3-{6-[3,4,5-tris(dodecyloxy)phenyl]dithieno[3,2-b:2',3'-a]thien-2-yl}-2-cyanoacrylic acid | 1422273-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-{6-[3,4,5-tris(dodecyloxy)phenyl]dithieno[3,2-b:2',3'-a]thien-2-yl}-2-cyanoacrylic acid
• CAS: 1422273-15-1
• 化学式: C₅₄H₈₁NO₅S₃
• 分子量: 920.439
• InChiKey: IGLZYJGKQIVCSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.74
• 重原子数：
  63.0
• 可旋转键数：
  39.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.78
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-溴-1,2,3-三(十二烷氧基)苯 在 四(三苯基膦)钯 、 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 72.5h， 生成 3-{6-[3,4,5-tris(dodecyloxy)phenyl]dithieno[3,2-b:2',3'-a]thien-2-yl}-2-cyanoacrylic acid
  参考文献：
  名称：

  Synthesis of metal-free organic dyes containing tris(dodecyloxy)phenyl and dithienothiophenyl units and a study of their mesomorphic and photovoltaic properties

  摘要：

  In this study we synthesized three metal-free organic dyes (Cpd11, Cpd16, and Cpd22) featuring 3,4,5-tris(dodecyloxy)phenyl and cyanoacrylic acid moieties as electron-donor and electron-acceptor/anchoring units, respectively, linked through various dithienothiophenyl conjugated spacers. Cpd16 exhibits mesomorphic properties, confirmed through polarizing optical microscopy, differential scanning calorimetly, and X-ray diffraction (XRD), due to the appropriate ratio of the lengths of its flexible chain to its rigid core. Molecular modeling of Cpd16, and its d-spacing determined from XRD data, verified the existence of a tilt angle in the SmC phase. Among these metal-free organic dyes, a dye-sensitized solar cell incorporating Cpd16 exhibited the best performance, presumably because of its better packing and its mesomorphic properties; the power conversion efficiency was 3.72% (V-oc=0.58 V; J(sc)=9.98 mA cm(-2); FF=0.65) under simulated AM 1.5 irradiation (100 mW cm(-2)). (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.009