- Crystal structure of p-formylphenyl, di(p-methylphenyl)amine, and p-bromophenyl, di(o-bromo-p-methylphenyl)amine
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p-Formylphenyl, di(p-methylphenyl)amine (1), and p-bromophenyl, di(o-bromo-p-methylphenyl)amine (2) were prepared and characterized by X-ray crystallography. Formyl-substituted triphenylamine(1) crystallizes in the monoclinic space group P21/c with a = 9.068(1), b = 17.115(2), c = 11.297(2) A, β = 106.73(1)°, V = 1679.0(5) A3 and Z =4. Bromo -substituted compound 2 crystallizes in the monoclinic space group P21/n with a = 16.170(4), b = 7.9477(8), c = 16.906(4) A, β = 117.67(2)°, V = 1924.1(7) A3 and Z = 4. The N atoms deviate slightly from the plane of the bonded C atoms and the benzene ring planes are rotated by 25-67° to avoid overlap of the ortho-substituted atoms. The major force of crystal formation comes from the multiple phenyl embraces (MPE).
- Xue, Minzhao,Liu, Yangang,Huang, Deyin,Gong, Bin
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- Structural, spectral, electrochemistry, thermal properties and theoretical studies on 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone
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The title compound 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone (C28H24ClN3O, Mr= 453.96) was synthesized by the reaction of 4-[N, N-di(4-tolyl)amino] benzaldehyde with 2-chlorobenzohydrazide, and its structure was characterized by IR, 1H NMR, 13H NMR, high-resolution mass spectrometry and single-crystal X-ray diffraction. The crystal belongs to Monoclinic, space group P2(1)/n with a = 12.626(3), b = 12.609(3), c = 15.837(3) ?, β = 90.00(3)°, Z = 5, V = 2512.5(9) ?3, Mr= 453.95, Dc = 1.280 g/cm3, μ = 0.183 mm-1, F(0 0 0) = 1024, R = 0.0432 and wR = 0.1087. X-ray analysis revealed that one of the benzene ring and acylhydrazone were essentially planar, the 2-chloro benzene ring and amide were non-planar, the torsion angles C(1)C(6)C(7)O(1) and C(5)C(6)C(7)O(1) are 61.4(5)° and -114.4(4)°. The thermal stability studies indicate that the title compound is stable up to 341.1 °C. The spectral, electrochemistry properties and theoretical studies show that the title compound is a good candidate for the charge-transporting materials.
- Lizeng, Liu,Wei, Li,Xianfang, Meng,Dongzhi, Liu,Gongfeng, Xu,Zhengchen, Bai
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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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- Direct Olefination of Fluorinated Quinoxalines via Cross- Dehydrogenative Coupling Reactions: A New Near-Infrared Probe for Mitochondria
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A large library of 5,8-distyrylquinoxaline fluorophores was synthesized in good-to-excellent yields via a palladium-catalyzed oxidative C–H/C–H cross-coupling of electron-deficient fluorinated quinoxalines with electron-rich styrenes. The resulting quinoxaline fluorophores (Qu-Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm?1 in dichloromethane. The bioimaging performance of the Qu-Fluors was shown to have potential as near-infrared fluorescent probes for mitochondria. (Figure presented.).
- Zhang, Zeyuan,Zheng, Yiwen,Sun, Zuobang,Dai, Zhen,Tang, Ziqiang,Ma, Jiangshan,Ma, Chen
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supporting information
p. 2259 - 2268
(2017/07/07)
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- Efficient delayed fluorescence via triplet-triplet annihilation for deep-blue electroluminescence
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Four 2-(styryl)triphenylene derivatives (TSs) were synthesized for deep-blue dopant materials. By using a pyrene-containing compound, DMPPP, as the host, the TS-doped devices exhibited significant delayed fluorescence via triplet-triplet annihilation, providing the highest quantum efficiency of 10.2% and a current efficiency of 12.3 cd A-1. the Partner Organisations 2014.
