5,5'-bis(5-bromo-3-decylthiophen-2-yl)-2,2'-bithiazole | 1394238-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5,5'-bis(5-bromo-3-decylthiophen-2-yl)-2,2'-bithiazole
• CAS: 1394238-04-0
• 化学式: C₃₄H₄₆Br₂N₂S₄
• 分子量: 770.825
• InChiKey: OMNUUOBXFNIQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.61
• 重原子数：
  42.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,5'-bis(5-bromo-3-decylthiophen-2-yl)-2,2'-bithiazole 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到5,5'-bis(2-triphenylamino-3-decylthiophene-2-yl)-2,2'-bithiazole
  参考文献：
  名称：

  Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells

  摘要：

  Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2,2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl) thiazolo[5,4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm(2) illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1: 3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm(2), an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm(2), an open circuit voltage of 0.94 V, and a fill factor of 0.39. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.11.016
• 作为产物：
  描述：

  5,5'-bis(3-decylthiophen-2-yl)-2,2'-bithiazole 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以72%的产率得到5,5'-bis(5-bromo-3-decylthiophen-2-yl)-2,2'-bithiazole
  参考文献：
  名称：

  Synthesis and characterization of triphenylamine flanked thiazole-based small molecules for high performance solution processed organic solar cells

  摘要：

  Two new small molecules, 5,5-bis(2-triphenylamino-3-decylthiophen-2-yl)-2,2-bithiazole (M1) and 2,5-bis(2-triphenylamino-3-decylthiophen-2-yl) thiazolo[5,4-d]thiazole (M2) based on an electron-donor triphenylamine unit and electron-acceptor thiophene-thiazolothiazole or thiophene-bithiazole units were synthesized by a palladium(0)-catalyzed Suzuki coupling reaction and examined as donor materials for application in organic solar cells. The small molecules had an absorption band in the range of 300-560 nm, with an optical band gap of 2.22 and 2.25 for M1 and M2, respectively. As determined by cyclic voltammetry, the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of M1 were -5.27 eV and -3.05 eV, respectively, which were 0.05 eV and 0.02 eV greater than that of M2. Photovoltaic properties of the small molecules were investigated by constructing bulk-heterojunction organic solar cell (OSC) devices using M1 and M2 as donors and fullerene derivatives, 6,6-phenyl-C61-butyric acid methyl ester (PC61BM) and 6,6-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptors with the device architecture ITO/PEDOT:PSS/M1 or M2:PCBM/LiF/Al. The effect of the small molecule/fullerene weight ratio, active layer thickness, and processing solvent were carefully investigated to improve the performance of the OSCs. Under AM 1.5 G 100 mW/cm(2) illumination, the optimized OSC device with M1 and PC71BM at a weight ratio of 1: 3 delivered a power conversion efficiency (PCE) of 1.30%, with a short circuit current of 4.63 mA/cm(2), an open circuit voltage of 0.97 V, and a fill factor of 0.29. In contrast, M2 produced a better performance under identical device conditions. A PCE as high as 2.39% was recorded, with a short circuit current of 6.49 mA/cm(2), an open circuit voltage of 0.94 V, and a fill factor of 0.39. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.11.016