- A simple AIE-based chemosensor for highly sensitive and selective detection of Hg2+and CN?
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A novel red-emitting chemosensor BCTT has been developed for the detection of Hg2+and CN?in DMF-water solution with high sensitivity and selectivity. It exhibited a ‘turn-on’ fluorescence upon binding with Hg2+based on its
- Li, Yiru,Zhou, Haitao,Chen, Wei,Sun, Guangchen,Sun, Lu,Su, Jianhua
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Read Online
- Platinum-based photosensitizer with near-infrared aggregation-induced emission for synergistic photodynamic-chemo theranostics
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Photodynamic therapy (PDT) is of great interest as an emerging paradigm towards cancer treatment, owing to its advantages of minimal invasiveness and low toxicity. In this work, we incorporated cisplatin into an AIE-based photosensitizer (BT) and achieved
- Gao, Yuting,Zhang, Jiaxin,He, Zhenyan,Luo, Liang,Yan, Chunjie
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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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supporting information
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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supporting information
p. 5512 - 5517
(2021/07/31)
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- Optical and electrochemical effects of triarylamine inclusion to alkoxy BODIPY-based derivatives
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Three new triphenylamine-BODIPY dyadsBDPT1-3have been designed and synthesized. Their optoelectronic properties were investigated, which revealed strong electronic interactions between the donor and acceptor moieties, together with high sensitivity to the inclusion of alkoxy groups. The properties of the dyads were compared with those of reference compoundsAandBDP1, which exhibit broader absorption in the visible region as a result of the inclusion of donor groups and extended conjugation of the BODIPY core. Fluorescence quenching was also observed, which was attributed to the photoinduced electron transfer, evidenced from solvatochromic measurements, quantum yields and theoretical calculations. The oxidation potentials of new compounds were found to be lower when compared with those of other BODIPY analogues with donor groups attached. The redox, computational, absorbance and emission data suggest that compoundsBDPT1-3exhibit promising properties for their application in organic photovoltaic or light emitting (optoelectronic) devices.
- Insuasty, Alberto,Madrid-Usuga, Duvalier,Mora-León, Ana G.,Ortiz, Alejandro,Rocha-Ortiz, Juan S.
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supporting information
p. 18114 - 18123
(2021/10/12)
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- Photo-Electroswitchable Arylaminoazobenzenes
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Azobenzenes appended with a redox-active arylamino group (redox auxiliary, RA) are prepared and shown to undergo fast, complete, and catalytic Z→E azo isomerization upon electron loss from the RA unit of the azobenzene. The RA-azo structures can be reversibly (E→Z→E)n cycled by sequential photo- and electrostimulation. Due to the robust nature of the RA?+-azo radical cation chain carrying species, initiation of electron transfer (ET) catalysis occurs at low levels (1.0-0.04 mol %) of catalytic loading and is effective even at Z-RA-azo concentrations of 10-4-10-5 M, yielding TONs (turnover numbers) of 100-2300 under such dilute conditions. The RA-azo Z→E conversion is demonstrated using chemical oxidation (redox switching), electrochemical oxidation (electro switching), and photochemical oxidation (photoredox switching). The Z→E acceleration is shown to be at least 2 × 109-fold for RA-azo 5. DFT calculations on methyl yellow suggest that a N-centered radical cation of the RA group stabilizes the Z→E N-N twist transition state of the RA?+-azo, yielding a large reduction in the barrier for RA?+-azo compared to neutral RA-azo. The RA-azo structure class has nanomechanical features that can be toggled with photo- and electrostimulation, the latter offering a quick switch for complete Z→E conversion.
- Saint-Louis, Carl Jacky,Warner, David J.,Keane, Katie S.,Kelley, Melody D.,Meyers, Connor M.,Blackstock, Silas C.
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p. 11341 - 11353
(2021/08/24)
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- Monocarbazole/dicarbazole hole transport material as well as preparation method and application thereof
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The invention discloses a monocarbazole/dicarbazole hole transport material as well as a preparation method and application thereof. The chemical structural general formula of the monocarbazole/dicarbazole hole transport material is shown as a formula I.
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Paragraph 0068; 0072-0074
(2020/11/23)
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- One-pot synthesis of a white-light emissive bichromophore operated by aggregation-induced dual emission (AIDE) and partial energy transfer
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Merocyanine-triarylamine bichromophores are readily synthesized by sequentially Pd-catalyzed insertion-alkynylation-Michael-Suzuki four-component reactions. White-light emissive systems form upon aggregation in 1 : 99 and 0.1 : 99.9 vol percent CH2Cl2-cyclohexane mixtures, ascribed to aggregation-induced dual emission (AIDE) in combination with partial energy transfer between both chromophore units as supported by spectroscopic studies.