- Chou,Chou,Chen,Su,Liao,Lin,Lin,Yen,Chen,Cheng
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p. 6869 - 6871
(2014/06/23)
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- Tuning the photophysical, thermal properties and electronic energy levels in the triphenylamine derivatives by benzoylhydrazone architecture
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A novel of triphenylamine derivatives with more extended π-conjugated systems achieved by benzoylhydrazone architecture were synthesized under mild condition with high yields. The dependence of their photophysical, electrochemistry and thermal properties on their chemical structure is discussed. Compared with the N,N-di(4-methylphenyl)aniline, the thermostability of the five triphenylamine-based hydrozones is dramatically promoted. These compounds are stable up to 345 °C according to thermogravimetric analysis. The energy levels of the four compounds were finely tuned by introducing the electron-donating and -withdrawing groups to the triphenylamine core which are supported by the fluorescence spectra and transit fluorescence spectra of the compounds (-H > -CH3 > -Cl > Pyridine > -NO2). Their multiple cyclic voltammetry study and density functional study suggest these materials to be promising hole-transport properties.
- Liu, Lizeng,Meng, Xianfang,Li, Wei,Zhou, Xueqin,Bai, Zhengchen,Liu, Dongzhi,Lv, Yunrong,Li, Rui-Hong
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- Electrochromic properties of novel chalcones containing triphenylamine moiety
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A series of novel electrochromic chalcones containing triphenylamine units were synthesized by Aldol reaction and characterized by NMR, IR and MS. Their optical, electrochemical properties were investigated using UV-vis, photoluminescence spectra and cyclic voltammetry. The molecular orbital energy levels and excitation energies were calculated by quantum chemical calculation. It was found that the fluorescence intensity is decreasing with formation of charge-transfer state. The existence of electron donating group on triphenylamine unites caused a significant bathochromic shift of the UV absorption maximum and increased EHOMO and ELUMO. The electrochromic property of the synthesized compounds was studied by spectroelectrochemical experiments. The results showed that the chalcones containing triphenylamine moiety presented good electrochromic stability, with a color change from yellow to blue as applied potentials ranging from 0.0 to 2.8 V. The coloring and bleaching time was in the range of 2.9-4.2 s and 1.7-3.3 s, respectively.
- Jin, Huiyi,Li, Xianggao,Tan, Tingfeng,Wang, Shirong,Xiao, Yin,Tian, Jianhua
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p. 154 - 160
(2014/04/17)
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- APPLICATION OF TRIPHENYLENE DERIVATIVES IN ORGANIC ELECTROLUMINESCENT DEVICES
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Triphenylene derivatives having a structure of formula (1) are provided. Ar represents an aromatic compound, n is 1 to 3, and each of R and R1 to R13 is a member independently selected from the group consisting of hydrogen, halo, cyano, trifluoromethyl, amino, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C1-C20 heterocycloalkyl, C1-C20 heterocycloalkenyl, aryl and heteroaryl. The compound of the present invention may function as a host emitter or dopant in the emitter layer of OLED device. An OLED device is also herein provided.
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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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p. 333 - 343
(2011/06/21)
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- Polyaromatic amines. Part 3: Synthesis of poly(diarylamino)styrenes and related compounds
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The title compounds were synthesised and characterised as part of a study into new aromatic amines for charge transporting materials. Compounds 12-16, 20-24 and 27-34 are alkene linked triarylamines, compounds 35-36 are hydrazone derivatives and compounds 38-41 are pyrrole substituted triarylamines. Each compound was characterised by cyclic voltammetry.
- Plater, M. John,Jackson, Toby
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p. 4673 - 4685
(2007/10/03)
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- Bis(aminostyryl)benzene compounds and synthetic intermediates thereof, and process for preparing the compounds and intermediates
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To provide compounds, which are suitable for use as an organic luminescent material capable of developing intense luminescence which is yellow to red, and a process for preparing in general and high efficiency. A bis(aminostyryl)benzene compound of the following general formula [I] is provided wherein R2and R3independently represent an unsubstituted aryl group, and R1and R4independently represent an aryl group, and R5to R8, independently represent a cyano group or the like. A process for the preparation thereof is described wherein a 4-(N,N-diarylamino)benzaldehyde and a diphosphonic acid ester or diphosphonium are subjected to condensation reaction. Intermediates of the bis(aminostyryl)benzene compound are also described.
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