6,6'-(2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)-1,4-phenylene)bis(3-bromopyridine) | 1201908-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,6'-(2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)-1,4-phenylene)bis(3-bromopyridine)
• 英文别名: 1,4-bis[2-(5-bromopyridyl)]-2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)benzene；2-[2,5-Bis(5-bromopyridin-2-yl)-4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]ethoxy-tert-butyl-dimethylsilane
• CAS: 1201908-86-2
• 化学式: C₃₂H₄₆Br₂N₂O₂Si₂
• 分子量: 706.708
• InChiKey: ZVVLDCDGCIXULI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.46
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6'-(2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)-1,4-phenylene)bis(3-bromopyridine) 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到
  参考文献：
  名称：

  Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers

  摘要：

  Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C(60) based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.

  DOI：

  10.1021/ja906513u
• 作为产物：
  描述：

  2,5-二溴吡啶 、 (2,2'-(2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-phenylene)bis(ethane-2,1-diyl))bis(oxy)bis(tert-butyldimethylsilane) 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 24.0h， 以58%的产率得到6,6'-(2,5-bis(2-(tert-butyldimethylsilyloxy)ethyl)-1,4-phenylene)bis(3-bromopyridine)
  参考文献：
  名称：

  Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers

  摘要：

  Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C(60) based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.

  DOI：

  10.1021/ja906513u

文献信息

• Poly(3-hexylthiophene)-<i>block</i>-poly(pyridinium phenylene)s: Block Polymers of p- and n-Type Semiconductors
  作者：Daisuke Izuhara、Timothy M. Swager

  DOI：10.1021/ma102566u

  日期：2011.4.26

  Conjugated crystalline-crystalline donor- acceptor-donor block copolymer semiconductors, with regio-regular poly(3-hexylthiophene) as a donor (p-type) block and poly(pyridinium pheneylene) as an acceptor (n-type) block within the backbone, were produced by sequential Grignard metathesis synthesis of poly(3-hexylthiophene), a Yamamoto-type cross-coupling polymerization-cyclization sequence. These conjugated block copolymers are soluble in organic solvents and display broad optical absorption bands extending close to the near-infrared region. They show reversible ambipolar redox properties with high electron affinities of 3.8-4.0 eV as well as useful ionization potentials of 5.1 eV that are characteristic of the respective blocks. Block copolymers from p- and n-type organic semiconductors are of interest for the formation of nanostructured bulk heterojunctions in photovoltaic devices.
• Poly(Pyridinium Phenylene)s: Water-Soluble N-Type Polymers
  作者：Daisuke Izuhara、Timothy M. Swager

  DOI：10.1021/ja906513u

  日期：2009.12.16

  Poly(pyridinium phenylene) conjugated polymers are synthesized by a cross-coupling and cyclization sequence. These polyelectrolytes are freely soluble in water and display high degrees of electroactivity. When reduced (n-doped) these materials display in situ conductivities as high as 160 S/cm. The high conductivity is attributed to the planar structure that is enforced by the cyclic structures of the polymer. The electron affinities are compared to PCBM, a C(60) based n-type material. We find that these polymers undergo excited state electron transfer reactions with other donor conjugated polymers and hence may find utility in photovoltaic devices.