- Biesen, Lukas,Deni?en, Melanie,Hannen, Ricarda,Hoffmann, Katrin,Itskalov, Dana,Müller, Thomas J. J.,Nirmalananthan-Budau, Nithiya,Reiss, Guido J.,Resch-Genger, Ute
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supporting information
p. 7407 - 7410
(2020/07/15)
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- Hole transport material based on tetraarylbutadiene, preparation method and applications thereof
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The invention discloses a hole transport material based on tetraarylbutadiene, wherein the hole transport material has a chemical general formula represented by a formula (I), and is an organic smallmolecule using tetraphenyl butadiene, tetrathiophene butadiene or tetrafuran butadiene as a core and using alkoxy or alkylthio substituted diphenylamine, triphenylamine, carbazole, phenothiazine or phenoxazine as a side group. According to the invention, the preparation method of the hole transport material has characteristics of simple synthesis and low cost, and has the potential of large-scaleproduction; and the hole transport material has good photoelectric property and good thermal stability, can be used as a hole transport material to be applied to photoelectric devices such as organicphotoconductive drums, OLED display devices, solar cells and the like, and has great application prospects.
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Paragraph 0119; 0121-0124
(2020/02/29)
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- Long-Lived Local Triplet Excited State and Charge Transfer State of 4,4′-Dimethoxy Triphenylamine-BODIPY Compact Electron Donor/Acceptor Dyads
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The spin-orbit charge transfer intersystem crossing (SOCT-ISC) and the formation of a long-lived charge transfer (CT) state were studied with a series of 4,4′-dimethoxy triphenylamine-BODIPY compact electron donor/acceptor dyads. Different torsion freedom
- Hou, Yuqi,Liu, Jinling,Zhang, Nan,Zhao, Jianzhang
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p. 9360 - 9374
(2020/12/01)
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- Red or near-infrared light operating negative photochromism of a binaphthyl-bridged imidazole dimer
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The development of red or near-infrared light (NIR) switchable photochromic molecules is required for an efficient utilization of sunlight and regulation of biological activities. While the photosensitization of photochromic molecules to red or NIR light has been achieved by a two-photon absorption process, the development of a molecule itself having sensitivity to red or NIR light has been now a challenging study. Herein, we developed an efficient molecular design for realizing red or NIR-light-responsive negative photochromism based on binaphthyl-bridged imidazole dimers. The introduction of electron-donating substituents shows the red shift of the absorption band at the visible-light region because of the contribution of a charge-transfer transition. Especially, the introduction of a di(4-methoxyphenyl)amino group (TPAOMe) and a perylenyl group largely shifts the absorption edge of the stable colored form to 900 nm. In addition, because the absorption band of one of the derivatives substituted with TPAOMe covers the whole visible-light region, the colored form shows a neutral gray color. Upon red (660 nm) or NIR-light (790 nm) irradiation, we observed the negative photochromic reaction from the stable colored form to the metastable colorless form. Therefore, the substituted binaphthyl-bridged imidazole dimers constitute the attractive photoswitches within a biological window.
- Kometani, Aya,Inagaki, Yuki,Mutoh, Katsuya,Abe, Jiro
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p. 7995 - 8005
(2020/05/27)
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- Luminescence Tunable Europium and Samarium Complexes: Reversible On/Off Switching and White-Light Emission
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Single-molecule functional materials with luminescence tunable by external stimuli are of increasing interest due to their application in sensors, display devices, biomarkers, and switches. Herein, new europium and samarium complexes with ligands having triphenylamine (TPA) groups as the redox center and 2,2′-bipyridine (bpy) as the coordinating groups and diketonate (tta) as the second ligand have been constructed. The complexes show white-light emission in selected solvents for proper mixtures of the emission from Ln3+ ions and the ligands. Meanwhile, they exhibit reversible luminescence switching on/off properties by controlling the external potential owing to intramolecular energy transfer from the Ln3+ ions to the electrochemically generated radical cation of TPA+. Time-dependent density functional theory (TD-DFT) calculations have been performed to study the electronic spectra. The proposed intramolecular energy transfer processes have been verified by density functional theory (DFT) studies.
