5-[2-(4-diphenylamino-phenyl)-vinyl]-thiophene-2-carbaldehyde | 945230-80-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[2-(4-diphenylamino-phenyl)-vinyl]-thiophene-2-carbaldehyde
• 英文别名: 5-[(E)-2-[4-(N-phenylanilino)phenyl]ethenyl]thiophene-2-carbaldehyde
• CAS: 945230-80-8
• 化学式: C₂₅H₁₉NOS
• 分子量: 381.498
• InChiKey: DMAZOKMXTJNWJX-DTQAZKPQSA-N

物化性质

• 沸点：
  572.9±50.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[2-(4-diphenylamino-phenyl)-vinyl]-thiophene-2-carbaldehyde 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 50.5h， 生成 4-[(E)-2-[5-[(E)-2-[5-[tert-butyl(dihydroxy)silyl]thiophen-2-yl]ethenyl]thiophen-2-yl]ethenyl]-N,N-diphenylaniline
  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 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 32.0h， 生成 5-[2-(4-diphenylamino-phenyl)-vinyl]-thiophene-2-carbaldehyde
  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

• Tuning the HOMO and LUMO Energy Levels of Organic Chromophores for Dye Sensitized Solar Cells
  作者：Daniel P. Hagberg、Tannia Marinado、Karl Martin Karlsson、Kazuteru Nonomura、Peng Qin、Gerrit Boschloo、Tore Brinck、Anders Hagfeldt、Licheng Sun

  DOI：10.1021/jo701592x

  日期：2007.12.1

  approach optimal energy level composition in the TiO2−dye−iodide/triiodide system in the dye-sensitized solar cells. HOMO and LUMO energy level tuning is achieved by varying the conjugation between the triphenylamine donor and the cyanoacetic acid acceptor. This is supported by spectral and electrochemical experiments and TDDFT calculations. These results show that energetic tuning of the chromophores

  为了接近染料敏化太阳能电池中TiO 2-染料-碘化物/三碘化物系统中的最佳能级组成，已经合成了一系列有机发色团。HOMO和LUMO能级调节是通过改变三苯胺供体与氰基乙酸受体之间的共轭来实现的。光谱和电化学实验以及TDDFT计算支持了这一点。这些结果表明，发色团的能量调节是成功的，并且满足了染料敏化太阳能电池的热力学标准，观察到电损耗取决于发色团的大小和方向。
• 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。
• Assessment of new gem-silanediols as suitable sensitizers for dye-sensitized solar cells
  作者：Gabriella Barozzino Consiglio、Fabio Pedna、Cosimo Fornaciari、Fabrizia Fabrizi de Biani、Gabriele Marotta、Paolo Salvatori、Riccardo Basosi、Filippo De Angelis、Alessandro Mordini、Maria Laura Parisi、Maurizio Peruzzini、Gianna Reginato、Maurizio Taddei、Lorenzo Zani

  DOI：10.1016/j.jorganchem.2012.10.012

  日期：2013.1

  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.