(E)-N,N-diphenyl-4-(2-(thiophen-2-yl)vinyl)aniline | 1042977-81-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-N,N-diphenyl-4-(2-(thiophen-2-yl)vinyl)aniline
• 英文别名: (E)-2-[2-(4-diphenylaminophenyl)vinyl]thiophene；2-[2-(4-diphenylamino-phenyl)-vinyl]-thiophene；N,N-diphenyl-4-[(E)-2-thiophen-2-ylethenyl]aniline
• CAS: 1042977-81-0
• 化学式: C₂₄H₁₉NS
• 分子量: 353.488
• InChiKey: IVJKXSVYTNGPLM-OBGWFSINSA-N

物化性质

• 沸点：
  515.8±29.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N,N-diphenyl-4-(2-(thiophen-2-yl)vinyl)aniline 在 正丁基锂 、 potassium tert-butylate 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 49.0h， 生成 N,N-diphenyl-4-[(E)-2-[5-[(E)-2-thiophen-2-ylethenyl]thiophen-2-yl]ethenyl]aniline
  参考文献：
  名称：

  Assessment of new gem-silanediols as suitable sensitizers for dye-sensitized solar cells

  摘要：

  Four novel gem-silanediol-containing organic dyes featuring a highly conjugated backbone have been synthesized in order to investigate their potential as active materials for photovoltaics. After spectroscopic characterization, the compounds showing the best light harvesting and electrochemical properties were applied as sensitizers in dye-sensitized solar cells (DSSCs). Interestingly, photovoltaic cells built using the new silanediol dyes showed low power conversion efficiencies (eta), comparable to those obtained with silicon-based sensitizers having simple azobenzene moieties as the light-harvesting units. Such values are mostly due to unsatisfactory photocurrent densities; a computational study suggested that the latter can be justified considering the insufficient degree of charge transfer taking place during photoexcitation of the silicon-containing sensitizers, which is likely to make electron injection into the TiO2 layer less efficient. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.012
• 作为产物：
  描述：

  N,N-diphenyl-4-(2-thiophen-2-ylethenyl)aniline 在 碘 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以61%的产率得到(E)-N,N-diphenyl-4-(2-(thiophen-2-yl)vinyl)aniline
  参考文献：
  名称：

  Assessment of new gem-silanediols as suitable sensitizers for dye-sensitized solar cells

  摘要：

  Four novel gem-silanediol-containing organic dyes featuring a highly conjugated backbone have been synthesized in order to investigate their potential as active materials for photovoltaics. After spectroscopic characterization, the compounds showing the best light harvesting and electrochemical properties were applied as sensitizers in dye-sensitized solar cells (DSSCs). Interestingly, photovoltaic cells built using the new silanediol dyes showed low power conversion efficiencies (eta), comparable to those obtained with silicon-based sensitizers having simple azobenzene moieties as the light-harvesting units. Such values are mostly due to unsatisfactory photocurrent densities; a computational study suggested that the latter can be justified considering the insufficient degree of charge transfer taking place during photoexcitation of the silicon-containing sensitizers, which is likely to make electron injection into the TiO2 layer less efficient. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.012

文献信息

• Tunable two-photon absorption near-infrared materials containing different electron-donors and a π-bridge center with applications in bioimaging in live cells
  作者：Ming Kong、Ting Wang、Xiaohe Tian、Fang Wang、Yanqiu Liu、Qiong Zhang、Hui Wang、Hongping Zhou、Jieying Wu、Yupeng Tian

  DOI：10.1039/c5tc00716j

  日期：——

  The 2PA can be adjusted by the electron donating group and π-bridge center among the dyes.

  2PA可以通过染料中的电子给予基团和π-桥中心进行调整。
• Trivalent Boron as an Acceptor in Donor–π–Acceptor-Type Compounds for Single- and Two-Photon Excited Fluorescence
  作者：Zhi-qiang Liu、Qi Fang、Dong Wang、Du-xia Cao、Gang Xue、Wen-tao Yu、Hong Lei

  DOI：10.1002/chem.200304833

  日期：2003.10.17

  The synthesis, structure, and fluorescence properties of a series of new donor-pi-acceptor (D-pi-A) type compounds, with a trivalent boron, protected by two mesityl groups, as acceptor, and with various typical donors and different pi-conjugated bridges, are reported. All these stable organoboron compounds show intense single-photon excited fluorescence (SPEF) and two-photon excited fluorescence (TPEF)

