5-(4’-(diphenylamino)-[1,1’-biphenyl]-4-yl)thiophene-2-carbaldehyde | 1172120-67-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(4’-(diphenylamino)-[1,1’-biphenyl]-4-yl)thiophene-2-carbaldehyde
• 英文别名: 5-(4'-(diphenylamino)biphenyl-4-yl)thiophene-2-carbaldehyde；5-(4-(diphenylamino)biphenylyl)thiophene-2-carbaldehyde；5-(diphenylaminobiphenylene)thiophene-2-carbaldehyde；5-[4-[4-(N-phenylanilino)phenyl]phenyl]thiophene-2-carbaldehyde
• CAS: 1172120-67-0
• 化学式: C₂₉H₂₁NOS
• 分子量: 431.558
• InChiKey: UEACXXYNNSGTRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• 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-(4’-(diphenylamino)-[1,1’-biphenyl]-4-yl)thiophene-2-carbaldehyde 、 氰乙酸 在 ammonium acetate 、 溶剂黄146 作用下， 反应 12.0h， 以61%的产率得到(E)-2-cyano-3-(5'-(4''-(diphenylamino)biphenylyl)thiophen-2'-yl)acrylic acid
  参考文献：
  名称：

  利用含有三亚芳基共轭物的有机双染料的染料敏化太阳能电池

  摘要：

  通过便捷的方法合成了一系列包含给体（D），桥（B）和受体（A）的有机偶极化合物，形成了一种D–B–A型二元体，并成功地用于染料敏化太阳能电池。中心桥由三个线性连接的亚芳基基团，即亚苯基或噻吩基制成。供体基团是芳族胺，即二苯胺或萘基苯胺基团。受体基团是氰基丙烯酸，可以固定在TiO 2的表面上在光伏设备中。这些设备表现出色，典型的量子效率为5–7％，最佳入射光子到电流的转换效率（IPCE）超过80％。用萘基苯胺供体基团制得的装置的性能略好于用二苯胺供体基团制得的装置。含有亚苯基-噻吩基-亚苯基桥基的化合物的性能要优于具有其他三芳基键合的化合物。使用具有B3LYP功能的时变密度泛函理论（TDDFT）模型分析了它们的光化学行为。

  DOI：

  10.1016/j.tet.2009.04.024
• 作为产物：
  描述：

  4-硼酸三苯胺 在 四(三苯基膦)钯 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 47.0h， 生成 5-(4’-(diphenylamino)-[1,1’-biphenyl]-4-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D–π–A dyes

  摘要：

  New metal-free organic sensitizers containing a benzo[d]thiazole or phenyl unit as the pi-conjugated system, a triphenylamine as an electron donor, and a cyanoacrylic acid moiety as an electron acceptor were synthesized and used for dye-sensitized solar cells. Photophysical and electrochemical properties of these dyes were investigated, and their performances as sensitizers in solar cells were measured. The introduction of a benzo[d]thiazole unit into the molecular structure resulted in a high incident photon-to-current conversion efficiency (more than 70%) from 340 nm to 600 nm. One solar cell containing a benzo[d]thiazole unit, produced a eta of 5.85% (J(SC) = 10.63 mA cm(-2), V-OC = 0.72 V, and ff = 0.77) under 100 mW cm(-2) simulated AM 1.5 G solar irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.004

文献信息

• DYE COMPOUND AND DYE-SENSITIZED SOLAR CELL
  申请人：Chow Tahsin J.

  公开号：US20100076205A1

  公开（公告）日：2010-03-25

  A dye compound is described, which is expressed by formula (I): wherein A 1 , A 2 and A 3 each independently represent a substituted or unsubstituted 1,4-phenylene or 2,5-thiophene group, and B 1 and B 2 each independently represent a substituted or unsubstituted aryl group. The dye compound is suitably used as a dye sensitizer in a dye sensitized solar cell (DSSC).

