4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]selenadiazole | 1613468-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]selenadiazole
• 英文别名: 4,7-Bis(thieno[3,2-b]thiophen-5-yl)-2,1,3-benzoselenadiazole；4,7-bis(thieno[3,2-b]thiophen-5-yl)-2,1,3-benzoselenadiazole
• CAS: 1613468-46-4
• 化学式: C₁₈H₈N₂S₄Se
• 分子量: 459.499
• InChiKey: DJSOFGXQESYNSC-UHFFFAOYSA-N

物化性质

• 沸点：
  685.8±65.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 selenium(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 氢溴酸 、 溴 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 生成 4,7-di(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]selenadiazole
  参考文献：
  名称：

  Thieno[3,2-b]thiophene as π-bridge at different acceptor systems for electrochromic applications

  摘要：

  Benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene are the units preferred in conducting polymers due to their electrochemical properties. There are no reports in the literature on polymers containing both moieties. In this study, novel benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene based monomers; 4-(3a,6a-dihydrothieno[3,2-b]thiophen-2-y1)-7-(thieno[3,2-b]thiophenyl) benzo[c][1,2,51selenadiazole (BSeTT) and 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromo-2,3dihydroquinoxaline (QTT) were synthesized via Stille Coupling and polymerized electrochemically. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV Vis NIR spectroscopy. Spectroelectrochemistry analysis of PBSeTT revealed an electronic transition at 525 nm corresponding to pi-pi* transition with a band gap of 0.93 eV whereas PQTT revealed electronic transitions at 440 and 600 nm corresponding to pi-pi*transitions with a band gap of 1.30 eV. Electrochromic investigations showed that PBSeTT has gray color PQTT switching between green and gray. Switching time of the polymers was evaluated by a kinetic study upon measuring the percent transmittance (%T) at the maximum contrast point. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.05.029

文献信息

• Thieno[3,2-b]thiophene as π-bridge at different acceptor systems for electrochromic applications
  作者：Sinem Toksabay、Serife O. Hacioglu、Naime A. Unlu、Ali Cirpan、Levent Toppare

  DOI：10.1016/j.polymer.2014.05.029

  日期：2014.6

  Benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene are the units preferred in conducting polymers due to their electrochemical properties. There are no reports in the literature on polymers containing both moieties. In this study, novel benzoselenadiazole, quinoxaline and thieno[3,2-b]thiophene based monomers; 4-(3a,6a-dihydrothieno[3,2-b]thiophen-2-y1)-7-(thieno[3,2-b]thiophenyl) benzo[c][1,2,51selenadiazole (BSeTT) and 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-dibromo-2,3dihydroquinoxaline (QTT) were synthesized via Stille Coupling and polymerized electrochemically. These polymers were characterized in terms of their spectroelectrochemical and electrochemical properties by cyclic voltammetry and UV Vis NIR spectroscopy. Spectroelectrochemistry analysis of PBSeTT revealed an electronic transition at 525 nm corresponding to pi-pi* transition with a band gap of 0.93 eV whereas PQTT revealed electronic transitions at 440 and 600 nm corresponding to pi-pi*transitions with a band gap of 1.30 eV. Electrochromic investigations showed that PBSeTT has gray color PQTT switching between green and gray. Switching time of the polymers was evaluated by a kinetic study upon measuring the percent transmittance (%T) at the maximum contrast point. (C) 2014 Elsevier Ltd. All rights reserved.