2-(p-iodophenylethynyl)thiophene | 743436-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-iodophenylethynyl)thiophene
• 英文别名: 2-[2-(4-Iodophenyl)ethynyl]thiophene；2-[2-(4-iodophenyl)ethynyl]thiophene
• CAS: 743436-36-4
• 化学式: C₁₂H₇IS
• 分子量: 310.158
• InChiKey: TWCUCXFXPIJEPX-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C
• 沸点：
  368.5±22.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(p-iodophenylethynyl)thiophene 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 二乙胺 作用下， 以 甲苯 为溶剂， 反应 27.0h， 生成 2,5-di-[2-(thienylethynyl)(phenylethynyl)]thiophene
  参考文献：
  名称：

  Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties

  摘要：

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.032
• 作为产物：
  描述：

  (4-iodobenzyl)triphenylphosphonium bromide 在 potassium tert-butylate 、 溴 、 碘 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 80.5h， 生成 2-(p-iodophenylethynyl)thiophene
  参考文献：
  名称：

  Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties

  摘要：

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.032

文献信息

• Synthesis and Structural Properties of Cyclophanes Containing Thiophene Rings in the Side-chain
  作者：Aldo Taticchi、Assunta Marrocchi、Lucio Minuti、Selvaggia Landi、Eszter Gacs-Baitz

  DOI：10.3987/com-06-10736

  日期：——

  The synthesis of some cyclophanes bearing in the linear side-chain carbon-carbon triple bonds conjugated with thiophene rings has been reported. Structure analysis of the products based on extensive NMR investigation is presented. UV-Vis absorption spectra and fluorescence spectra have been measured. The analysis of the spectra points out a correlation between the maxima and the structure of the side-chain. The replacement of a benzene ring with a thiophene ring causes a bathochromic shift when the benzene ring close to the paracyclophane moiety is replaced.
• Synthesis of conjugated 2-arylethynyl and 2-arylethenyl thiophene structures with optical properties
  作者：J.Gonzalo Rodrı́guez、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tetlet.2004.05.104

  日期：2004.7

  Conjugated mono(arylethynyl)oligothiophene structures have been obtained starting with (E)-[1-(2'-thienyl)-2-(p-phenyl)]ethyne (E)-7 and 2-[p-(iodophenyl)ethynyl]thiophene 8. Conjugated nanostructures were synthesized by oxidative coupling between the terminal acetylenes (E)-7 and 8 to give, respectively, 1,4-di[(2-p-(iodophenyl)ethynyl)thienyl]-1,3-butadiyne and 1,4-di[(2-p-iodophenylethynyl)thienyl]-1,3-butadiyne. All the thiophene derivatives synthesized show an important fluorescence radiation emission, with a bathochromic shift, which increases with the conjugation of the chain. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of conjugated 2 and 2,5-(ethenyl) and (ethynyl)phenylethynyl thiophenes: fluorescence properties
  作者：J. Gonzalo Rodriguez、Jorge Esquivias、Antonio Lafuente、Laura Rubio

  DOI：10.1016/j.tet.2006.01.032

  日期：2006.3

  Nano conjugated thienylethenyl and thienylethynyl Compounds with controlled Structure and dimensions have been efficiently prepared, by heterocoupling reaction between 1,4-(thienylethynylphenyl)phenylacetylene (or thienylethenyl)phenylacetylene and 2- or 2,5-dihalothiophene. Conjugated 1,4-di(2-thienylethynylphenyl)- (or 2-thienylethenylphenyl)-1,3-butadiyne were obtained by the homocoupling of the terminal acetylenes in excellent yield. The end-capped (N,N-dimethylaminophenyl)- and [3,5-di(trimethylsilylethynyl)-1-ethynyl]-2,5-di(iodo)thiophene were obtained by the heterocoupling between the corresponding terminal acetylene and 2,5-di(iodo)thiophene, catalyzed by the bis(triphenylphosphine)palladium and cuprous iodide system in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.