- Chen, Jing,Xie, Ziyu,Meng, Lingyi,Hu, Ziying,Kuang, Xiaofei,Xie, Yiming,Lu, Can-Zhong
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supporting information
p. 6963 - 6977
(2020/05/18)
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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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Paragraph 0095-0096
(2019/12/25)
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- Anthracene structure-based cavity transport material as well as preparation method and application thereof
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The invention discloses an anthracene structure-based cavity transport material as well as a preparation method and the application thereof. The cavity transport material is a novel organic micromolecular cavity transport material taking anthracene as a c
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Paragraph 0092; 0093; 0094
(2018/08/03)
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- Perovskite hole transport material based on triptycene mother nucleus and preparation method thereof
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The present invention discloses a perovskite hole transport material based on a triptycene mother nucleus and a preparation method thereof. The material is 2,6,14-tri(50-(N,N-bi(4-methoxyphenyl)aminophenol-4-yl)-3,4-ethylenedioxythiophene-2-yl)-triptycene. The preparation method has the advantages of mild synthesis conditions, simple steps, cheap and easily obtained synthetic raw materials, and low synthesis costs. The prepared material has a good thermal stability, solubility and film forming property. An ultraviolet-visible light absorption spectrum indicates the hole transport material based on the triptycene mother nucleus has a large conjugate structure, has a more suitable HOMO level (-5.08 eV) than that of a mainstream hole transport material Spiro-MeOTAD, and provides a strong driving force for hole transporting. The carrier mobility of the material measured by a space charge limiting current method is 8x10cm.Vs. The perovskite hole transport material has potential.
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Paragraph 0061; 0062; 0065; 0066
(2018/11/03)
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- A highly fluorescent water soluble spirobifluorene dye with a large Stokes shift: Synthesis, characterization and bio-applications
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The first water-soluble spirobifluorene derivative has been synthesized, which exhibits high fluorescence quantum yield and a large Stokes shift (>100 nm). Proteins induce changes in the emission color, allowing to reach the nanomolar detection limit. Cellular uptake and cytotoxicity studies in living cells revealed its biocompatibility, indicating potential application for live cell imaging.
- Schlüter, Friederike,Riehemann, Kristina,Kehr, Nermin Seda,Quici, Silvio,Daniliuc, Constantin G.,Rizzo, Fabio
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supporting information
p. 642 - 645
(2018/02/06)
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- Dithieno[3,2-b:2′,3′-d] pyrrole-based hole transport materials for perovskite solar cells with efficiencies over 18%
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Dithieno[3,2-b:2′,3′-d]pyrrole (DTP) derivatives are one of the most important organic photovoltaic materials due to better π-conjugation across fused thiophene rings. In this work, two new hole transport materials (HTMs), H16 and H18, have been obtained through a facile synthetic route by cross linking triarylamine-based donor groups with a 4-(4-methoxyphenyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole (MPDTP) and N-(4-(4H-dithieno[3,2 b:2′,3′-d]pyrrol-4-yl)phenyl)-4-methoxy-N-(4-methoxyphenyl)aniline (TPDTP) unit, respectively. The H16 HTM outperforms the H18 in terms of conductivity, hole mobility, and hole transport at the interface. This result could be attributed to the enhancement of the conductivity, hole mobility and high quality of the film exerted by the MPDTP core. The optimized device based on H16 exhibits a high power conversion efficiency (PCE) of 18.16%, which is comparable to that obtained with the state-of-the-art-HTM spiro-OMeTAD (18.27%). Furthermore, the long-term aging test shows that the H16 based device has good stability after two months of aging under controlled (20%) humidity in the dark. Importantly, the synthesis cost of H16 is roughly 1/5 of that of spiro-OMeTAD. The present finding highlights the potential of DTP based HTMs for efficient PSCs.
- Mabrouk, Sally,Zhang, Mengmeng,Wang, Zhihui,Liang, Mao,Bahrami, Behzad,Wu, Yungen,Wu, Jinhua,Qiao, Qiquan,Yang, Shangfeng
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supporting information
p. 7950 - 7958
(2018/05/14)
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- Electron Transfer around a Molecular Corner
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The distance dependence of electron transfer (ET) is commonly investigated in linear rigid rod-like compounds, but studies of molecular wires with integrated corners imposing 90° angles are very rare. By using spirobifluorene as a key bridging element and by substituting it at different positions, two isomeric series of donor-bridge-acceptor compounds with either nearly linear or angled geometries were obtained. Photoinduced ET in both series is dominated by rapid through-bond hole hopping across oligofluorene bridges over distances of up to 70 ?. Despite considerable conformational flexibility, direct through-space and through-solvent ET is negligible even in the angled series. The independence of the ET rate constant on the total number of fluorene units in the angled series is attributed to a rate-limiting tunneling step through the spirobifluorene corner. This finding is relevant for multidimensional ET systems and grids in which individual molecular wires are interlinked at 90° angles.
- Schmidt, Hauke C.,Larsen, Christopher B.,Wenger, Oliver S.
