4,5-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)benzene-1,2-diamine | 1145919-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,5-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)benzene-1,2-diamine
• CAS: 1145919-75-0
• 化学式: C₃₄H₄₀N₂S₄
• 分子量: 604.969
• InChiKey: ARSDMGFUQIUXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.01
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4,5-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)benzene-1,2-diamine 、 环己六酮八水合物 以 溶剂黄146 为溶剂， 反应 24.0h， 以70%的产率得到6,7,16,17,26,27-Hexakis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-3,10,13,20,23,30-hexazaheptacyclo[20.8.0.02,11.04,9.012,21.014,19.024,29]triaconta-1(30),2,4(9),5,7,10,12,14(19),15,17,20,22,24(29),25,27-pentadecaene
  参考文献：
  名称：

  Starburst substituted hexaazatriphenylene compounds: synthesis, photophysical and electrochemical properties

  摘要：

  Starburst-substituted hexaazatriphenylene Compounds have been designed and synthesized by introducing various peripheral aryl substituents to the central heterocyclic core. The effects of various substituent groups on the photophysical and electrochemical properties of the substituted hexaazatriphenylene have been investigated. Significant red-shifts of the absorption peak (from 413 nm to 530 nm) and emission peak (from 432 nm to 700 nm) were observed when the electron-donating ability of the aryl substituents was increased, corresponding to a decrease in the band gap from 2.90 eV to 2.05 eV. Introducing bulky substituents with weak electron-donating ability enhances the fluorescence quantum yield from 23% to 87%. In contrast, incorporating aryl substituents with strong electron-donating ability decreases the fluorescence quantum yield. Also, due to the extended conjugation between the aryl substituents and the hexaazatriphenylene core, the reduction potentials of the compounds were reduced and the LUMO levels were thus increased. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.126
• 作为产物：
  描述：

  4,5-二溴-1,2-苯二胺 、 (5'-己基-[2,2'-联噻吩]-5-基)三丁基锡 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到4,5-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)benzene-1,2-diamine
  参考文献：
  名称：

  Starburst substituted hexaazatriphenylene compounds: synthesis, photophysical and electrochemical properties

  摘要：

  Starburst-substituted hexaazatriphenylene Compounds have been designed and synthesized by introducing various peripheral aryl substituents to the central heterocyclic core. The effects of various substituent groups on the photophysical and electrochemical properties of the substituted hexaazatriphenylene have been investigated. Significant red-shifts of the absorption peak (from 413 nm to 530 nm) and emission peak (from 432 nm to 700 nm) were observed when the electron-donating ability of the aryl substituents was increased, corresponding to a decrease in the band gap from 2.90 eV to 2.05 eV. Introducing bulky substituents with weak electron-donating ability enhances the fluorescence quantum yield from 23% to 87%. In contrast, incorporating aryl substituents with strong electron-donating ability decreases the fluorescence quantum yield. Also, due to the extended conjugation between the aryl substituents and the hexaazatriphenylene core, the reduction potentials of the compounds were reduced and the LUMO levels were thus increased. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.126