reduced exchange energy, enhancing triplet formation and enabling thermally activated delayed fluorescence. We find that the mechanisms of both processes are driven by excited-state mixing between π-πand charge-transfer states, affording new insight into reverse intersystem crossing.
- Freeman, David M. E.,Musser, Andrew J.,Frost, Jarvist M.,Stern, Hannah L.,Forster, Alexander K.,Fallon, Kealan J.,Rapidis, Alexandros G.,Cacialli, Franco,McCulloch, Iain,Clarke, Tracey M.,Friend, Richard H.,Bronstein, Hugo
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supporting information
p. 11073 - 11080
(2017/08/21)
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- A search for blues brothers: X-ray crystallographic/spectroscopic characterization of the tetraarylbenzidine cation radical as a product of aging of solid magic blue
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Magic blue (MB+? SbCl6- salt), i.e. tris-4-bromophenylamminium cation radical, is a routinely employed one-electron oxidant that slowly decomposes in the solid state upon storage to form so called 'blues brothers', which often complicate the quantitative analyses of the oxidation processes. Herein, we disclose the identity of the main 'blues brother' as the cation radical and dication of tetrakis-(4-bromophenyl)benzidine (TAB) by a combined DFT and experimental approach, including isolation of TAB+? SbCl6- and its X-ray crystallography characterization. The formation of TAB in aged magic blue samples occurs by a Scholl-type coupling of a pair of MB followed by a loss of molecular bromine. The recognition of this fact led us to the rational design and synthesis of tris(2-bromo-4-tert-butylphenyl)amine, referred to as 'blues cousin' (BC: Eox1 = 0.78 V vs. Fc/Fc+, λmax(BC+?) = 805 nm, εmax = 9930 cm-1 M-1), whose oxidative dimerization is significantly hampered by positioning the sterically demanding tert-butyl groups at the para-positions of the aryl rings. A ready two-step synthesis of BC from triphenylamine and the high stability of its cation radical (BC+?) promise that BC will serve as a ready replacement for MB and an oxidant of choice for mechanistic investigations of one-electron transfer processes in organic, inorganic, and organometallic transformations.
- Talipov, Marat R.,Hossain, Mohammad M.,Boddeda, Anitha,Thakur, Khushabu,Rathore, Rajendra
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supporting information
p. 2961 - 2968
(2016/03/12)
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- Synthesis, photophysical, electrochemical, and DSSC application of novel donor-acceptor triazole bridged dendrimers with a triphenylamine core and benzoheterazole as a surface unit
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Triazole bridged novel donor-acceptor dendrimers with triphenylamine as the core and benzoheterazole as the surface unit have been synthesized by click chemistry via a convergent approach. All the dendrimers exhibited excellent optical and electrochemical
- Rajavelu, Kannan,Rajakumar, Perumal,Sudip, Mandal,Kothandaraman, Ramanujam
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p. 10246 - 10258
(2016/12/07)
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- Improving organic memory performance through mounting conjugated branches on a triphenylamine core
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To study the influence of the number of branches mounted on molecular backbones on the thin-film morphology and performance of their memory devices, we successfully synthesized three conjugated small molecules containing triphenylamine and benzothiazole m
- Shi, Erbo,He, Jinghui,Zhuang, Hao,Liu, Hongzhang,Zheng, Yuanfang,Li, Hua,Xu, Qingfeng,Zheng, Junwei,Lu, Jianmei
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p. 2579 - 2586
(2016/07/14)
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- Bromine-substituted triphenylamine derivatives with improved hole-mobility for highly efficient green phosphorescent OLEDs with a low operating voltage
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Charge transport materials play a crucial role in organic light-emitting diodes (OLEDs) due to their effect on reducing the operating voltage and enhancing the power efficiency. To develop hole transport materials with improved hole-mobility, two novel br
- Du, Xiaoyang,Zhao, Juewen,Liu, Wei,Wang, Kai,Yuan, Shaolin,Zheng, Caijun,Lin, Hui,Tao, Silu,Zhang, Xiao-Hong
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p. 10301 - 10308
(2016/11/17)
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- Dual donor-π-acceptor type organic dyes for efficient dye-sensitized solar cells