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supporting information
p. 6696 - 6700
(2018/03/26)
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- Donor and acceptor substituted triphenylamines exhibiting bipolar charge-transporting and NLO properties
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Donor-acceptor type triphenylamine-based malonodinitriles were synthesized and their thermal, optical, photophysical, electrochemical and nonlinear optical properties were studied. The synthesized compounds formed glasses with the glass transition temperatures ranging from 38 to 107 °C. The ionization potentials of the samples of the compounds established by cyclic voltammetry were found to be in the range of 5.50–5.57 eV, while those estimated by photoelectron emission spectrometry ranged from 5.36 to 5.74 eV. The electron affinity values of the compounds were found to be in the range of ?3.41–?3.05 eV. The ambipolar charge-transporting properties were observed for the layers of triphenylamine-based malonodinitriles. Hole mobilities of the layers of the compounds were in the range of 10?7–10?6 cm2/V·s, while electron mobilities were by ca. two orders of magnitude higher. All the synthesized compounds had positive sign for second order hyperpolarizability.
- Gudeika, Dalius,Bundulis, Arturs,Mihailovs, Igors,Volyniuk, Dmytro,Rutkis, Martins,Grazulevicius, Juozas V.
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p. 431 - 440
(2017/02/10)
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- Synthesis of Triarylamines via Sequential C-N Bond Formation
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A one-pot domino N-arylation protocol is described using diaryliodonium reagents under copper catalysis. The reaction uses both aryl groups of the diaryliodonium reagent to generate triarylamines starting from simple anilines, representing an atom-economical preparation of an important class of organic material building blocks.
- Modha, Sachin G.,Popescu, Mihai V.,Greaney, Michael F.
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p. 11933 - 11938
(2017/11/24)
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- Containing 1, 1 - double-(4 - aminophenyl) cyclohexane group of the hole transporting material and its preparation method and application (by machine translation)
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The invention discloses a containing 1, 1 - double-(4 - aminophenyl) cyclohexane group of the hole transporting material and its preparation method and application, which belongs to the perovskite technical field of solar cell. Formula 1 illustrated structure: wherein: R=type 2 or type 3 or type 4 or type 5 or type 6 or type 7 or type 8 or type 9 or type 10. The invention also disclosed the above-mentioned hole transporting material preparation method and its application. Hole transporting material of the present invention, it is easy to prepare and refining, and has higher yield; it has good solubility, easily soluble in common organic solvent; has higher HOMO energy level, the energy of the can and the perovskite material very good match; has higher hole mobility; has a relatively high glass transition temperature and thermal stability, easy to form very good amorphous film. (by machine translation)
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Paragraph 0112; 0113; 0114; 0115
(2017/08/28)
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- PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
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Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.
- Tao, Xiaochun,Li, Lei,Zhou, Yu,Qian, Xuanying,Zhao, Min,Cai, Liangzhen,Xie, Xiaomin
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supporting information
p. 1749 - 1754
(2017/10/06)
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- Electron Accumulation on Naphthalene Diimide Photosensitized by [Ru(2,2′-Bipyridine)3]2+
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In a molecular triad comprised of a central naphthalene diimide (NDI) unit flanked by two [Ru(bpy)3]2+ (bpy = 2,2′-bipyridine) sensitizers, NDI2- is formed after irradiation with visible light in deaerated CH3CN
- Skaisgirski, Michael,Guo, Xingwei,Wenger, Oliver S.
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supporting information
p. 2432 - 2439
(2017/03/16)
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- General design of self-doped small molecules as efficient hole extraction materials for polymer solar cells
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The development of high performance hole transport materials (HTMs) without a chemical dopant is critical to achieve long-term device durability. The general design of self-doping materials based on a phenolamine structure with strong electronic spin conc
- Xue, Yuyuan,Guo, Peipei,Yip, Hin-Lap,Li, Yuan,Cao, Yong
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supporting information
p. 3780 - 3785
(2017/03/08)
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- Photoinduced electron transfer in a triarylamine-organoboron-Ru(2,2′-bipyridine)32+ compound
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Long-range electron transfer reactions play a key role in biological photosynthesis, and they are likely to play an important role for future artificial photosynthetic endeavors as well. The possibility to control the rates for long-range electron transfer with external stimuli is of particular interest in this context. In the work presented herein, we explored a donor–bridge–acceptor compound in which intramolecular electron transfer from a triarylamine donor to a photoexcited Ru(bpy)32+ (bpy?=?2,2′-bipyridine) acceptor occurs across an organoboron bridge over a distance of approximately 22??. Fluoride has a high binding affinity to the organoboron bridge in apolar solutions, and the resulting organofluoroborate has a significantly different electronic structure. We explored to what extent the change from an electron-deficient organoboron wire to an electron-rich organofluoroborate bridge affects long-range electron transfer between the distant triarylamine donor and the Ru(bpy)32+ acceptor.
