2-Methylhexan-2-yl 2-bromo-5-[4-[5-bromo-4-(2-methylhexan-2-yloxycarbonyl)thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophene-3-carboxylate | 1248336-13-1

• 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: 2-Methylhexan-2-yl 2-bromo-5-[4-[5-bromo-4-(2-methylhexan-2-yloxycarbonyl)thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophene-3-carboxylate
• 英文别名: 2-methylhexan-2-yl 2-bromo-5-[4-[5-bromo-4-(2-methylhexan-2-yloxycarbonyl)thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophene-3-carboxylate
• CAS: 1248336-13-1
• 化学式: C₃₀H₃₄Br₂N₂O₄S₃
• 分子量: 742.617
• InChiKey: ALCOEHYIFYDWCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  163
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methylhexan-2-yl 2-bromo-5-[4-[5-bromo-4-(2-methylhexan-2-yloxycarbonyl)thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophene-3-carboxylate
  参考文献：
  名称：

  Influence of the Annealing Temperature on the Photovoltaic Performance and Film Morphology Applying Novel Thermocleavable Materials

  摘要：

  Di-2-thienyl-2,1,3-benzothiadiazole (DTBT) bearing thermally cleavable ester groups in different positions were prepared and copolymerized with alkylsubstituted cyclopentadithiophene (CPDT). The polymers were found to have band gaps in the range of 1.66-2.03 eV and were explored in polymer photovoltaic devices as mixtures with soluble methanofullerenes. The positioning of the ester groups proved to be very significant despite the identical conjugated backbone of 2-methyl-2-hexyl 5-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)-2-(7-(3-(((2-methylhexan-2-yl)oxy)-carbonyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-3-carboxylate (T1) and 2-methyl-2-hexyl 2-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)-5-(7-(4-(((2-methylhexan-2-yl)oxy)carbonyl)thiophen-2-yObenzokl[1,2,5]thiadiazol-4-yl)thiophene-3-carboxylate (T2). Power conversion efficiencies of up to 1.92% were observed for polymers bearing ester groups on the 4-positions of the thienyl groups (T2), but shifting them to the 3-positions (T1) reduced the efficiency significantly to 0.18%. The thermal behavior of the polymers was studied with thermogravimetric analysis (TGA) that showed a weight loss around 200 degrees C corresponding to elimination of the ester side chains followed by a second weight loss around 300 degrees C corresponding to loss of CO2 via decarboxylation. The temperature of thermocleavage of the active layer films was optimized to 265 degrees C whereby the T2:PCBM solar cells maintained a significant performance giving efficiencies up to 1.49%.

  DOI：

  10.1021/cm1019537

文献信息

• Influence of the Annealing Temperature on the Photovoltaic Performance and Film Morphology Applying Novel Thermocleavable Materials
  作者：Martin Helgesen、Morten Bjerring、Niels Chr. Nielsen、Frederik C. Krebs

  DOI：10.1021/cm1019537

  日期：2010.10.12

  Di-2-thienyl-2,1,3-benzothiadiazole (DTBT) bearing thermally cleavable ester groups in different positions were prepared and copolymerized with alkylsubstituted cyclopentadithiophene (CPDT). The polymers were found to have band gaps in the range of 1.66-2.03 eV and were explored in polymer photovoltaic devices as mixtures with soluble methanofullerenes. The positioning of the ester groups proved to be very significant despite the identical conjugated backbone of 2-methyl-2-hexyl 5-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)-2-(7-(3-(((2-methylhexan-2-yl)oxy)-carbonyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazol-4-yl)thiophene-3-carboxylate (T1) and 2-methyl-2-hexyl 2-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophen-2-yl)-5-(7-(4-(((2-methylhexan-2-yl)oxy)carbonyl)thiophen-2-yObenzokl[1,2,5]thiadiazol-4-yl)thiophene-3-carboxylate (T2). Power conversion efficiencies of up to 1.92% were observed for polymers bearing ester groups on the 4-positions of the thienyl groups (T2), but shifting them to the 3-positions (T1) reduced the efficiency significantly to 0.18%. The thermal behavior of the polymers was studied with thermogravimetric analysis (TGA) that showed a weight loss around 200 degrees C corresponding to elimination of the ester side chains followed by a second weight loss around 300 degrees C corresponding to loss of CO2 via decarboxylation. The temperature of thermocleavage of the active layer films was optimized to 265 degrees C whereby the T2:PCBM solar cells maintained a significant performance giving efficiencies up to 1.49%.