  一系列新的供体-pi-受体（D-pi-A）型化合物的合成，结构和荧光性质，三价硼由两个均三基团保护，作为受体，并带有各种典型的供体和不同的pi报道了共轭桥。所有这些稳定的有机硼化合物在从蓝色到绿色的宽光谱范围内均显示出强烈的单光子激发荧光（SPEF）和双光子激发荧光（TPEF），SPEF的光谱峰位置与TPEF。在两种化合物的X射线晶体结构中显示出非常强的Cbond; B（mesityl）（2）键和良好共轭的pi系统，表明基态的某些电荷转移特征。同时，光谱数据表明，在激发态下，从供体到受体的电荷转移大大增强。根据典型的结构数据和全面的光谱数据，可以得出以下结构性质关系：1）中度芳基氨基供体比强烷基氨基供体能更有效地增强SPEF和TPEF强度；2）二苯乙烯具有比苯乙烯基噻吩更好的pi桥，因为它具有增强和蓝移相应D-pi-A化合物的SPEF和TPEF的能力；和3）与无硼前体和其他类似物相比，-B
• The design of nonlinear optical chromophores exhibiting large electro-optic activity and high thermal stability: The role of donor groups
  作者：Fenggang Liu、Hongyan Xiao、Yuhui Yang、Haoran Wang、Hua Zhang、Jialei Liu、Shuhui Bo、Zhen Zhen、Xinhou Liu、Ling Qiu

  DOI：10.1016/j.dyepig.2016.03.003

  日期：2016.7

  of tetrahydroquinolinyl chromophore is 65% and 110% larger than that of either the diethylaminophenyl or triarylaminophenyl chromophores, respectively. The doped film containing the tetrahydroquinolinyl chromophore showed an r33 value of 126 pm/V at the concentration of 25 wt% which is much higher than the electro-optic activity of the diethylaminophenyl derived chromophore (39 pm/V) and six times

  合成了一种基于N-（4-二丁基氨基苯基）四氢喹啉基供体的新型生色团，与基于二乙氨基苯基或三芳基氨基苯基供体的传统生色团进行比较。循环伏安法测量表明，新发色团的能隙比结构上相关的发色团小得多。密度泛函理论计算表明，四氢喹啉基生色团的分子二次超极化率（μβ）值分别比二乙基氨基苯基或三芳基氨基苯基生色团的大65％和110％。包含四氢喹啉基生色团的掺杂膜的r 33浓度为25 wt％时的126 pm / V值，远高于二乙氨基苯基衍生的发色团（39 pm / V）的电光活性，是传统三芳基氨基苯基发色团（19 pm / V）的六倍）。四氢喹啉基生色团具有比通常使用的烷基生色团更高的热稳定性（其起始分解温度高于280°C）。
• A novel organic chromophore for dye-sensitized nanostructured solar cells
  作者：Daniel P. Hagberg、Tomas Edvinsson、Tannia Marinado、Gerrit Boschloo、Anders Hagfeldt、Licheng Sun

  DOI：10.1039/b603002e

  日期：——

  A novel and efficient polyene-diphenylaniline dye for dye-sensitized solar cells has been synthesized. The dye has a short synthesis route and is readily adsorbed on TiO2 under a variety of dye-bath conditions. The overall solar-to-energy conversion efficiency is over 5% in the preliminary tests, in comparison with the conventional N719 dye which gives 6% under the same conditions. The dye is designed for future use also in solid state devices, with triarylamine based hole conductors.

  一种新型高效的聚烯-二苯基苯胺染料已成功合成，可用于染料敏化太阳能电池。该染料合成路线短，在各种染料浴条件下易于吸附在TiO2上。在初步测试中，其太阳能到电能的总转换效率超过5%，而传统染料N719在相同条件下只能达到6%。该染料还可用于固态器件，与基于三芳基胺的空穴导体配合使用。
• Highly Efficient, Thermally and Chemically Stable Second Order Nonlinear Optical Chromophores Containing a 2-Phenyl-tetracyanobutadienyl Acceptor
  作者：Xiaoming Wu、Jianyao Wu、Yunqi Liu、Alex K-Y. Jen

  DOI：10.1021/ja983537+

  日期：1999.1.1