- Heinz, Luisa G.,Wenger, Oliver S.
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p. 230 - 236
(2017/03/07)
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- Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes
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A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.
- Topchiy, Maxim A.,Dzhevakov, Pavel B.,Rubina, Margarita S.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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supporting information
p. 1908 - 1914
(2016/04/20)
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- For organic electronic device, modified stable electrode having a work function and method
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A device including an electrode, the electrode having a surface; a molecule bound to the surface of the electrode through a binding group; an organic electronic material in electrical contact with the electrode, wherein the molecule comprises at least one fluorinated aryl group, wherein the electrode contains a transparent conductive metal oxide, a carbon nanotube, or graphene.
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Paragraph 0063
(2017/01/05)
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- The effect of different alkyl chains on the photovoltaic performance of D-π-A porphyrin-sensitized solar cells
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In this study, a series of novel D-π-A porphyrin sensitizers with different alkyl chains were designed and synthesized for dye-sensitized solar cells. The effects of different alkyl chains (methyl, methoxyl and hexyloxy groups) on the photophysical, electrochemical and photovoltaic performance were investigated systematically. The results indicate that the molar extinction coefficients of three dyes normally increase as the alkyl chain length increases. Furthermore, it is also found that the incident photo-to-current conversion efficiencies (IPCEs), short circuit current (Jsc) and open circuit voltage (Voc) of the dye-sensitized solar cells (DSSCs) based on WH-C1, YD20 and WH-C2 increase with the elongation of alkyl chains in the order of WH-C1 sc of 13.10 mA cm-2, a Voc of 831.10 mV, and a fill factor (FF) of 0.70.
- Chen, Jiangzhao,Ko, Songguk,Liu, Linfeng,Sheng, Yusong,Han, Hongwei,Li, Xiong
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p. 3736 - 3746
(2015/05/20)
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- Triazatruxene-Based Hole Transporting Materials for Highly Efficient Perovskite Solar Cells
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Four center symmetrical star-shaped hole transporting materials (HTMs) comprising planar triazatruxene core and electron-rich methoxy-engineered side arms have been synthesized and successfully employed in (FAPbI3)0.85(MAPbBr3)0.15 perovskite solar cells. These HTMs are obtained from relatively cheap starting materials by adopting facile preparation procedure, without using expensive and complicated purification techniques. Developed compounds have suitable highest occupied molecular orbitals (HOMO) with respect to the valence band level of the perovskite, and time-resolved photoluminescence indicates that hole injection from the valence band of perovskite into the HOMO of triazatruxene-based HTMs is relatively more efficient as compared to that of well-studied spiro-OMeTAD. Remarkable power conversion efficiency over 18% was achieved using 5,10,15-trihexyl-3,8,13-tris(4-methoxyphenyl)-10,15-dihydro-5H-diindolo[3,2-a:3′,2′-c]carbazole (KR131) with compositive perovskite absorber. This result demonstrates triazatruxene-based compounds as a new class of HTM for the fabrication of highly efficient perovskite solar cells.
- Rakstys, Kasparas,Abate, Antonio,Dar, M. Ibrahim,Gao, Peng,Jankauskas, Vygintas,Jacopin, Gwénolé,Kamarauskas, Egidijus,Kazim, Samrana,Ahmad, Shahzada,Gr?tzel, Michael,Nazeeruddin, Mohammad Khaja
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supporting information
p. 16172 - 16178
(2016/01/15)
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- Synthesis and redox properties of mono-, di- and tri-metallic platinum-ethynyl complexes based on the trans-Pt(C6H4N{C6H4OCH3-4}2)(CCR)(PPh3)2 motif
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The Pt-halide complex trans-PtI{C6H4NAr2}(PPh3)2 (Ar = C6H4OMe-4, 3) was prepared by oxidative addition of N(C6H4I)Ar2 (2) to Pt(PPh3)
- Vincent, Kevin B.,Parthey, Matthias,Yufit, Dmitry S.,Kaupp, Martin,Low, Paul J.
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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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- Synthesis and performance of new quinoxaline-based dyes for dye sensitized solar cell
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New quinoxaline-based dyes were synthesized and applied as a sensitizer for dye-sensitized solar cell. A quinoxaline moiety was used as an electron withdrawing group and triphenylamine and phenothiazine derivatives were introduced as electron donating gro
- Jung, Chang Young,Song, Cheol Jun,Yao, Wang,Park, Jong Min,Hyun, In Ho,Seong, Dong Hoon,Jaung, Jae Yun
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p. 204 - 210
(2015/06/16)
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- Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow
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An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.
- Hernandez-Perez, Augusto C.,Caron, Antoine,Collins, Shawn K.
