2-{2-[1-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-isoindole-1,3-dione | 1028449-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-{2-[1-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-isoindole-1,3-dione
• 英文别名: 2-[2-[1-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-3-ylmethyl)triazol-4-yl]ethyl]isoindole-1,3-dione；2-[2-[1-(2,3-dihydrothieno[3,4-b][1,4]dioxin-3-ylmethyl)triazol-4-yl]ethyl]isoindole-1,3-dione
• CAS: 1028449-15-1
• 化学式: C₁₉H₁₆N₄O₄S
• 分子量: 396.426
• InChiKey: XSXOVPVVAZHKIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(氯甲基)-2,3-二氢-噻吩并[3,4-b]-1,4-二噁英 在 sodium azide 、 tetrakis(acetonitrile)copper(I) hexafluorophosphate 、 铜 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 75.0h， 生成 2-{2-[1-(2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethyl)-1H-[1,2,3]triazol-4-yl]-ethyl}-isoindole-1,3-dione
  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

• “Click”-functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT)
  作者：Hang-Beom Bu、Günther Götz、Egon Reinold、Astrid Vogt、Sylvia Schmid、Raúl Blanco、Jose L. Segura、Peter Bäuerle

  DOI：10.1039/b718077b

  日期：——

  Efficient post-functionalization of conductive polymer films was achieved by Cu+-catalyzed 'click'-cycloaddition of novel poly(azidomethyl-EDOT) P2 and various functionalized terminal alkynes under mild heterogeneous conditions with high conversion efficiencies.

  通过在温和的异相条件下，采用Cu+催化的新型聚（叠氮甲基-EDOT）P2与各种功能化末端炔烃的‘点击’环加成，实现了导电聚合物薄膜的高效后功能化，具有高转化效率。
• 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.