4,8-bis(thiophen-2-yl)-5H-[1,2,5]thiadiazolo[3,4-f]benzotriazole | 1307899-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,8-bis(thiophen-2-yl)-5H-[1,2,5]thiadiazolo[3,4-f]benzotriazole
• CAS: 1307899-45-1
• 化学式: C₁₄H₇N₅S₃
• 分子量: 341.441
• InChiKey: ZBRGLPWGPRFVGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.35
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-bromo-3-methyloctane 、 4,8-bis(thiophen-2-yl)-5H-[1,2,5]thiadiazolo[3,4-f]benzotriazole 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4,8-二(5-溴噻吩-2-基)-6-(2-乙基己基)-[1,2,5]噻二唑[3,4-F]苯并三氮唑
  参考文献：
  名称：

  Synthesis of novel narrow-band-gap copolymers based on [1,2,5]thiadiazolo[3,4-f]benzotriazole and their application in bulk-heterojunction photovoltaic devices

  摘要：

  Two novel conjugated alternating copolymers with [1,2,5]thiadiazolo[3,4-f]benzotriazole as acceptor and 9,9-dioctylfluorene or N-9'-heptadecanyl-carbazole as donors respectively, were synthesized by Suzuki polycondensation. Both of the two copolymers have nearly ideal band gaps and show excellent absorption spectra in near infrared region. Polymer solar cells based on the blends of them and [6,6]-phenyl-C-71 butyric acid methyl ester show excellent performance when using a water/alcohol soluble conjugated polymer as cathode interlayer, which exhibit a maximum power conversion efficiency of 3.17% with the short-circuit current density of 8.50 mA/cm(2), the open-circuit voltage of 0.70 V and the fill factor of 41%. Our results demonstrate that [1,2,5]thiadiazolo[3,4-f]benzotriazole is a promising acceptor unit for low band gap polymer donor materials design. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.02.014
• 作为产物：
  描述：

  4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole-5,6-diamine 在 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 生成 4,8-bis(thiophen-2-yl)-5H-[1,2,5]thiadiazolo[3,4-f]benzotriazole
  参考文献：
  名称：

  Synthesis of novel narrow-band-gap copolymers based on [1,2,5]thiadiazolo[3,4-f]benzotriazole and their application in bulk-heterojunction photovoltaic devices

  摘要：

  Two novel conjugated alternating copolymers with [1,2,5]thiadiazolo[3,4-f]benzotriazole as acceptor and 9,9-dioctylfluorene or N-9'-heptadecanyl-carbazole as donors respectively, were synthesized by Suzuki polycondensation. Both of the two copolymers have nearly ideal band gaps and show excellent absorption spectra in near infrared region. Polymer solar cells based on the blends of them and [6,6]-phenyl-C-71 butyric acid methyl ester show excellent performance when using a water/alcohol soluble conjugated polymer as cathode interlayer, which exhibit a maximum power conversion efficiency of 3.17% with the short-circuit current density of 8.50 mA/cm(2), the open-circuit voltage of 0.70 V and the fill factor of 41%. Our results demonstrate that [1,2,5]thiadiazolo[3,4-f]benzotriazole is a promising acceptor unit for low band gap polymer donor materials design. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.02.014