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A series of novel triphenylamine (TPA)-based dyes that use double linkers between the electron donor and the electron acceptor are synthesized, characterized, and applied as photosensitizers for dye-sensitized solar cells. The dyes contain N-methylpyrrole (NMP) (MTPA-2 dye) and styrene (St) (STPA-2 dye), respectively, linkers on TPA. These linkers are expected to generate effective π-conjugation forming donor-π-acceptor (D-π-A) links. The photovoltaic performance of the dyes depends on the linker type. For the dual-St-π-linked dye, the charge transfer from the excited dye molecules to the conduction band of TiO2 is improved, making the efficiency of the corresponding devices higher than those of dye-based devices with NMP linkers and no linkers. The device with the dye bearing positions of C3 and C4 on NMP linkers has the lowest conjugation effect and efficiency. In particular, the STPA-2 dye shows a broad incident-photon-to-current conversion efficiency response with a signal of up to 700 nm, covering most of the ultraviolet-visible light region. Device efficiencies of 5.43% and 7.56% for dye-sensitized devices using the STPA-2 dye and the cis-RuL2(NCS)2 (N3) dye, respectively, were fabricated using the same method and measured under AM 1.5 irradiation.
- Chang, Pei-Yu,Wang, Po-Hsin,Lin, Wen-Churng,Yang, Chien-Hsin
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p. 9725 - 9738
(2016/11/11)
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- Synthesis and properties of the derivatives of triphenylamine and 1,8-naphthalimide with the olefinic linkages between chromophores
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Two donor-acceptor type molecules consisting of triphenylamine and 1,8-naphthalimide moieties with the olefinic linkages between chromophores were synthesized by Heck reaction. The compounds obtained are capable of forming molecular glasses with glass transition temperatures of 56 and 75 °C recorded for mono- and di-substituted derivatives of triphenylamine, respectively. They exhibit high thermal stabilities with 5% weight loss temperatures of 350 and 363 °C. Fluorescence quantum yields of the dilute solutions of the synthesized compounds range from 0.065 to 0.72 while those of the solid films are 0.028 and 0.034. The Stokes shifts increased with the increase of the solvent polarity. Cyclic voltammetry measurements revealed close values of the solid state ionization potentials (5.22 and 5.27 eV) and of electron affinities (-3.20 and -3.18 eV). For the layer of the monosubstituted derivative of triphenylamine core hole mobility was found to be 2.1 × 10-3 cm2 V-1 s-1. Good intrinsic hole transport parameters were theoretically estimated in the frame of Marcus theory, and the impact of polaron-type hole transport in these materials is discussed.
- Gudeika, Dalius,Sini, Gjergji,Jankauskas, Vygintas,Sych, Galyna,Grazulevicius, Juozas V.
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p. 2191 - 2201
(2016/01/20)
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- C-N cross-coupling reaction catalysed by reusable CuCr2O4 nanoparticles under ligand-free conditions: A highly efficient synthesis of triarylamines
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A convenient, efficient and ligand-free method for the C-N coupling reaction of anilines and aryl iodides was performed using CuCr2O4 nanoparticles. Copper chromite nanocatalyst improved the rate and facility of the synthesis of triarylamines. The heterogeneous catalyst was fully characterized by scanning electron microscopy, IR and X-ray diffraction techniques. Recyclability, excellent yields of products and short reaction times are the important advantages of this ligand-free procedure by using the CuCr2O4 nanoparticles. This journal is
- Safaei-Ghomi, Javad,Akbarzadeh, Zeinab,Khojastehbakht-Koopaei, Bahareh
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p. 28879 - 28884
(2015/04/14)
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- Sonochemically synthesis of arylethynyl linked triarylamines catalyzed by CuI nanoparticles: A rapid and green procedure for Sonogashira coupling
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A simple and green method was performed to the preparation of copper iodide nanoparticles by ultrasound approach. Consequently the synthesis of aryl ethynyl linked triarylamines was carried out through the Sonogashira coupling between iodo-substituted triarylamine and aryl acetylenes in the presence of CuI nanoparticles/Pd(PPh3)2Cl2 as an efficient catalytic system and triethylamine as the base under ultrasonic irradiation. Good to excellent yields of products and short reaction times are some of the important advantages of this solvent free protocol which were attained by both nano CuI and ultrasound conditions.
