5,5'-bis(tert-butylethynyl)-2,2'-bithiophene | 1294464-50-8

• 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: 5,5'-bis(tert-butylethynyl)-2,2'-bithiophene
• 英文别名: 2-(3,3-Dimethylbut-1-ynyl)-5-[5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl]thiophene；2-(3,3-dimethylbut-1-ynyl)-5-[5-(3,3-dimethylbut-1-ynyl)thiophen-2-yl]thiophene
• CAS: 1294464-50-8
• 化学式: C₂₀H₂₂S₂
• 分子量: 326.527
• InChiKey: CZXXATVDGGODTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  5,5'-二溴-2,2'-联噻吩 、 3,3-二甲基-1-丁炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到5,5'-bis(tert-butylethynyl)-2,2'-bithiophene
  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

• Microporous Polymers, Methods for the Preparation Thereof, and Uses Thereof
  申请人：The University of Liverpool

  公开号：US20140249239A1

  公开（公告）日：2014-09-04

  A method for preparing a conjugated microporous polymer comprises the coupling of an alkynyl aryl monomer having a plurality of terminal alkyne groups with an iodo- or bromo-aryl monomer having a plurality of halogen atoms in the presence of a palladium (0) catalyst. The conjugated microporous polymer comprises nodes comprising at least one aryl unit and struts comprising at least one alkyne unit and at least one aryl unit, wherein a node is bonded from its aryl unit or units to at least two struts via alkyne units. Such polymers are useful in numerous areas such as separations, controlled release, gas storage and supports for catalysts.
• US8809409B2
  申请人：——

  公开号：US8809409B2

  公开（公告）日：2014-08-19
• 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.