tetra(3-thienyl)ethene | 1447111-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tetra(3-thienyl)ethene
• 英文别名: 3-[1,2,2-Tri(thiophen-3-yl)ethenyl]thiophene；3-[1,2,2-tri(thiophen-3-yl)ethenyl]thiophene
• CAS: 1447111-33-2
• 化学式: C₁₈H₁₂S₄
• 分子量: 356.557
• InChiKey: NLLBUUUMDAXWMG-UHFFFAOYSA-N

物化性质

• 沸点：
  434.3±40.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetra(3-thienyl)ethene 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以41%的产率得到5,6-di(3-thienyl)dithieno[2,3-a:3',2'-c]benzene
  参考文献：
  名称：

  Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c:2″,3″-f:3‴,2‴-h]naphthalene: a new π-conjugated system obtained by photoinduced electrocyclization–dehydrogenation reactions of tetra(3-thienyl)ethene

  摘要：

  method for the synthesis of tetrathieno[2,3-a:3',2'-c:2 '',3 ''-f:3''',2'''-h]naphthalene (3), utilizing photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene (1), was developed. Photoirradiation of a toluene or CHCl3 solution of 1, containing a small amount of I-2, leads to modestly efficient production of 3. In contrast to the UV-vis absorption property of the typical p-type organic transistor material pentacene, that of 3 does not experience a time-dependent change under aerated conditions, indicating that 3 has high stability against molecular oxygen. The results of X-ray crystallographic analysis demonstrate that 3 possesses a columnar crystalline structure in which molecules are aligned in a face-to-face manner with a high degree of the TE-TE overlap between adjacent molecules. This phenomenon should result in efficient charge-carrier transport properties of the crystalline form of this substance. C 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.090
• 作为产物：
  描述：

  di(thiophen-3-yl)methanone 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以3.69 g的产率得到tetra(3-thienyl)ethene
  参考文献：
  名称：

  Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c:2″,3″-f:3‴,2‴-h]naphthalene: a new π-conjugated system obtained by photoinduced electrocyclization–dehydrogenation reactions of tetra(3-thienyl)ethene

  摘要：

  method for the synthesis of tetrathieno[2,3-a:3',2'-c:2 '',3 ''-f:3''',2'''-h]naphthalene (3), utilizing photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene (1), was developed. Photoirradiation of a toluene or CHCl3 solution of 1, containing a small amount of I-2, leads to modestly efficient production of 3. In contrast to the UV-vis absorption property of the typical p-type organic transistor material pentacene, that of 3 does not experience a time-dependent change under aerated conditions, indicating that 3 has high stability against molecular oxygen. The results of X-ray crystallographic analysis demonstrate that 3 possesses a columnar crystalline structure in which molecules are aligned in a face-to-face manner with a high degree of the TE-TE overlap between adjacent molecules. This phenomenon should result in efficient charge-carrier transport properties of the crystalline form of this substance. C 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.090

文献信息

• Synthesis and basic properties of tetrathieno[2,3-a:3′,2′-c:2″,3″-f:3‴,2‴-h]naphthalene: a new π-conjugated system obtained by photoinduced electrocyclization–dehydrogenation reactions of tetra(3-thienyl)ethene
  作者：Atsushi Yamamoto、Eisuke Ohta、Nao Kishigami、Norihiro Tsukahara、Yusuke Tomiyori、Hiroyasu Sato、Yasunori Matsui、Yusuke Kano、Kazuhiko Mizuno、Hiroshi Ikeda

  DOI：10.1016/j.tetlet.2013.05.090

  日期：2013.7

  method for the synthesis of tetrathieno[2,3-a:3',2'-c:2 '',3 ''-f:3''',2'''-h]naphthalene (3), utilizing photoinduced electrocyclization-dehydrogenation reactions of tetra(3-thienyl)ethene (1), was developed. Photoirradiation of a toluene or CHCl3 solution of 1, containing a small amount of I-2, leads to modestly efficient production of 3. In contrast to the UV-vis absorption property of the typical p-type organic transistor material pentacene, that of 3 does not experience a time-dependent change under aerated conditions, indicating that 3 has high stability against molecular oxygen. The results of X-ray crystallographic analysis demonstrate that 3 possesses a columnar crystalline structure in which molecules are aligned in a face-to-face manner with a high degree of the TE-TE overlap between adjacent molecules. This phenomenon should result in efficient charge-carrier transport properties of the crystalline form of this substance. C 2013 Elsevier Ltd. All rights reserved.