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supporting information
p. 16673 - 16678
(2015/11/09)
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- Tetramethoxybenzene is a good building block for molecular wires: Insights from photoinduced electron transfer
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Two donor bridge-acceptor molecules with terminal triarylamine and Ru(bpy)32+ (bpy = 2,2′-bipyridine) redox partners were synthesized and investigated by cyclic voltammetry, optical absorption, luminescence, and transient absorption spectroscopy. The two dyads differ only by the central bridging unit, which was tetramethoxybenzene (tmb) in one case and unsubstituted phenylene (ph) in the other case. Photoirradiation of the Ru(bpy)32+ complex of the two dyads triggers intramolecular electron transfer from the triarylamine to the 3MLCT-excited metal complex, and this process occurs with time constants of 1.5 and 6.8 ns for the tmb- and ph-bridged dyads, respectively. Thermal electron transfer in the reverse direction then leads to disappearance of the photoproduct with a time constant of 10 ns in both dyads. The faster rate of photoinduced charge transfer in the tmb-bridged dyad can be understood in the framework of a hole-tunneling model in which the electron-rich tmb bridge imposes a more shallow barrier than the less electron-rich ph spacer. Until now tmb-based molecular wires have received very little attention, and alkoxy substituents have been mostly used for improving the solubility of oligo-p-phenylene vinylene (OPV) and oligo-p-phenylene ethynylene (OPE) wires. Our study illustrates how four alkoxy-substituents on a phenylene backbone can have a significant influence on the charge-transfer properties of a molecular wire, and this is relevant in the greater context of a future molecular electronics technology.
- Heinz, Luisa G.,Yushchenko, Oleksandr,Neuburger, Markus,Vauthey, Eric,Wenger, Oliver S.
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p. 5676 - 5684
(2015/06/16)
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- Fluoride binding to an organoboron wire controls photoinduced electron transfer
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We demonstrate that the rates for long-range electron transfer can be controlled actively by tight anion binding to a rigid rod-like molecular bridge. Electron transfer from a triarylamine donor to a photoexcited Ru(bpy)32+ acceptor (bpy = 2,2′-bipyridine) across a 2,5-diboryl-1,4-phenylene bridge occurs within less than 10 ns in CH2Cl2 at 22 °C. Fluoride anions bind with high affinity to the organoboron bridge due to strong Lewis base/Lewis acid interactions, and this alters the electronic structure of the bridge drastically. Consequently, a large tunneling barrier is imposed on photoinduced electron transfer from the triarylamine to the Ru(bpy)32+ complex and hence this process occurs more than two orders of magnitude more slowly, despite the fact that its driving force is essentially unaffected by fluoride addition. Electron transfer rates in proteins could potentially be regulated via a similar fundamental principle, because interactions between charged amino acid side chains and counter-ions can modulate electronic couplings between distant redox partners. In artificial donor-bridge-acceptor compounds, external stimuli have been employed frequently to control electron transfer rates, but the approach of exploiting strong Lewis acid/Lewis base interactions to regulate the tunneling barrier height imposed by a rigid rod-like molecular bridge is conceptually novel and broadly applicable, because it is largely independent of the donor and the acceptor, and because the effect is not based on a change of the driving-force for electron transfer. The principle demonstrated here can potentially be used to switch between conducting and insulating states of molecular wires between electrodes. This journal is
- Chen, Jing,Wenger, Oliver S.
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p. 3582 - 3592
(2015/05/27)
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- Synthesis of a new class of triphenylamine-containing poly(ether-imide)s for electrochromic applications
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A novel triphenylamine (TPA)-containing bis(ether anhydride) monomer, namely 4,4′-bis(3,4-dicarboxyphenoxy)triphenylamine dianhydride, was synthesized and reacted with various aromatic diamines leading to a series of new poly(ether-imide)s (PEI). Most of these PEIs were soluble in organic solvents and could be easily solution cast into flexible and strong films. The polymer films exhibited good thermal stability with glass-transition temperatures in the range 211-299°C. The polymer films exhibited reversible electrochemical processes and stable color changes (from transparent to navy blue) with high coloration efficiency and contrast ratio upon electro-oxidation. During the electrochemical oxidation process, a crosslinked polymer structure was developed due to the coupling reaction between the TPA radical cation moieties in the polymer chains. These polymers can be used to fabricate electrochromic devices with high coloration efficiency, high redox stability, and fast response time.
