1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene | 1186018-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene
• 英文别名: 1,8-Dibromo-4,5-diheptylthieno[3,2-e][1]benzothiole
• CAS: 1186018-09-6
• 化学式: C₂₄H₃₂Br₂S₂
• 分子量: 544.458
• InChiKey: KZVKTLRYKXEZHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene 在 正丁基锂 、 copper dichloride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以65%的产率得到1-Bromo-8-(1-bromo-4,5-diheptylthieno[3,2-e][1]benzothiol-8-yl)-4,5-diheptylthieno[3,2-e][1]benzothiole
  参考文献：
  名称：

  Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization

  摘要：

  The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.

  DOI：

  10.1021/jo901769c
• 作为产物：
  描述：

  (1,8-Dibromo-4,5-diheptyl-2-trimethylsilylthieno[3,2-e][1]benzothiol-7-yl)-trimethylsilane 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 以94%的产率得到1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene
  参考文献：
  名称：

  Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization

  摘要：

  The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.

  DOI：

  10.1021/jo901769c

文献信息

• Functionalized Thiophene-Based [7]Helicene: Chirooptical Properties versus Electron Delocalization
  作者：Andrzej Rajca、Maren Pink、Shuzhang Xiao、Makoto Miyasaka、Suchada Rajca、Kausik Das、Kristin Plessel

  DOI：10.1021/jo901769c

  日期：2009.10.2

  The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.