4,8-di(thien-3-yl)thieno[2,3-g:5,4-g']bis[1]benzothiophene | 1619917-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 4,8-di(thien-3-yl)thieno[2,3-g:5,4-g']bis[1]benzothiophene
• 英文别名: 8,14-Di(thiophen-3-yl)-4,11,18-trithiapentacyclo[10.7.0.02,10.03,7.015,19]nonadeca-1(12),2(10),3(7),5,8,13,15(19),16-octaene；8,14-di(thiophen-3-yl)-4,11,18-trithiapentacyclo[10.7.0.02,10.03,7.015,19]nonadeca-1(12),2(10),3(7),5,8,13,15(19),16-octaene
• CAS: 1619917-16-6
• 化学式: C₂₄H₁₂S₅
• 分子量: 460.689
• InChiKey: DVVFFGMNOHKIJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-bis[2,2-di(thien-3-yl)ethenyl]thiophene 在 四氯苯醌 作用下， 以 氘代氯仿 为溶剂， 以93%的产率得到4,8-di(thien-3-yl)thieno[2,3-g:5,4-g']bis[1]benzothiophene
  参考文献：
  名称：

  One-pot photochemical synthesis of novel thienobis[1]benzothiophene with an angularly-fused structure that promotes unique intermolecular S⋯S contacts in the crystalline state

  摘要：

  4,8-Di(thien-3-yl)thieno[2,3-g:5,4-g']bis[1]benzothiophene (8a), a member of a new class of angularly-fused thienobis[1]benzothiophenes (TBBTs), was synthesized by using a one-pot photocyclization-dehydrogenation reaction of 2,5-bis[2,2-di(thien-3-yl)ethenyl]thiophene (7a). The results of absorption and emission spectroscopy, and cyclic voltammetry studies suggest that the effective conjugation length of 8a is shorter than that of 7a. X-ray crystallographic analysis revealed that the core TBBT framework of 8a is slightly twisted. In the crystalline state, molecules of 8a are arranged in stacked columns that interact with the adjacent stacked columns via S...S contacts. Moreover, a 1:1 charge-transfer complex between 8a and 7,7,8,8-tetracyanoquinodimethane (TCNQ) forms crystals that have an alternating stacked columnar structure with both 8a and TCNQ being aligned in individual ribbon-like motifs. The crystal properties of these substances suggest that the angularly-fused TBBT framework might be a useful platform for the construction of electrically interesting materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.096