- Safaei-Ghomi, Javad,Akbarzadeh, Zeinab
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p. 365 - 370
(2014/11/08)
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- A convenient and efficient synthesis of triarylamine derivatives using CuI nanoparticles
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We report a simple and efficient method for the synthesis of triarylamine derivatives using copper iodide nanoparticles, 1,10-phenanthroline and potassium hydroxide. Copper iodide nanoparticles enhanced the rate and ease of reaction and exhibited a high influence in the efficient synthesis of various amine derivatives. The nanoparticles also increased the yields of products and decreased the reaction times in all cases. The heterogeneous mediator was fully characterized by scanning electron microscopy and X-ray diffraction techniques.
- Safaei-Ghomi, Javad,Akbarzadeh, Zeinab,Ziarati, Abolfazl
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p. 16385 - 16390
(2014/05/06)
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- TCNE-decorated triphenylamine-based conjugated polymer: Click synthesis and efficient turn-on fluorescent probing for Hg2+
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A type of triphenylamine-based conjugated polymer with cyano-containing chromophore in side chain, poly[(9,9-dioctyl)-2,7-fluorene-co-N-4-(1,1,4,4- tetracyanobuta-1,3-dienyl)-4,4′-triphenylamine] (P3) was successfully synthesized by catalyst-free and efficient click reaction between poly[(9,9-dioctyl)-2,7-fluorene-co-N-4-ethynyl-4,4′-triphenylamine] (P2) and tetracyanoethylene (TCNE). Chemical structures of intermediates and target polymer were verified by FT-IR and 1H NMR analyses. Fluorescence of P3's THF solution was specifically quenched by the introduction of I -, accompanied by the change of its apparent color from pale brown to light yellow. With the introduction of Hg2+, fluorescence of P3/I- complex recovered quickly and even exceeded the initial intensity of pristine P3 (when the concentration of Hg2+ above ~6.65 × 10-5 M). Other common cations brought very slight interference for P3/I- complex's response of Hg2+, and the detection limit of Hg2+ reached ~6.9 nM for such probing system.2013 Elsevier Ltd. All rights reserved.
- Shi, Wei,Ma, Fudong,Hui, Yonghai,Mi, Hongyu,Tian, Yong,Lei, Yanli,Xie, Zhengfeng
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- Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives
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The study of the chemical and electrochemical fluorescence switching properties of a family of substituted triphenylamine derivatives is reported. First of all, the synthesis of a family of six compounds is described. They are characterized by electrochemistry, UV-vis and fluorescence spectroscopy and spectroelectrochemistry. Theoretical calculations were performed in order to corroborate the experimental results. While these compounds emit blue to green light under UV irradiation with a large quantum yield (37%) in the case of one molecule, the fluorescence intensity is quenched upon oxidation. The fluorescence behavior can be switched between the strong fluorescent (neutral) state and the non-fluorescent (oxidized) state with a high contrast (around 1500 for the fluorescence intensity for one of these molecules). Furthermore, the chromatic contrast of three of these molecules reaches 70% that can be important for further applications. This journal is the Partner Organisations 2014.
