2,5-bis(tert-butylethynyl)thieno[3,2-b]thiophene | 1294464-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 2,5-bis(tert-butylethynyl)thieno[3,2-b]thiophene
• 英文别名: 2,5-Bis(3,3-dimethylbut-1-ynyl)thieno[3,2-b]thiophene；2,5-bis(3,3-dimethylbut-1-ynyl)thieno[3,2-b]thiophene
• CAS: 1294464-48-4
• 化学式: C₁₈H₂₀S₂
• 分子量: 300.489
• InChiKey: RFOIPKIIWNQWPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二溴噻吩并[3,2-B]噻吩 、 3,3-二甲基-1-丁炔 在 copper(l) iodide 、 palladium diacetate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以86%的产率得到2,5-bis(tert-butylethynyl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  Enhanced absorption and fluorescence efficiency of silylethynyl-functionalized oligothiophenes and thieno[3,2–b]thiopahene

  摘要：

  Silylethynyl-substituted oligothiophenes and thieno[3,2-b] thiophene were synthesized by the Sonogashira coupling reaction. The absorption and fluorescence maxima of these compounds shifted to longer wavelength, and they exhibited higher absorption coefficients and quantum yields than the corresponding unsubstituted molecules and tert-butylethynyl derivatives. From the DFT calculation, the energy band gap between HOMO and LUMO decreases by the introduction of a silicon atom. Thus, silyl groups can play important role in enhancing the quantum efficiency and decreasing the band-gap of chromophores. Hence, Silylethynyl group can serve as a highly efficient auxiliary for use in optical devices. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.044

文献信息

• Enhanced absorption and fluorescence efficiency of silylethynyl-functionalized oligothiophenes and thieno[3,2–b]thiopahene
  作者：Kengo Asai、Gen-ichi Konishi、Yumiko Nakajima、Susumu Kawauchi、Fumiyuki Ozawa、Kazuhiko Mizuno

  DOI：10.1016/j.jorganchem.2010.10.044

  日期：2011.3

  Silylethynyl-substituted oligothiophenes and thieno[3,2-b] thiophene were synthesized by the Sonogashira coupling reaction. The absorption and fluorescence maxima of these compounds shifted to longer wavelength, and they exhibited higher absorption coefficients and quantum yields than the corresponding unsubstituted molecules and tert-butylethynyl derivatives. From the DFT calculation, the energy band gap between HOMO and LUMO decreases by the introduction of a silicon atom. Thus, silyl groups can play important role in enhancing the quantum efficiency and decreasing the band-gap of chromophores. Hence, Silylethynyl group can serve as a highly efficient auxiliary for use in optical devices. (C) 2010 Elsevier B.V. All rights reserved.