(E)-1,2-bis(2-(3,4-ethylenedioxy)thienyl)vinylene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,2-bis(2-(3,4-ethylenedioxy)thienyl)vinylene
• 英文别名: trans-bis(3,4-ethylenedioxythiophene)ethene；5-[(E)-2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)ethenyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine
• 化学式: C₁₄H₁₂O₄S₂
• 分子量: 308.379
• InChiKey: IEGWEAJMSWAYIW-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 (E)-1,2-bis(2-(3,4-ethylenedioxy)thienyl)vinylene 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 15.0h， 以100%的产率得到trans-bis(3,4-ethylenedioxythiophene)vinylene biscarbaldehyde
  参考文献：
  名称：

  Effect of the bridge substitution on the efficiency of dye-sensitized solar cells

  摘要：

  We have designed and synthesized a novel D-pi-A dye based on zinc porphyrin as the donor, cyanoacrylic acid as the acceptor and trans-bis(3,4-ethylenedioxythiophene)vinylene as the bridge. Under standard global AM 1.5 solar conditions, the Zn-porphyrin-2-EDOT sensitizer based cell gave a J(SC) of 7.28 mA cm(-2), V-OC of 0.438 V was obtained with a FF of 0.514, corresponding to an overall conversion efficiency eta = 1.64%. The reasons for this low efficiency are analyzed to try to develop knowledge for future dye designing. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.091
• 作为产物：
  描述：

  2,3-二氢噻吩并[3,4-b][1,4]二噁英-5-甲醇 在 碘 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 (E)-1,2-bis(2-(3,4-ethylenedioxy)thienyl)vinylene
  参考文献：
  名称：

  Effect of the bridge substitution on the efficiency of dye-sensitized solar cells

  摘要：

  We have designed and synthesized a novel D-pi-A dye based on zinc porphyrin as the donor, cyanoacrylic acid as the acceptor and trans-bis(3,4-ethylenedioxythiophene)vinylene as the bridge. Under standard global AM 1.5 solar conditions, the Zn-porphyrin-2-EDOT sensitizer based cell gave a J(SC) of 7.28 mA cm(-2), V-OC of 0.438 V was obtained with a FF of 0.514, corresponding to an overall conversion efficiency eta = 1.64%. The reasons for this low efficiency are analyzed to try to develop knowledge for future dye designing. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.091

文献信息

• Poly[trans-bis(3,4-ethylenedioxythiophene)vinylene]: a low band-gap polymer with rapid redox switching capabilities between conducting transmissive and insulating absorptive states
  作者：Gregory A. Sotzing、John R. Reynolds

  DOI：10.1039/c39950000703

  日期：——

  trans-Bis(3,4-ethylenedioxythiophene)vinylene is synthesized and electrochemically polymerized to give poly[trans-bis(3,4-ethylenedioxythiophene)vinylene](PBEDOT-V) which exhibits a band gap of 1.4 eV and can be rapidly switched between insulating deep purple absorptive and highly conducting light blue transmissive states.

  合成反式双(3,4-乙撑二氧噻吩)亚乙烯基并进行电化学聚合得到聚[反式双(3,4-乙撑二氧噻吩)亚乙烯基](PBEDOT-V)，其带隙为1.4 eV并且可以快速切换介于绝缘的深紫色吸收态和高导电的浅蓝色透射态之间。