(2E,2'E)-3,3'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(2-(5-formylthiophen-2-yl)acrylonitrile) | 1427737-35-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E,2'E)-3,3'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(2-(5-formylthiophen-2-yl)acrylonitrile)
• 英文别名: (2E,2'E)-3,3'-((hexylazanediyl)bis(4,1-phenylene))bis(2-(5-formylthiophen-2-yl)acrylonitrile)
• CAS: 1427737-35-6
• 化学式: C₃₄H₂₉N₃O₂S₂
• 分子量: 575.755
• InChiKey: QCICDTSCZWZRDK-MKYUKRCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.96
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-3,3'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(2-(5-formylthiophen-2-yl)acrylonitrile) 、 氰乙酸 在 哌啶 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以32%的产率得到(2E,2'E)-3,3'-(5,5'-(1E,1'E)-2,2'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(1-cyanoethene-2,1-diyl)bis(thiophene-5,2-diyl))bis(2-cyanoacrylic acid)
  参考文献：
  名称：

  Synthesis of bianchored metal free organic dyes for dye sensitized solar cells

  摘要：

  Two bianchored metal free organic dyes (Car-th-CN and Dpa-th-CN) were designed and synthesized for DSSC application, in which carbazole or diphenylamine moieties were used as the donor, cyano vinyl thiophene unit as the pi-bridge and cyanoacrylic acid group as the electron acceptor. The structures of the synthesized dyes were confirmed by NMR, HR-Mass and elemental analysis. The optical, electrochemical, theoretical and photovoltaic properties of the synthesized dyes were investigated. Fabricated photovoltaic devices based on carbazole unit as a donor (Car-th-CN) showed a maximum current conversion efficiency of 4.04% under AM 1.5 illumination (85 mW cm(-2)) and monochromatic incident photon to current efficiency (IPCE) of 38.1%. The reason for the higher efficiency of Car-th-CN is due to the planar nature of carbazole moiety and hence increases the capability of adsorbed dye amount and electron lifetime in TiO2 surface. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.01.014
• 作为产物：
  描述：

  二苯胺 在 potassium tert-butylate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 (2E,2'E)-3,3'-(4,4'-(hexylazanediyl)bis(4,1-phenylene))bis(2-(5-formylthiophen-2-yl)acrylonitrile)
  参考文献：
  名称：

  Bi-anchoring organic sensitizers of type D-(π-A) 2 comprising thiophene-2-acetonitrile as π-spacer and malonic acid as electron acceptor for dye sensitized solar cell applications

  摘要：

  Two new bi-anchoring organic sensitizers of type D-(pi-A)(2) comprising the identical pi-spacer (thiophene-2-acetonitrile) and electron acceptor (malonic acid) but different aryl amine as electron donors (diphenylamine and carbazole) were synthesized, characterized and fabricated metal free dye-sensitized solar cell devices. The intra molecular charge transfer property and electrochemical property of these dyes were investigated by molecular absorption, emission, cyclic voltammetric experiments and in addition, quantum chemical calculation studies were performed to provide sufficient driving force for the electron injection into the conduction band of TiO2 which leads to efficient charge collection. Among the fabricated devices, carbazole based device exhibits high current conversion efficiency (eta = 4.7%) with a short circuit current density (J(SC)) 15.3 mA/cm(2), an open circuit photo voltage (V-OC) of 0.59 V and a fill factor of 0.44 under AM 1.5 illumination (85 mW/cm(2)) compared to diphenylamine based device. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2015.03.032