- Quinton, Cassandre,Alain-Rizzo, Valerie,Dumas-Verdes, Cecile,Miomandre, Fabien,Clavier, Gilles,Audebert, Pierre
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p. 34332 - 34342
(2014/12/09)
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- New derivatives of triphenylamine and naphthalimide as ambipolar organic semiconductors: Experimental and theoretical approach
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Four new derivatives of triphenylamine containing different number of naphthalimide moieties were designed and synthesized by Suzuki condensation and their properties were studied by the experimental and theoretical tools. The compounds obtained are capable to form molecular glasses with glass transition temperatures ranging from 45 °C to 84°C. They exhibit very high thermal stabilities with 5% weight loss temperatures ranging from 429°C to 483°C. Fluorescence quantum yields of the dilute solutions in nonpolar solvents of the synthesized materials range from 0.63 to 0.78. Due to the pronounced electron donor-acceptor character, the compounds show dramatic solvatochromic red shifts of fluorescence (up to 250 nm) in polar solvents. The ionization potentials of the solid samples of the compounds established by electron photoemission spectrometry in air ranged from 5.57 to 6.01 eV. 4-(4′-(Di-(4″-methoxyphenyl)amino)phenyl)-N-(2-ethylhexyl)-1, 8-naphthalimide (5) was found to show ambipolar charge transport in air with the mobilities of charges exceeding 10-4 cm2 V-1 s-1 at high electric fields. The electron mobility of the compounds containing no methoxy groups were found to exceed the hole mobility by 2-3 orders of magnitude. The special role of methoxy groups in the ambipolar charge transport character of compound 5 is discussed in the frame of hopping Marcus theory, by applying a static theoretical analysis followed by a qualitative discussion of the positional disorder in some of these materials.
- Gudeika, Dalius,Grazulevicius, Juozas Vidas,Sini, Gjergji,Bucinskas, Audrius,Jankauskas, Vygintas,Miasojedovas, Arunas,Jursenas, Saulius
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- High performance aniline vapor detection based on multi-branched fluorescent triphenylamine-benzothiadiazole derivatives: Branch effect and aggregation control of the sensing performance
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A series of benzothiadiazole-pyridine branched triphenylamine derivatives TPA1BP, TPA2BP and TPA3BP have been designed and synthesized to sense aniline vapor with distinguished sensitivity, selectivity and repeatability via photoinduced electron transfer (PET). Suitable energy levels ensure the high selectivity to aniline for all three sensory materials. However, the aggregations of the three materials in the film state on a quartz substrate increase along with the branches, which highly deteriorate the sensing performance for less efficient fluorescence, lower contact area and inferior vapor penetration. The oriented ZnO nanorod array is introduced as the substrate to eliminate the aggregation and enhance the sensing performance, because of its high surface-to-volume ratio and 3D structure. Therefore, the cooperative effect that the sensing performance of TPAnBP increases with the number of branches could be observed; fluorescence intensities of the films on the nano-substrate are 34%, 45% and 54% quenched for TPA1BP, TPA2BP and TPA3BP, respectively, after exposure to 300 ppm aniline vapor for less than 5 s. Moreover, the fluorescences of all three sensory materials are almost 100% recovered by eluting with fresh air for 20 s and could be reused immediately. The detection limits are predicted to be 1 ppm for TPA1BP, 100 ppb for TPA2BP and 1 ppb for TPA3BP according to the fitted plot, demonstrating a significant cooperative effect of the molecular branches.
