tetrathieno[2,3-a:3',2'-c:2'',3''-f:3''',2'''-h]naphthalene | 1447111-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tetrathieno[2,3-a:3',2'-c:2'',3''-f:3''',2'''-h]naphthalene
• 英文别名: 5,8,16,19-Tetrathiahexacyclo[10.10.0.02,6.07,11.013,17.018,22]docosa-1,3,6,9,11,13(17),14,18(22),20-nonaene；5,8,16,19-tetrathiahexacyclo[10.10.0.02,6.07,11.013,17.018,22]docosa-1,3,6,9,11,13(17),14,18(22),20-nonaene
• CAS: 1447111-40-1
• 化学式: C₁₈H₈S₄
• 分子量: 352.526
• InChiKey: ILTAHKZUJANAHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  6.0
• 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

• 作为产物：
  描述：

  tetra(3-thienyl)ethene 在 碘 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以23%的产率得到tetrathieno[2,3-a:3',2'-c:2'',3''-f:3''',2'''-h]naphthalene
  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.