5-[4-(diphenylamino)phenyl]-thiophene-2-cyanoacrylic acid | 762269-56-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[4-(diphenylamino)phenyl]-thiophene-2-cyanoacrylic acid
• 英文别名: 2Cyano-3-[5-[4-(diphenylamino)phenyl]-2-thienyl]-propenoic acid；2-cyano-3-[5-[4-(N-phenylanilino)phenyl]thiophen-2-yl]prop-2-enoic acid
• CAS: 762269-56-7
• 化学式: C₂₆H₁₈N₂O₂S
• 分子量: 422.507
• InChiKey: KKQUCFHNVYLWDR-UHFFFAOYSA-N

物化性质

• 沸点：
  635.3±55.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 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：
  92.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[4-(diphenylamino)phenyl]-thiophene-2-cyanoacrylic acid 、 Mo(2,4,6-triisopropylbenzoate)₄ 以 甲苯 为溶剂， 反应 72.0h， 以45%的产率得到
  参考文献：
  名称：

  MM四重键由氰基丙烯酸酯配体支撑。将光子收集扩展到近红外和MLCT状态的研究†

  摘要：

  化合物反式-M 2（T我PB）2（大号）2和反式-M 2（T我PB）2（L' ）2已经从M之间的反应来制备2（T我PB）4（T我PB = 2,4,6-三异丙基苯甲酸酯，M = Mo或W）和LH或L'H（〜2当量），其中L = O 2 CC（CN）CH–C 6 H 4 –NPh 2并且L' = O 2 CC（CN）CH–C 4 H 3 S–C 6 H 4 –NPh 2。这些腈基丙烯酸酯的配体促进激烈中号2 δ到L或L'跨越范围550-1100纳米π* -transitions。两种钼配合物的特征在于单晶X射线研究，揭示了广泛的L–M 2 222–L或L'–M 2 222– L'M 2δ-配体π-共轭。通过使用密度泛函理论（DFT）和时变DFT的电子结构计算，循环伏安法，电子吸收和稳态发射光谱以及飞秒（fs）和纳秒（ns）的时间分辨瞬态吸收（TA），对新化合物进行了表征。 ）和fs时间分辨红外光谱（TRIR）。后者允许将S

  DOI：

  10.1039/c3sc50322d
• 作为产物：
  描述：

  5-(4-(二苯胺)苯基)噻吩-2-甲醛 在 ammonium acetate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 5-[4-(diphenylamino)phenyl]-thiophene-2-cyanoacrylic acid
  参考文献：
  名称：

  An iterative approach to the synthesis of thiophene-based organic dyes

  摘要：

  We developed an iterative synthetic method for oligo-aryl compounds using an organosilicon-based palladium-catalyzed cross-coupling reaction. Aryl compounds containing a benzyloxy(diisopropyl)silyl group (masked Si group) had sufficient chemical stability, and the unmasking step proceeded in a high yield under mild conditions. Both of the key unmasking/coupling steps required no strict anhydrous or degassed conditions. The developed procedure was used for the synthesis of thiophene-based organic dyes for dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.059

文献信息

• Rigid triarylamine-based efficient DSSC sensitizers with high molar extinction coefficients
  作者：Shengyun Cai、Xiaohao Hu、Zhiyun Zhang、Jianhua Su、Xin Li、Ashraful Islam、Liyuan Han、He Tian

  DOI：10.1039/c3ta01657a

  日期：——

  Five metal-free organic dyes (DIA1–DIA5) based on rigid triarylamine donors have been synthesized and their photophysical/electrochemical properties, theoretical calculations and dye-sensitized solar cell (DSSC) performances have been investigated. All the five dyes showed a high molar extinction coefficient (5.0 × 104–8.1 × 104 M−1 cm−1). Electrochemical measurement data indicates that the HOMO and LUMO energy levels can be conveniently tuned by alternating the π-spacer moiety. Among the five dyes, DIA3 showed the best photovoltaic performance, which was greatly increased to 8.09% by an optimized condition under standard global AM 1.5 solar light condition. The results show that the dyes based on this rigid donor are promising candidates for the improvement of the performance of DSSCs.

  合成了五种基于刚性三芳胺供体的无金属有机染料（DIA1–DIA5），并研究了它们的光物理/电化学性质、理论计算以及染料敏化太阳能电池（DSSC）的性能。所有五种染料均显示出高的摩尔消光系数（5.0 × 10^4–8.1 × 10^4 M−1 cm−1）。电化学测量数据显示，HOMO和LUMO能级可以通过改变π-间隔基团进行便捷调控。在这五种染料中，DIA3表现出最佳的光伏性能，在标准全球AM 1.5太阳光条件下，经过优化后其效率显著提高至8.09%。结果表明，基于这种刚性供体的染料是提升DSSC性能的有希望的候选材料。
• An iterative approach to the synthesis of thiophene-based organic dyes
  作者：Shinichiro Fuse、Hayato Yoshida、Takashi Takahashi

  DOI：10.1016/j.tetlet.2012.04.059

  日期：2012.6

  We developed an iterative synthetic method for oligo-aryl compounds using an organosilicon-based palladium-catalyzed cross-coupling reaction. Aryl compounds containing a benzyloxy(diisopropyl)silyl group (masked Si group) had sufficient chemical stability, and the unmasking step proceeded in a high yield under mild conditions. Both of the key unmasking/coupling steps required no strict anhydrous or degassed conditions. The developed procedure was used for the synthesis of thiophene-based organic dyes for dye-sensitized solar cells. (C) 2012 Elsevier Ltd. All rights reserved.
• MM quadruple bonds supported by cyanoacrylate ligands. Extending photon harvesting into the near infrared and studies of the MLCT states
  作者：Samantha E. Brown-Xu、Malcolm H. Chisholm、Christopher B. Durr、Sharlene A. Lewis、Vesal Naseri、Thomas F. Spilker

  DOI：10.1039/c3sc50322d

  日期：——

  The compounds trans-M2(TiPB)2(L)2 and trans-M2(TiPB)2(L′)2 have been prepared from the reactions between M2(TiPB)4 (TiPB = 2,4,6-triisopropylbenzoate, M = Mo or W) and LH or L′H (∼2 equiv.), respectively, where L = O2CC(CN)CH–C6H4–NPh2 and L′ = O2CC(CN)CH–C4H3S–C6H4–NPh2. These cyanoacrylate ligands promote intense M2δ to L or L′ π*-transitions that span the range 550–1100 nm. The two molybdenum complexes

  化合物反式-M 2（T我PB）2（大号）2和反式-M 2（T我PB）2（L' ）2已经从M之间的反应来制备2（T我PB）4（T我PB = 2,4,6-三异丙基苯甲酸酯，M = Mo或W）和LH或L'H（〜2当量），其中L = O 2 CC（CN）CH–C 6 H 4 –NPh 2并且L' = O 2 CC（CN）CH–C 4 H 3 S–C 6 H 4 –NPh 2。这些腈基丙烯酸酯的配体促进激烈中号2 δ到L或L'跨越范围550-1100纳米π* -transitions。两种钼配合物的特征在于单晶X射线研究，揭示了广泛的L–M 2 222–L或L'–M 2 222– L'M 2δ-配体π-共轭。通过使用密度泛函理论（DFT）和时变DFT的电子结构计算，循环伏安法，电子吸收和稳态发射光谱以及飞秒（fs）和纳秒（ns）的时间分辨瞬态吸收（TA），对新化合物进行了表征。 ）和fs时间分辨红外光谱（TRIR）。后者允许将S