tetrathiafulvalene-2-carboxylic acid prop-2-ynylamide | 1264657-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: tetrathiafulvalene-2-carboxylic acid prop-2-ynylamide
• 英文别名: 2-(1,3-dithiol-2-ylidene)-N-prop-2-ynyl-1,3-dithiole-4-carboxamide
• CAS: 1264657-14-8
• 化学式: C₁₀H₇NOS₄
• 分子量: 285.436
• InChiKey: JOFLWWNUGCZDEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(azidomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine 、 tetrathiafulvalene-2-carboxylic acid prop-2-ynylamide 在 tetrakis(acetonitrile)copper(I) hexafluorophosphate 、 铜 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以37%的产率得到tetrathiafulvalene-2-carboxylic acid (1-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethyl)-1H-[1,2,3]triazol-4-ylmethyl)amide
  参考文献：
  名称：

  Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via ‘click’-reaction

  摘要：

  The possibility to functionalize polymers after a successful polymerization process is often an important challenge in macromolecular science. Herein, modified electrodes based on azide-containing potentio-dynamically electropolymerized PEDOT derivatives are reported. This reactive coatings are subsequently modified under mild heterogeneous conditions by copper-catalyzed Huisgen 1,3-dipolar cycloaddition with terminal alkynes, the so-called 'click'-reaction. A series of terminal alkynes have been successfully used for the facile immobilization of neutral, electron-accepting and electron-donating units to the conducting PEDOT with high conversion efficiencies showing the broad scope of the strategy. The route is devoid of the limitations generated by the various steric and electronic impacts of the substituents when attached to the monomer before polymerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.022
• 作为产物：
  描述：

  tetrathiafulvalene-3-carbonyl chloride 、 炔丙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以57%的产率得到tetrathiafulvalene-2-carboxylic acid prop-2-ynylamide
  参考文献：
  名称：

  Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via ‘click’-reaction

  摘要：

  The possibility to functionalize polymers after a successful polymerization process is often an important challenge in macromolecular science. Herein, modified electrodes based on azide-containing potentio-dynamically electropolymerized PEDOT derivatives are reported. This reactive coatings are subsequently modified under mild heterogeneous conditions by copper-catalyzed Huisgen 1,3-dipolar cycloaddition with terminal alkynes, the so-called 'click'-reaction. A series of terminal alkynes have been successfully used for the facile immobilization of neutral, electron-accepting and electron-donating units to the conducting PEDOT with high conversion efficiencies showing the broad scope of the strategy. The route is devoid of the limitations generated by the various steric and electronic impacts of the substituents when attached to the monomer before polymerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.022

文献信息

• Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via ‘click’-reaction
  作者：Hang-Beom Bu、Günther Götz、Egon Reinold、Astrid Vogt、Sylvia Schmid、José L. Segura、Raúl Blanco、Rafael Gómez、Peter Bäuerle

  DOI：10.1016/j.tet.2010.12.022

  日期：2011.2

  The possibility to functionalize polymers after a successful polymerization process is often an important challenge in macromolecular science. Herein, modified electrodes based on azide-containing potentio-dynamically electropolymerized PEDOT derivatives are reported. This reactive coatings are subsequently modified under mild heterogeneous conditions by copper-catalyzed Huisgen 1,3-dipolar cycloaddition with terminal alkynes, the so-called 'click'-reaction. A series of terminal alkynes have been successfully used for the facile immobilization of neutral, electron-accepting and electron-donating units to the conducting PEDOT with high conversion efficiencies showing the broad scope of the strategy. The route is devoid of the limitations generated by the various steric and electronic impacts of the substituents when attached to the monomer before polymerization. (C) 2010 Elsevier Ltd. All rights reserved.