  描述了一种染料化合物，其化学式为（I）：其中A1、A2和A3分别独立表示取代或未取代的1,4-苯基或2,5-噻吩基团，B1和B2分别独立表示取代或未取代的芳基团。该染料化合物适合用作染料敏化太阳能电池（DSSC）中的染料敏化剂。
• Triaryl linked donor acceptor dyads for high-performance dye-sensitized solar cells
  作者：Yuan Jay Chang、Tahsin J. Chow

  DOI：10.1016/j.tet.2009.09.036

  日期：2009.11

  The effect of changing substituents of organic dyes for their performance on dye-sensitized solar cells (DSSCs) is examined. These dyes consist of an aromatic amine donor group, a cyanoacrylic acid acceptor group, and a triaryl spacer group, while they are linked together by consecutive palladium catalyzed coupling reactions. These materials exhibit strong charge transfer absorption bands in the UV/vis

  研究了改变有机染料取代基对其染料敏化太阳能电池（DSSC）的性能的影响。这些染料由芳族胺供体基团，氰基丙烯酸受体基团和三芳基间隔基团组成，它们通过连续的钯催化的偶联反应连接在一起。这些材料在UV / vis区域显示出很强的电荷转移吸收带。通过循环伏安法估算了它们的氧化还原电势水平，发现它们非常适合DSSC中的电荷流。在芳族胺的苯基上添加给电子取代基会增加施主基团上的电子密度，从而降低HOMO / LUMO带隙。这些染料被化学吸附在纳米晶TiO 2的表面上，并通过标准操作将其制作成DSSC。对于典型的设备，最大的单色入射光子-电流转换效率（IPCE）可以达到80％，短路光电流密度（J sc）为16.34 mA cm -2，开路光电压（V oc） 0.68 V，填充因数（FF）0.55，对应于6.05％的总转换效率。
• US8183393B2
  申请人：——

  公开号：US8183393B2

  公开（公告）日：2012-05-22
• Dye-sensitized solar cell utilizing organic dyads containing triarylene conjugates
  作者：Yuan Jay Chang、Tahsin J. Chow

  DOI：10.1016/j.tet.2009.04.024

  日期：2009.6

  A series of organic dipolar compounds containing a donor (D), a bridge (B), and an acceptor (A), forming a D–B–A type of dyads, were synthesized by convenient methods and were utilized successfully on dye-sensitized solar cells. The central bridges were made of three linearly connected arylene groups, i.e., phenylenes or thiophenylenes. The donor groups were aromatic amines, i.e., either a diphenylamine

  通过便捷的方法合成了一系列包含给体（D），桥（B）和受体（A）的有机偶极化合物，形成了一种D–B–A型二元体，并成功地用于染料敏化太阳能电池。中心桥由三个线性连接的亚芳基基团，即亚苯基或噻吩基制成。供体基团是芳族胺，即二苯胺或萘基苯胺基团。受体基团是氰基丙烯酸，可以固定在TiO 2的表面上在光伏设备中。这些设备表现出色，典型的量子效率为5–7％，最佳入射光子到电流的转换效率（IPCE）超过80％。用萘基苯胺供体基团制得的装置的性能略好于用二苯胺供体基团制得的装置。含有亚苯基-噻吩基-亚苯基桥基的化合物的性能要优于具有其他三芳基键合的化合物。使用具有B3LYP功能的时变密度泛函理论（TDDFT）模型分析了它们的光化学行为。
• Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D–π–A dyes
  作者：Zhenhua Ci、Xiaoqiang Yu、Ming Bao、Chaolei Wang、Tingli Ma

  DOI：10.1016/j.dyepig.2012.11.004

  日期：2013.3

  New metal-free organic sensitizers containing a benzo[d]thiazole or phenyl unit as the pi-conjugated system, a triphenylamine as an electron donor, and a cyanoacrylic acid moiety as an electron acceptor were synthesized and used for dye-sensitized solar cells. Photophysical and electrochemical properties of these dyes were investigated, and their performances as sensitizers in solar cells were measured. The introduction of a benzo[d]thiazole unit into the molecular structure resulted in a high incident photon-to-current conversion efficiency (more than 70%) from 340 nm to 600 nm. One solar cell containing a benzo[d]thiazole unit, produced a eta of 5.85% (J(SC) = 10.63 mA cm(-2), V-OC = 0.72 V, and ff = 0.77) under 100 mW cm(-2) simulated AM 1.5 G solar irradiation. (C) 2012 Elsevier Ltd. All rights reserved.