- Shi, Liqi,He, Chao,Zhu, Defeng,He, Qingguo,Li, Yang,Chen, Yan,Sun, Yuxi,Fu, Yanyan,Wen, Dan,Cao, Huimin,Cheng, Jiangong
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experimental part
p. 11629 - 11635
(2012/08/13)
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- Synthesis and applications of novel low bandgap star-burst molecules containing a triphenylamine core and dialkylated diketopyrrolopyrrole arms for organic photovoltaics
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In this study, we used facile synthetic routes to construct two well-defined starburst donor/acceptor conjugated small molecules with broad absorption features; in TPAKP-2 and TPAKP-3, triphenylamine (TPA) moieties served as electron donor core units and dialkylated diketopyrrolopyrrole (DKP) moieties with symmetrical thiophene units served as electron acceptors, in 1:2 and 1:3 ratios, respectively. Our investigation of the photophysical properties indicated that the absorption bands of TPAKP-2, and TPAKP-3 extended up to 793 nm, with low optical band gaps of 1.56 and 1.65 eV respectively. Under illumination with AM 1.5 white light (100 mW cm-2), we investigated the performance of bulk heterojunction (BHJ) photovoltaic devices incorporating an active layer of an electron-donor small molecule (TPAKP-2 or TPAKP-3) blended with an electron acceptor: [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) or [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) at various weight ratios. The photovoltaic device containing the donor TPAKP-3 and the acceptor PC71BM at a 1:3 weight ratio exhibited the best power conversion efficiency (1.81%), with an open circuit voltage of 0.66 V, a short circuit current density of 7.93 mA cm -2, and a fill factor of 34.7%.
- Sahu, Duryodhan,Tsai, Chia-Hua,Wei, Hung-Yu,Ho, Kuo-Chuan,Chang, Feng-Chih,Chu, Chih-Wei
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experimental part
p. 7945 - 7953
(2012/07/17)
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- Photoinduced processes of newly synthesized bisferrocene- and bisfullerene-substituted tetrads with a triphenylamine central block
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Photoinduced electron transfer processes of two newly synthesized tetrads with a triphenylamine (TPA) as central building block, to which bisfullerenes (C60) and bisferrocenes (Fc) are covalently connected, have been studied. One of them has a TPA linked with one C60 moiety and two ferrocene moieties C60-TPA-(Fc)2 and another tetrad has a TPA linked with two C60 moieties and one ferrocene unit (C60)2-TPA-Fc. The photophysical properties of (C60)m-TPA-(Fc)n have been investigated by applying the picosecond time-resolved fluorescence and nanosecond transient absorption techniques in both polar and nonpolar solvents. The charge separation process via the excited singlet state of the C60 moiety of the C60-TPA-(Fc)2 is more efficient than that of the (C60)2-TPA-Fc. It is found that the ratio of Fc-donor to C60-acceptor affects charge separation efficiency via the excited singlet state of the C60 moiety.
- Seok, Jai Han,Park, Seung Ho,El-Khouly, Mohamed E.,Araki, Yasuyuki,Ito, Osamu,Kay, Kwang-Yol
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experimental part
p. 1818 - 1825
(2009/08/15)
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- Triarylamine Derivative, Light-Emitting Substance, Light-Emitting Element, Light-Emitting Device, and Electronic Device
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A triarylamine derivative represented by a general formula (G1) given below is provided. Note that in the formula, Ar represents either a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; α represents a substituted or unsubstituted naphthyl group; β represents either hydrogen or a substituted or unsubstituted naphthyl group; n and m each independently represent 1 or 2; and R1 to R8 each independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
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- CARBAZOLE DERIVATIVE, AND LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE USING CARBAZOLE DERIVATIVE
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To provide a light-emitting element having high luminous efficiency and to provide a light-emitting device and an electronic device which consumes low power and is driven at low voltage, a carbazole derivative represented by the general formula (1) is provided. In the formula, α1, α2, α3, and α4 each represent an arylene group having less than or equal to 13 carbon atoms; Ar1 and Ar2 each represent an aryl group having less than or equal to 13 carbon atoms; R1 represents any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group; and R2represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group. In addition, l, m, and n are each independenly 0 or 1.
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- TRIARYLAMINE DERIVATIVE, LIGHT-EMITTING SUBSTANCE, LIGHT-EMITTING ELEMENT, LIGHT-EMITTING DEVICE, AND ELECTRONIC DEVICE
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A triarylamine derivative represented by a general formula (G1) given below is provided. Note that in the formula, Ar represents either a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; α represents a substituted or unsubstituted naphthyl group; β represents either hydrogen or a substituted or unsubstituted naphthyl group; n and m each independently represent 1 or 2; and R1 to R8 each independently represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, or a phenyl group.