- Hsiao, Sheng-Huei,Chang, Pei-Chi,Wang, Hui-Min,Kung, Yu-Ruei,Lee, Tzong-Ming
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p. 825 - 838
(2014/03/21)
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- Lability-controlled syntheses of heterometallic clusters
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A bulky bidentate ligand was used to stabilize a macrocyclic [Fe III8CoII6] cluster. Tuning the basicity of the ligand by derivatization with one or two methoxy groups led to the isolation of a homologous [FeIII8CoII 6] species and a [FeIII6FeII 2CoIII2CoII2] complex, respectively. Lowering the reaction temperatures allowed isolation of [Fe III6FeII2CoIII 2CoII2] clusters with all three ligands. Temperature-dependent absorption data and corresponding experiments with iron/nickel systems indicated that the iron/cobalt self-assembly process was directed by the occurrence of solution-state electron-transfer-coupled spin transition (ETCST) and its influence on reaction intermediate lability. Spin offs: A bulky bidentate ligand stabilizes a [Fe8Co6] cluster. Changing the ligand's electronic state by derivatization with one or two methoxy groups gave a homologous [Fe8Co6] species and a [Fe8Co4] complex, respectively. Reactions at low temperature allowed the isolation of the [Fe8Co4] cluster with all three ligands through a solution-state electron-transfer-coupled spin transition (ETCST) which acts as a self-assembly directing process.
- Newton, Graham N.,Mitsumoto, Kiyotaka,Wei, Rong-Jia,Iijima, Fumichika,Shiga, Takuya,Nishikawa, Hiroyuki,Oshio, Hiroki
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supporting information
p. 2941 - 2944
(2014/04/03)
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- Nickel-catalyzed triarylamine synthesis: Synthetic and mechanistic aspects
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An improved protocol was described for the amination of chloroarenes with diarylamines under NiCl2(PCy3)2 catalysis in the presence of a Grignard reagent as base. This method fully suits bromo-/iodoarene substrates as well, and even is expanded to certain aryl tosylates. A preliminary investigation into the mechanism suggests that this amination reaction might proceed through NiI and NiIII intermediates rather than via the usually expected Ni0-Ni II cycle.
- Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
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supporting information
p. 1232 - 1236
(2014/03/21)
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- GREEN ZINC PORPHYRIN SENSITIZERS AND THEIR APPLICATIONS
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The present invention relates to zinc porphyrin-based photosensitive dyes, specifically to zinc porphyrin-based photosensitive dyes with green transparency. The photosensitive dyes exhibit high push-pull ability in the zinc porphyrin-based structure, high
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Paragraph 0164-0165
(2013/04/13)
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- D-A-π-A organic sensitizers containing a benzothiazole moiety as an additional acceptor for use in solar cells
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Three novel triphenylamine-based D-A-π-A-featured dyes (Z1-Z3) have been designed, synthesized and characterized for use in dye-sensitized solar cells. Benzothiazole was incorporated as an additional acceptor, which greatly enhanced the molar extinction c
- Zeng, Juan,Zhang, Tenglong,Zang, Xufeng,Kuang, Daibin,Meier, Herbert,Cao, Derong
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p. 505 - 513
(2013/07/19)
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- Synthesis and electrochromic properties of aromatic polyetherimides based on a triphenylamine-dietheramine monomer
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A series of electroactive polyetherimides (PEIs) with triphenylamine (TPA) units were prepared from the polycondensation reactions of 4,4′-bis(p- aminophenoxy)triphenylamine with aromatic tetracarboxylic dianhydrides via a conventional two-step technique.
- Hsiao, Sheng-Huei,Wang, Hui-Min,Chang, Pei-Chi,Kung, Yu-Ruei,Lee, Tzong-Ming
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p. 2925 - 2938
(2013/07/27)
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- Molecular design of D-π-A Type II organic sensitizers for dye sensitized solar cells
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Four new type II organic dyes with D-π-A structure (donor-π- conjugated-acceptor) and two typical type II sensitizers based on catechol as reference dyes are synthesized and applied in dye sensitized solar cells (DSCs). The four dyes can be adsorbed on TiO2 through hydroxyl group directly. Electron injection can occur not only through the anchoring group (hydroxyl group) but also through the electron-withdrawing group (i£CN) located close to the semiconductor surface. Experimental results show that the type II sensitizers with a D-π-A system obviously outperform the typical type II sensitizers providing much higher conversion efficiency due to the strong electronic push-pull effect. Among these dyes, LS223 gives the best solar energy conversion efficiency of 3.6%, with Jsc=7.3 mA·cm-2, Voc=0.69 V, FF=0.71, the maximum IPCE value reaches 74.9%. Copyright
- Li, Shifeng,Yang, Xichuan,Qu, Dingfeng,Wang, Weihan,Wang, Yu,Sun, Licheng
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p. 2315 - 2321,7
(2020/09/16)
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- A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction
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The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.
