3,4-ethylenedioxy-5-bromo-2,2'-bithiophene | 295358-40-6

• 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: 3,4-ethylenedioxy-5-bromo-2,2'-bithiophene
• 英文别名: 5-bromo-3,4-ethylenedioxy-2,2'-bithienyl；5-Bromo-7-thiophen-2-yl-2,3-dihydrothieno[3,4-b][1,4]dioxine
• CAS: 295358-40-6
• 化学式: C₁₀H₇BrO₂S₂
• 分子量: 303.2
• InChiKey: DKPJQLNPEJBNGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-ethylenedioxy-5-bromo-2,2'-bithiophene 在 正丁基锂 、 copper dichloride 作用下， 以42%的产率得到dithienyl-bis(3,4-ethylenedioxythiophene)
  参考文献：
  名称：

  Mixed π-conjugated oligomers of thiophene and 3,4-ethylenedioxythiophene (EDOT)

  摘要：

  Conjugated oligomers based on various combinations of thiophene and 3,4-ethylenedioxythiophene (EDOT) moieties have been synthesised. Comparison of the optical and electrochemical properties shows that the introduction of a bis-EDOT core in the middle of the system produces a decrease of the HOMO-LUMO gap which is attributed to an enhancement of the planarity and rigidity of the pi-conjugated system. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00888-1
• 作为产物：
  描述：

  三丁基(2,3-二氢噻吩并[3,4-b]-[1,4]二恶英-5-基)锡烷 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 、 甲苯 为溶剂， 生成 3,4-ethylenedioxy-5-bromo-2,2'-bithiophene
  参考文献：
  名称：

  Mixed π-conjugated oligomers of thiophene and 3,4-ethylenedioxythiophene (EDOT)

  摘要：

  Conjugated oligomers based on various combinations of thiophene and 3,4-ethylenedioxythiophene (EDOT) moieties have been synthesised. Comparison of the optical and electrochemical properties shows that the introduction of a bis-EDOT core in the middle of the system produces a decrease of the HOMO-LUMO gap which is attributed to an enhancement of the planarity and rigidity of the pi-conjugated system. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00888-1

文献信息

• Synthesis and properties of end-capped bis(oligothienyl) sulfides
  作者：Daniel J. T Myles、M’hamed Chahma、Robin G Hicks

  DOI：10.1139/v08-128

  日期：2008.10.1

  chroromophores oligothiophenes des sulfures d'oligothienyle. Les etudes de voltamperometrie cyclique sur les sulfures de bis(oligothienyle) revelent que ces especes peuvent etre oxydees d'une facon reversible en cations radicaux, mais que la reversibilite des oxydations subsequentes depend de la longueur de la chaine oligothienyle et de la presence et de la position de groupes ethylenedioxythiophene

  在一个效应 la 合成 d'une serie de bis(oligothienyl)sulfures fermes aux extremites par des groupes mesitylthio (MesS-) et on en a确定 les proprietes optiques etelectrochimiques rapportees ici。Les produits recherches ont ete synthetices par des protocoles converents dans lesquels une serie d'oligomeres Court du thiophene portant un 替代物终端 mesitylthio sont d'abord assembles par des reactors de couplage croises
• Direct C–H arylation of 3-methoxythiophene catalyzed by Pd. Application to a more efficient synthesis of π-alkoxy-oligothiophene derivatives
  作者：A. Borghese、G. Geldhof、L. Antoine

  DOI：10.1016/j.tetlet.2006.10.130

  日期：2006.12

  The direct regioselective C-H arylation of 3-methoxythiophene and 3,4-ethylenedioxythiophene (EDOT) was performed successfully under 'Heck-type' experimental conditions. This novel synthetic methodology has been used to prepare in a more simple way a series of oligothiophenes interesting for the electronic industry to build new synthetic organic materials. (c) 2006 Elsevier Ltd. All rights reserved.