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- AROMATIC TRIAMINE COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
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Disclosed is an aromatic triamine compound of specific structure having at least one terphenyl structure. Also disclosed is an organic electroluminescent device wherein an organic thin film composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode, and at least one layer in the organic thin film contains the aromatic triamine compound by itself or as a component of a mixture. Such an organic electroluminescent device has high luminous efficiency and long life, and the above-mentioned aromatic triamine compound enables to realize such an organic electroluminescent device.
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Page/Page column 74-77
(2008/06/13)
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- Aromatic triamine compound and organic electroluminescence device using the same
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Provided are an aromatic triamine compound of a specific structure having at least one terphenyl structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers having at least a luminescent layer is interposed between a cathode and an anode, wherein at least one layer of the above organic thin film layers contains the aromatic triamine compound described above in the form of a single component or a mixed component, and provided are the organic electroluminescence device having a high luminous efficiency and a long life and the novel aromatic triamine compound for materializing the same.
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- New luminescent compositions and their uses
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High quantum yield luminescent monomers, oligomers, and polymers, comprising benzotriazole repeating units and derivatives thereof have been discovered and utilized in optical devices and components therefor, including electroluminescent devices, light emitting devices, photoluminescent devices, organic light emitting diodes (OLEDs), OLED displays, sensors, and the like.
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- Paracyclophane molecules for two-photon absorption applications
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Chromophores having two-photon or other multi-photon absorptivity. The chromophores are based on a structure of four stilbenoid groups attached to a paracyclophane core, where each stilbenoid group comprises a nitrogen-containing organic group attached by
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Page/Page column 8-9
(2010/11/23)
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- Multi-armed chromophores with very large two-photon absorption cross-sections
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Provided are chromophores with very large two-photon absorption cross-sections. One group of these chromophores has the formula: (T—Q)n—N—Phm wherein Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-3 and m has a value of 3?n, and wherein T is wherein R1and R2are alkyl groups having 1 to 20 carbon atoms, provided that when Q is a single bond, the value of n is 2 or 3. Another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as defined above, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-4 and m has a value of 4?n, and wherein G is a 4-arm core unit. Yet another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as described previously, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-6 and m has a value of 6?n, and wherein G is a 6-arm core unit.
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- Cooperative Enhancement of Two-Photon Absorption in Multi-branched Structures
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Recent reports of molecular structures with considerably enhanced two-photon absorption cross-section have generated considerable interest in this phenomenon from both fundamental and applications perspectives. In this letter, we report cooperative enhanc
- Chung, Sung-Jae,Kim, Kyoung-Soo,Lin, Tzu-Chau,He, Guang S.,Swiatkiewicz, Jacek,Prasad, Paras N.
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p. 10741 - 10745
(2007/10/03)
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- Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. II. N-Phenylation of Diarylamines
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The condensations of 1,4-cyclohexanedione with several diphenylamines were investigated in order to determine the limit of the utility of this reaction for the N-phenylation of aromatic secondary amines. 4-Methoxy-, 4,4'-dimethyl-, and 4,4'-dibromodiphenylamines produced their N-phenylated compounds in fairly good yields, but 4-hydroxy-, 3-methoxy-, and 4,4'-bis(dimethylamino)diphenylamines produced poor yields.Nitro-substituted diphenylamines gave N-phenyl derivatives in low yields along with N-4-hydroxyphenyl derivatives.N,N'-Diphenyl-p-phenylenediamine and N,N'-diphenylbenzidine gave correspondig tetra-N-phenyl diamines in good yields.The condensation of N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-2-pyridylamine, phenothiazine, and carbazole with 1,4-cyclohexanedione were also examined.
- Haga, Kazuo,Iwaya, Katsumasa,Kaneko, Ryohei
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p. 803 - 808
(2007/10/02)
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