2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene | 1341199-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene
• 英文别名: Hydroxy-[10-[hydroxy(diphenyl)silyl]-7,7-dimethyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl]-diphenylsilane；hydroxy-[10-[hydroxy(diphenyl)silyl]-7,7-dimethyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl]-diphenylsilane
• CAS: 1341199-10-7
• 化学式: C₃₅H₃₀O₂S₂Si₂
• 分子量: 602.925
• InChiKey: QJROPYMFLGQDAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,6-dibromo-4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene 在 正丁基锂 、 四甲基乙二胺 、 5%-palladium/activated carbon 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 39.5h， 生成 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  Synthesis and properties of cyclopentadithiophene-based poly(silarylenesiloxane) derivatives

  摘要：

  Poly(silarylenesiloxane) derivatives with 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety, bearing dimethyl- (P1), methylphenyl- (P2) and diphenyl- (P3) substituents on silyl moieties, were prepared via polycondensation of the corresponding disilanol monomers, that is, 2,6-bis(dimethylhydroxysilyl)-4,4-dimethylcyclopenta[2,1 -b:3,4-b']dithiophene (M1), 2,6-bis(methylphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M2), and 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M3), respectively. P1 P3 exhibited the good solubility in common organic solvents, such as benzene, toluene, chloroform, dichloromethane, THF, and so on. The glass transition temperatures (T(g)s) of P1, P2 and P3 were determined by differential scanning calorimetry to be 56, 97 and 137 degrees C, respectively, depending on the substituent on the silyl moieties. No melting temperatures (T(m)s) of P1, P2 and P3 were observed, suggesting the obtained P1 P3 are amorphous polymers. The temperatures at 5% weight loss (T(d5)s) of P1, P2 and P3 were 460, 459 and 479 degrees C, respectively, indicating that the larger number of phenyl group on the silyl moieties resulted in the better thermostability. Bathochromic and hyperchromic effects were observed in the absorption and fluorescence spectra by introducing silyl substituents onto 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety. In addition, the bathochromic shift of the maximum absorption (lambda(abs)) and the increase in the fluorescence quantum yield (phi(F)) were observed by the introduction of phenyl group onto the silyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.09.031

文献信息

• Synthesis and properties of cyclopentadithiophene-based poly(silarylenesiloxane) derivatives
  作者：Hitoshi Hanamura、Nobukatsu Nemoto

  DOI：10.1016/j.polymer.2011.09.031

  日期：2011.10

  Poly(silarylenesiloxane) derivatives with 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety, bearing dimethyl- (P1), methylphenyl- (P2) and diphenyl- (P3) substituents on silyl moieties, were prepared via polycondensation of the corresponding disilanol monomers, that is, 2,6-bis(dimethylhydroxysilyl)-4,4-dimethylcyclopenta[2,1 -b:3,4-b']dithiophene (M1), 2,6-bis(methylphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M2), and 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M3), respectively. P1 P3 exhibited the good solubility in common organic solvents, such as benzene, toluene, chloroform, dichloromethane, THF, and so on. The glass transition temperatures (T(g)s) of P1, P2 and P3 were determined by differential scanning calorimetry to be 56, 97 and 137 degrees C, respectively, depending on the substituent on the silyl moieties. No melting temperatures (T(m)s) of P1, P2 and P3 were observed, suggesting the obtained P1 P3 are amorphous polymers. The temperatures at 5% weight loss (T(d5)s) of P1, P2 and P3 were 460, 459 and 479 degrees C, respectively, indicating that the larger number of phenyl group on the silyl moieties resulted in the better thermostability. Bathochromic and hyperchromic effects were observed in the absorption and fluorescence spectra by introducing silyl substituents onto 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety. In addition, the bathochromic shift of the maximum absorption (lambda(abs)) and the increase in the fluorescence quantum yield (phi(F)) were observed by the introduction of phenyl group onto the silyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.