2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid | 1608150-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid
• CAS: 1608150-03-3
• 化学式: C₁₉H₁₅BN₂O₃
• 分子量: 330.151
• InChiKey: AVEVYXNXDDECAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.37
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid 、 1,7-二溴代苝二酰亚胺 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 72.0h， 以80%的产率得到N,N'-bis(2,6-diisopropylphenyl)-1,7-bis[2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-yl]perylene-3,4,9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis, characterization and optoelectronic properties of a new perylene diimide–benzimidazole type solar light harvesting dye

  摘要：

  A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N'-bis(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.02.131
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 36.0h， 生成 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid
  参考文献：
  名称：

  Synthesis, characterization and optoelectronic properties of a new perylene diimide–benzimidazole type solar light harvesting dye

  摘要：

  A perylene diimide type small molecule (BI-PDI) has been synthesized through Suzuki coupling reaction between N,N'-bis(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic diimide and 2-(2-hydroxyphenyl)-7-phenyl-1H-benzimidazole-4-boronic acid. BI-PDI small molecule has showed an absorption band between 350 and 750 nm on thin films. HOMO and LUMO energy levels of BI-PDI dye have been calculated to be about -5.92 eV and -3.82 eV, respectively. Solution-processed bulk heterojunction (BHJ) solar cells have been constructed using BI-PDI as donor and [6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM) as acceptor or poly(3-hexylthiophene) (P3HT) as donor and BI-PDI as acceptor. The external quantum efficiencies (EQE) of the devices cover the most of the visible region between 400 and 700 nm for both configurations. Photovoltaic performances of BI-PDI-based organic solar cells are limited by the aggregation tendency of PDI structure and poor hole/electron mobilities of the active layer. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.02.131