5-bromo-5'-ethynyl-3,3'-dihexyl-2,2'-bithiophene | 609771-55-3

• 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: 5-bromo-5'-ethynyl-3,3'-dihexyl-2,2'-bithiophene
• 英文别名: 2-(5-Bromo-3-hexylthiophen-2-yl)-5-ethynyl-3-hexylthiophene
• CAS: 609771-55-3
• 化学式: C₂₂H₂₉BrS₂
• 分子量: 437.508
• InChiKey: JIIPAAMRKAAYKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-5'-ethynyl-3,3'-dihexyl-2,2'-bithiophene 、 5-ethynyl-2,3,7,8,12,13,17,18-octaethylporphyrinatonickel(II) 在 copper diacetate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 5-bromo-5'-{4-[2,3,7,8,12,13,17,18-octaethylporphyrinatonickel(II)-5-yl]-1,3-butadiynyl}-3,3'-dihexyl-2,2'-bithiophene 、 meso,meso'-bis(octaethylporphyrinyl)butadiyne, dinickel complex
  参考文献：
  名称：

  Orientation and Substituent Effects on the Properties of the Diacetylene-Group Connected Octaethylporphyrin–Dihexylbithiophene Derivatives (OEP–DHBTh–X) Carrying Electron-Withdrawing Groups

  摘要：

  合成了连接有二炔基链的八乙基卟啉-二己基二噻苯（OEP-DHBTh）异构体，末端附有不同的电子吸引取代基X。研究了DHBTh方向和X取代基对OEP-DHBTh-X（X = H, Br, CN, CHO和NO2）性质的影响，并与相关OEP衍生物进行了比较。

  DOI：

  10.1246/bcsj.80.371
• 作为产物：
  描述：

  5,5'-二溴-3,3'-二己基-2,2'-并噻吩 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium carbonate 、 二异丙胺 作用下， 以 甲醇 、 正己烷 为溶剂， 生成 5-bromo-5'-ethynyl-3,3'-dihexyl-2,2'-bithiophene
  参考文献：
  名称：

  Orientation and Substituent Effects on the Properties of the Diacetylene-Group Connected Octaethylporphyrin–Dihexylbithiophene Derivatives (OEP–DHBTh–X) Carrying Electron-Withdrawing Groups

  摘要：

  合成了连接有二炔基链的八乙基卟啉-二己基二噻苯（OEP-DHBTh）异构体，末端附有不同的电子吸引取代基X。研究了DHBTh方向和X取代基对OEP-DHBTh-X（X = H, Br, CN, CHO和NO2）性质的影响，并与相关OEP衍生物进行了比较。

  DOI：

  10.1246/bcsj.80.371

文献信息

• Syntheses and electronic properties of the nickel and palladium complexes of the octaethylporphyrin(M1)–(dihexylbithiophene) n –octaethylporphyrin(M2) system [OEP(M1)–(DHBTh) n –OEP(M2)] connected with the diacetylene linkage. A methodology for molecular design of the particular electronic structure
  作者：Naoto Hayashi、Miho Murayama、Kazumine Mori、Akihito Matsuda、Emiko Chikamatsu、Keita Tani、Keiko Miyabayashi、Mikio Miyake、Hiroyuki Higuchi

  DOI：10.1016/j.tet.2004.04.064

  日期：2004.7

  The palladium complexes of highly extended pi-electronic conjugation system, octaethyl porphyrin (Pd)-(dihexylbithiophene)(n)-octaethylporphyrin(Pd) [OEP(Pd)-(DHBTh)(n)-OEP(Pd), n=1-6], were synthesized, in which all the chromophores are connected with diacetylene linkage. The unsymmetrical derivatives of OEP(Ni)-DHBTh-OEP(Pd) were also successfully synthesized. Electronic properties of these symmetrical and unsymmetrical complexes were conclusively described, as compared with those of OEP(Ni)(DHBTh)(n)-OEP(Ni). Based on the structure elements, a methodical guiding principle for molecular design of the particular electronic structure will be proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and properties of unsymmetrically extended π-electronic conjugation system of octaethylporphyrin(Ni)–dihexybithiophene–octaethylporphyrin(Pd) connected with diacetylene linkage
  作者：Naoto Hayashi、Akihito Matsuda、Emiko Chikamatsu、Kazumine Mori、Hiroyuki Higuchi

  DOI：10.1016/s0040-4039(03)01839-2

  日期：2003.9

  Orientational isomers of the diacetylene-group connected dihexybithiophene (DHBTh) derivatives have been synthesized. in which the different octaethylporphyrin (OEP(M): M=Ni or Pd) rings are attached at the ends. Reflecting the unsymmetrical structural feature, the peculiar electronic properties of the extended OEP(Ni)-DHBTh-OEP(Pd) system were observed. (C) 2003 Elsevier Ltd. All rights reserved.