2-trimethylsilylethynyl-5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophene | 940893-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-trimethylsilylethynyl-5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophene
• 英文别名: 2-[5-(5,5-Dimethyl-1,3-dioxan-2-yl)thiophen-2-yl]ethynyl-trimethylsilane
• CAS: 940893-09-4
• 化学式: C₁₅H₂₂O₂SSi
• 分子量: 294.49
• InChiKey: QKZFYDYZHQSMGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-trimethylsilylethynyl-5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophene 在 四(三苯基膦)钯 copper(l) iodide 、 镍 、 potassium carbonate 、 一水合肼 、 二乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 13.0h， 生成 2-(5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophen-2-yl)-6-aminobenzofuran
  参考文献：
  名称：

  Synthesis and Photovoltaic Properties of Efficient Organic Dyes Containing the Benzo[b]furan Moiety for Solar Cells

  摘要：

  New organic dyes composed of the benzo[b]furan donor, thiophene-conjugated bridge, and cyano acrylic acid acceptor have been newly synthesized through the one-pot coupling cyclization key step. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using this dye. A solar-to-electric conversion efficiency of 6.65% and 4.70% is achieved with 1 and 2, respectively.

  DOI：

  10.1021/jo0625150
• 作为产物：
  描述：

  2-(5-bromothiophen-2-yl)-5,5-dimethyl-1,3-dioxane 、 三甲基乙炔基硅 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 反应 8.0h， 以92%的产率得到2-trimethylsilylethynyl-5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophene
  参考文献：
  名称：

  Synthesis and Photovoltaic Properties of Efficient Organic Dyes Containing the Benzo[b]furan Moiety for Solar Cells

  摘要：

  New organic dyes composed of the benzo[b]furan donor, thiophene-conjugated bridge, and cyano acrylic acid acceptor have been newly synthesized through the one-pot coupling cyclization key step. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using this dye. A solar-to-electric conversion efficiency of 6.65% and 4.70% is achieved with 1 and 2, respectively.

  DOI：

  10.1021/jo0625150

文献信息

• Electronic Alteration on Oligothiophenes by <i>o</i>-Carborane: Electron Acceptor Character of <i>o</i>-Carborane in Oligothiophene Frameworks with Dicyano-Vinyl End-On Group
  作者：So-Yoen Kim、Ah-Rang Lee、Guo Fan Jin、Yang-Jin Cho、Ho-Jin Son、Won-Sik Han、Sang Ook Kang

  DOI：10.1021/acs.joc.5b00336

  日期：2015.5.1

  We studied electronic change in oligothiophenes by employing o-carborane into a molecular array in which one or both end(s) were substituted by electron-withdrawing dicyano-vinyl group(s). Depending on mono- or bis-substitution at the o-carborane, a series of linear A(1)-D-A(2) (1a-1c) or V-shaped A(1)-D-A(2)-D-A(1) (2a-2c) oligothiophene chain structures of variable length were prepared; A(1), D, and A(2), represent dicyano-vinyl, oligothiophenyl, and o-carboranyl groups, respectively. Among this series, 2a shows strong electron-acceptor capability of o-carborane comparable to that of the dicyano-vinyl substituent, which can be elaborated by a conformational effect driven by cage sigma-*-pi* interaction. As a result, electronic communications between o-carborane and dicyano-vinyl groups are successfully achieved in 2a.