(5-bromo-3-hexylthiophen-2-yl)magnesium chloride | 1196663-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (5-bromo-3-hexylthiophen-2-yl)magnesium chloride
• CAS: 1196663-02-1
• 化学式: C₁₀H₁₄BrClMgS
• 分子量: 305.949
• InChiKey: ZZBZIIVHCSISJY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (5-bromo-3-hexylthiophen-2-yl)magnesium chloride 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 lithium chloride 、 盐酸 作用下， 以 水 为溶剂， 生成 2-溴-4-己基噻吩
  参考文献：
  名称：

  LiCl-Promoted Chain Growth Kumada Catalyst-Transfer Polycondensation of the “Reversed” Thiophene Monomer

  摘要：

  The effect of LiCl on the chain growth Kumada catalyst-transfer polycondensation (KCTP) of the "reversed" thiophene monomer, 5-bromo-2-chloromagnesio-3-hexylthiophene (3a) (that has bulky substituent adjacent to the chloromagnesium group), was investigated. LiCl promotes the polymerization of 3a, and the polymerization also exhibits living characteristics similar to those of the "normal" monomer, 2-bromo-5-chloromagnesio-3-heacylthiophene (3b). However, initiation is much slower than chain propagation due to the steric hindrance between hexyl groups in the transmetalation (TM) step that leads to the formation of the initiator via head-to-head (HH) coupling. Consequently, regioregular poly(3-hexylthiophene) (P3HT) with large polydispersity (PDI) and higher number-average molecular weight (M-n) than the theoretical value was obtained. Because of the slow initiation with 3a, the polymerization of 3a occurs primarily after the consumption of 3b in the copolymerization of 3a and 3b, and P3HT with high regioregularity was still obtained.

  DOI：

  10.1021/ma201192p

文献信息

• LIVING SYNTHESIS OF CONDUCTING POLYMERS INCLUDING REGIOREGULAR POLYMERS, POLYTHIOPHENES, AND BLOCK COPOLYMERS
  申请人：CARNEGIE MELLON UNIVERSITY

  公开号：EP1872405B1

  公开（公告）日：2016-02-03
• Living synthesis of conducting polymers including regioregular polymers, polythiophenes, and block copolymers
  申请人：McCullough D. Richard

  公开号：US20060278867A1

  公开（公告）日：2006-12-14

  Regioregular poly(3-alkylthiophenes) and other polythiophenes can be prepared by living polymerization which have good solubility, processability and environmental stability. The polymerization method can afford regioregular poly(3-alkylthiophenes) in high yields. Kinetic study of polymerization revealed the living character of this process. The molecular weight of poly(3-alkylthiophenes) is a function of the molar ratio of the monomer to nickel initiator, and conducting polymers with relatively narrow molecular weight distribution (PDI<1.5) are now readily available. Sequential monomer addition resulted in new block copolymers containing different poly(3-alkylthiophene) segments, which further confirms the “livingness” of this system. Other synthetic methods can be used as well to conduct living polymerization. Blends and electronic devices can be prepared.
• PHOTOELECTRIC CONVERSION ELEMENT AND MANUFACTURING METHOD THEREOF
  申请人：ASAHI GLASS COMPANY, LIMITED

  公开号：US20140130871A1

  公开（公告）日：2014-05-15

  There are provided a photoelectric conversion element with high photoelectric conversion efficiency, whose light absorption efficiency, charge separation efficiency, and charge transport efficiency are at high level, and a method for efficiently manufacturing the photoelectric conversion element. A photoelectric conversion element has an anode, a cathode opposed to the anode, and an organic film disposed between the anode and the cathode and containing a liquid-crystalline conjugated block polymer. A method of manufacturing the above mentioned photoelectric conversion element has the step of, (1) preparing an organic film forming composition containing the liquid-crystalline conjugated block polymer; (2) forming the one electrode and a coating film using the composition on it; (3) heat treating the coating film within a temperature range in a liquid-crystalline state so as to obtain an organic film; and (4) forming the other electrode which is not formed in the step (2) above the organic film.
• US7452958B2
  申请人：——

  公开号：US7452958B2

  公开（公告）日：2008-11-18
• US7834106B2
  申请人：——

  公开号：US7834106B2

  公开（公告）日：2010-11-16