[(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-19-[4-[5-[(1Z,6Z,11Z,16Z)-9,14,19-tris(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]thiophen-3-yl]thiophen-2-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane | 1520923-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: [(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-19-[4-[5-[(1Z,6Z,11Z,16Z)-9,14,19-tris(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]thiophen-3-yl]thiophen-2-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane
• CAS: 1520923-65-2
• 化学式: C₅₈H₆₆S₁₀Si₆
• 分子量: 1252.34
• InChiKey: INRYCNARLUOQPR-QRXJANSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.54
• 重原子数：
  74
• 可旋转键数：
  9
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  259
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-19-[4-[5-[(1Z,6Z,11Z,16Z)-9,14,19-tris(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]thiophen-3-yl]thiophen-2-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane 在 正丁基锂 、 copper dichloride 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 35.0h， 以30%的产率得到[(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-19-[(1Z,6Z,11Z,16Z)-9,14,19-tris[(1Z,6Z,11Z,16Z)-9,14,19-tris(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane
  参考文献：
  名称：

  Derivation of saddle shaped cyclooctatetrathiophene: increasing conjugation and fabricating pentamer

  摘要：

  With cyclooctatetrathiophene (COTh) as building block, two alpha,alpha,alpha,alpha-tetraaryl COThs, COThP and COThTh have been efficiently synthesized. Phenyl and thienyl were employed as end-capping groups to introduce to COTh and increase its conjugation. For enlarging the special 'saddle' shaped structure, a pentamer of COTh was synthesized via Negishi reaction and CuCl2-promoted oxidative coupling reaction. The pentamer (COThF) is a new type of dendrimer with COTh as dendron, which presents an artistic configuration possessing a large saddle shape. All compounds were fully characterized by H-1 NMR, C-13 NMR, HRMS and IR. The crystal structures of COThP and COThTh were confirmed by X-ray analysis. The molecular configuration of COThF was optimized by theoretical calculations. Their UV-vis properties, electrochemical behaviours and thermo-gravimetric analysis of COThP, COThTh and COThF were also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.002
• 作为产物：
  描述：

  5,5'-dibromo-3,3'-bithiophene 、 [(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane 在 正丁基锂 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 76.5h， 以67%的产率得到[(1Z,6Z,11Z,16Z)-9,14-bis(trimethylsilyl)-19-[4-[5-[(1Z,6Z,11Z,16Z)-9,14,19-tris(trimethylsilyl)-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]thiophen-3-yl]thiophen-2-yl]-3,10,13,20-tetrathiapentacyclo[15.3.0.02,6.07,11.012,16]icosa-1,4,6,8,11,14,16,18-octaen-4-yl]-trimethylsilane
  参考文献：
  名称：

  Derivation of saddle shaped cyclooctatetrathiophene: increasing conjugation and fabricating pentamer

  摘要：

  With cyclooctatetrathiophene (COTh) as building block, two alpha,alpha,alpha,alpha-tetraaryl COThs, COThP and COThTh have been efficiently synthesized. Phenyl and thienyl were employed as end-capping groups to introduce to COTh and increase its conjugation. For enlarging the special 'saddle' shaped structure, a pentamer of COTh was synthesized via Negishi reaction and CuCl2-promoted oxidative coupling reaction. The pentamer (COThF) is a new type of dendrimer with COTh as dendron, which presents an artistic configuration possessing a large saddle shape. All compounds were fully characterized by H-1 NMR, C-13 NMR, HRMS and IR. The crystal structures of COThP and COThTh were confirmed by X-ray analysis. The molecular configuration of COThF was optimized by theoretical calculations. Their UV-vis properties, electrochemical behaviours and thermo-gravimetric analysis of COThP, COThTh and COThF were also described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.002

文献信息

• Derivation of saddle shaped cyclooctatetrathiophene: increasing conjugation and fabricating pentamer
  作者：Yong Wang、Dewen Gao、Jianwu Shi、Yuhe Kan、Jinsheng Song、Chunli Li、Hua Wang

  DOI：10.1016/j.tet.2013.12.002

  日期：2014.1

  With cyclooctatetrathiophene (COTh) as building block, two alpha,alpha,alpha,alpha-tetraaryl COThs, COThP and COThTh have been efficiently synthesized. Phenyl and thienyl were employed as end-capping groups to introduce to COTh and increase its conjugation. For enlarging the special 'saddle' shaped structure, a pentamer of COTh was synthesized via Negishi reaction and CuCl2-promoted oxidative coupling reaction. The pentamer (COThF) is a new type of dendrimer with COTh as dendron, which presents an artistic configuration possessing a large saddle shape. All compounds were fully characterized by H-1 NMR, C-13 NMR, HRMS and IR. The crystal structures of COThP and COThTh were confirmed by X-ray analysis. The molecular configuration of COThF was optimized by theoretical calculations. Their UV-vis properties, electrochemical behaviours and thermo-gravimetric analysis of COThP, COThTh and COThF were also described. (C) 2013 Elsevier Ltd. All rights reserved.