5,8,11,14-tetrathia<9>helicene | 174814-07-4

• 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: 5,8,11,14-tetrathia<9>helicene
• 英文别名: tetrathia[9]helicene；TTH；5,8,11,14-tetrathia[9]helicene；11,16,21,26-Tetrathianonacyclo[18.14.0.02,17.03,15.04,12.05,10.022,34.025,33.027,32]tetratriaconta-1(20),2(17),3(15),4(12),5,7,9,13,18,22(34),23,25(33),27,29,31-pentadecaene
• CAS: 174814-07-4
• 化学式: C₃₀H₁₄S₄
• 分子量: 502.705
• InChiKey: BJVSWSLLKKRZFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  9.0
• 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：

  7,7,8,8-四氰基对苯二醌二甲烷 、 5,8,11,14-tetrathia<9>helicene 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Thiaheterohelicenes. 3. Donor Properties of a Series of Benzene-Capped Thiaheterohelicenes. Structure of a Tetrathianonahelicene and its TCNQ Salt.

  摘要：

  The donor properties of a series of thiaheterohelicenes have been investigated by cyclic voltammetry. The thiaheterohelicenes are oxidised to the corresponding cation radicals at potentials from 1.03 to 1.45 V vs. SCE. The structure of racemic 5,8,11,14-tetrathia[9]helicene 1 was solved. Compound 1 crystallizes in the orthorhombic system, space group Pbca, with a=8.304(2), b=15.842(3), c=33.400(8) Angstrom, V=4394(2) Angstrom(3). Compound 1 can be oxidised to a rather unstable semiconducting salt, (1)(2)PF6. Treatment of racemic 1 with 7,7',8,8'-tetracyanoquinodimethane (TCNQ) gave an insulating solid, 1:TCNQ. The structure of 1:TCNQ was solved. 1:TCNQ crystallizes in the monoclinic system space group C2/c, with a=20.049(5), b=15.258(3), c=10.960(1) Angstrom, beta=103.78(2)degrees, V=3256(1) Angstrom(3). The compound crystallizes in a so-called mixed stack structure.

  DOI：

  10.3891/acta.chem.scand.50-0083
• 作为产物：
  描述：

  1,2-bis(thieno<3,2-a>dibenzothiophen-2-yl)ethene 在 air 、 碘 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以55%的产率得到5,8,11,14-tetrathia<9>helicene
  参考文献：
  名称：

  Thiaheterohelicenes. 1. Synthesis of Unsubstituted Thia[5]-, [9]- and [13]heterohelicenes.

  摘要：

  The unsubstituted thiaheterohelicenes, 5,8-dithia[5]helicene, 1, 5,8,11,14-tetrathia[9]helicene, 2, and 5,8,11, 14,17,20-hexathia[13]helicene, 3, have been prepared. The key reaction was the oxidative photolysis of 1,2-diaryl-substituted ethenes which were prepared by Wittig-Horner or McMurry reactions.

  DOI：

  10.3891/acta.chem.scand.50-0071