(5-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane | 1448337-60-7

• 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-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane
• 英文别名: (5-Bromothiophen-2-yl)-bis[5-[5-[tert-butyl(dimethyl)silyl]thiophen-2-yl]thiophen-2-yl]-methylsilane
• CAS: 1448337-60-7
• 化学式: C₃₃H₄₃BrS₅Si₃
• 分子量: 764.195
• InChiKey: YLOJYIITKYWQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异丙醇频哪醇硼酸酯 、 (5-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以38%的产率得到Bis[5-[5-[tert-butyl(dimethyl)silyl]thiophen-2-yl]thiophen-2-yl]-methyl-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]silane
  参考文献：
  名称：

  Synthesis and optical properties of H-shaped silicon-containing molecule with bithiophene units

  摘要：

  The H-shaped molecule, 5,5'-bis{[(5'-tert-butyldimethylsilyl)-2,2'-(bithiophen-5-yl)]methylsilyl}-2,2'-bithiophene (3) was prepared by the reaction of 5'-(tert-butyldimethylsilyl)-5-lithio-2,2'-bithiophene with 2-bromo-5-(dichloromethylsilyl)thiophene, followed by treatment of the resulting product (5-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane (1) with compound (2), obtained by the reaction of the lithiated derivative of 1 with 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, in the presence of dichlorobis(triphenylphosphine)palladium, as light yellow solids. Compound 3 showed absorption maximum (lambda(max)) at 336 nm with a molar absorption coefficient (epsilon) of 113,000 M-1 cm(-1) in dioxane. The fluorescence spectrum of 3 excited at 336 nm in dioxane displayed the emission maxima at 377 and 387 nm, with the fluorescence quantum yield of 48%. We also carried out theoretical treatment of compound 3 to elucidate the geometrical and electronic structure, using the Gaussian 03 program package, with the 6-31G and 6-31G(d) basis sets. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.05.024
• 作为产物：
  描述：

  2-bromo-5-(dichloromethylsilyl)thiophene 、 5-bromo-5'-tert-butyldimethylsilyl-2,2'-bithiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 以27%的产率得到(5-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane
  参考文献：
  名称：

  Synthesis and optical properties of H-shaped silicon-containing molecule with bithiophene units

  摘要：

  The H-shaped molecule, 5,5'-bis{[(5'-tert-butyldimethylsilyl)-2,2'-(bithiophen-5-yl)]methylsilyl}-2,2'-bithiophene (3) was prepared by the reaction of 5'-(tert-butyldimethylsilyl)-5-lithio-2,2'-bithiophene with 2-bromo-5-(dichloromethylsilyl)thiophene, followed by treatment of the resulting product (5-bromothiophen-2-yl)bis[5'-(tert-butyldimethylsilyl)-2,2'-bithiophen-5-yl](methyl)silane (1) with compound (2), obtained by the reaction of the lithiated derivative of 1 with 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, in the presence of dichlorobis(triphenylphosphine)palladium, as light yellow solids. Compound 3 showed absorption maximum (lambda(max)) at 336 nm with a molar absorption coefficient (epsilon) of 113,000 M-1 cm(-1) in dioxane. The fluorescence spectrum of 3 excited at 336 nm in dioxane displayed the emission maxima at 377 and 387 nm, with the fluorescence quantum yield of 48%. We also carried out theoretical treatment of compound 3 to elucidate the geometrical and electronic structure, using the Gaussian 03 program package, with the 6-31G and 6-31G(d) basis sets. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.05.024

文献信息

• Synthesis and optical properties of silyl-bridged H-shaped multi-thiophenes
  作者：Akinobu Naka、Kazuki Neishi、Munemasa Nishimoto、Mitsuo Ishikawa

  DOI：10.1016/j.jorganchem.2015.05.025

  日期：2015.8

  We have synthesized new types of the H-shaped molecules with bis(tert-butyldimethylsilylbithienyl) silyl and bis(tert-butyldimethylsilylterthienyl) silyl units by using Sonogashira coupling reaction. UV-Vis absorption and fluorescence properties of these molecules have been investigated. We have found that the disilanylene group in the H-shaped molecule with bis(tert-butyldimethylsilylbithienyl) silyl units plays an important role in enhancing the quantum efficiency in solution. (C) 2015 Elsevier B.V. All rights reserved.