2-Thiophen-2-yl-5-[13-(5-thiophen-2-ylthiophen-2-yl)-5,14-dihydropentacen-6-yl]thiophene | 1333867-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 2-Thiophen-2-yl-5-[13-(5-thiophen-2-ylthiophen-2-yl)-5,14-dihydropentacen-6-yl]thiophene
• 英文别名: 2-thiophen-2-yl-5-[13-(5-thiophen-2-ylthiophen-2-yl)-5,14-dihydropentacen-6-yl]thiophene
• CAS: 1333867-51-8
• 化学式: C₃₈H₂₄S₄
• 分子量: 608.873
• InChiKey: KWHKFVWRSGAXJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-Thiophen-2-yl-5-[13-(5-thiophen-2-ylthiophen-2-yl)-5,14-dihydropentacen-6-yl]thiophene 在 γ-松油烯 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 6,13-di(5,2'-bithiophen-2-yl)pentacene
  参考文献：
  名称：

  Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene

  摘要：

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

  DOI：

  10.3987/com-12-s(n)130
• 作为产物：
  描述：

  6,13-bis(trimethylsilyl)-5,14-dihydropentacene 在 四(三苯基膦)钯 、 一氯化碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-Thiophen-2-yl-5-[13-(5-thiophen-2-ylthiophen-2-yl)-5,14-dihydropentacen-6-yl]thiophene
  参考文献：
  名称：

  Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene

  摘要：

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.

  DOI：

  10.3987/com-12-s(n)130

文献信息

• Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene
  作者：Tamotsu Takahashi、Zhiying Jia、Shi Li、Kiyohiko Nakajima、Ken-ichiro Kanno、Zhiyi Song

  DOI：10.3987/com-12-s(n)130

  日期：——

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.