- Islam,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir
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experimental part
p. 1352 - 1357
(2011/10/12)
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- Light-emitting dyes derived from bifunctional chromophores of diarylamine and oxadiazole: Synthesis, crystal structure, photophysics and electroluminescence
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The synthesis, structural, photophysical, electrochemical and electroluminescent properties of a novel class of bifunctional molecule are reported in which the hole-transporting triarylamine and electron-transporting oxadiazole components were combined. The strongly luminescent compounds displayed good thermal and morphological stability as well as intense fluorescence both in solution and thin film at room temperature. The effects of the introduction of substituents with different electronic properties upon their absorption and emissive characteristics were correlated with theoretical calculations using density functional theory computations. The photophysics and electrochemistry of such systems were compared to those for the corresponding molecule without an oxadiazole ring. The bipolar compounds could be vacuum-sublimed and applied as emissive dopants for the fabrication of electrofluorescent, organic light-emitting devices with relatively simpler device structures, which can emit tunable colors by varying the aryl ring substituents.
- He, Ze,Kan, Chi-Wai,Ho, Cheuk-Lam,Wong, Wai-Yeung,Chui, Chung-Hin,Tong, Ka-Lap,So, Shu-Kong,Lee, Tik-Ho,Leung, Louis M.,Lin, Zhenyang
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experimental part
p. 333 - 343
(2011/06/21)
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- ELECTRONIC DEVICES COMPRISING NOVEL PHOSPHONIC ACID SURFACE MODIFIERS
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In some embodiments, the inventions described herein relate to a composition of matter comprising a molecule having the structure: wherein: independently at each occurrence, R1 is a halogen, a alkyl group, a heteroalkyl group, an aryl group, or a heteroaryl group; R2 comprises from 3 to 30 CH2- groups, n = 0-5, m = 0-5, q = 1-3, and R2 comprises at least one ether linkage
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Page/Page column 28
(2010/11/03)
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- Molecular engineering of organic sensitizers for dye-sensitized solar cell applications
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Novel unsymmetrical organic sensitizers comprising donor, electron-conducting, and anchoring groups were engineered at a molecular level and synthesized for sensitization of mesoscopic titanium dioxide injection solar cells. The unsymmetrical organic sens
- Hagberg, Daniel P.,Yum, Jun-Ho,Lee, HyoJoong,De Angelis, Filippo,Marinado, Tannia,Karlsson, Karl Martin,Humphry-Baker, Robin,Sun, Licheng,Hagfeldt, Anders,Graetzel, Michael,Nazeeruddin
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p. 6259 - 6266
(2008/12/20)
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- Enhanced poling efficiency in highly thermal and photostable nonlinear optical chromophores
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A series of nonlinear optical chromophores based on the highly thermal and photostable tricyanovinylidenediphenylaminobenzene (TCVDPA) was synthesized and their thermal and optical properties were investigated. Modification of the TCVDPA chromophore with
- Faccini, Mirko,Balakrishnan, Muralidharan,Diemeer, Mart B. J.,Hu, Zhi-Peng,Clays, Koen,Asselberghs, Inge,Leinse, Arne,Driessen, Alfred,Reinhoudt, David N.,Verboom, Willem
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scheme or table
p. 2141 - 2149
(2009/10/15)
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- A new hybrid phosphine ligand for palladium-catalyzed amination of aryl halides
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A new hybrid phosphine was designed. The phosphine combines two common structural characteristics found among the effective phosphine ligands reported recently, namely, three tert-alkyl substituents binding to the phosphorus and an aryl group at an appropriate position. A hybrid phospine/palladium system is versatile and effective for the coupling reaction of various aryl halides with primary and secondary amines including carbazole.
- Suzuki, Ken,Hori, Yoji,Kobayashi, Tohru
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supporting information; experimental part
p. 652 - 656
(2009/05/07)
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- Promising core structure for nuclear receptor ligands: Design and synthesis of novel estrogen receptor ligands based on diphenylamine skeleton
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Novel diphenylamine-type estrogen receptor ligands were designed and synthesized, and their biological activities were evaluated by means of binding assays for estrogen receptor-α and -β and cell proliferation assay using MCF-7 cells. Compounds 4f, 11b, 12c, and 8 showed moderate estrogenic activities. We propose that the diphenylamine skeleton may be a privileged structure for various nuclear receptor ligands, including RAR, RXR, and AR ligands.
- Ohta, Kiminori,Chiba, Yuki,Ogawa, Takumi,Endo, Yasuyuki
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scheme or table
p. 5050 - 5053
(2009/05/26)
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- Process for the preparation of arylamines
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The present invention provides a process for the preparation of arylamines comprises reacting aryl halide and aryl amine/heterocyclic amine. The said process is carried out in the presence of a solvent, catalyst and a base.
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Page/Page column 8-9
(2008/06/13)
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