5-hexyl-5''''-(5-hexenyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene | 1245732-86-8

• 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-hexyl-5''''-(5-hexenyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
• 英文别名: 2-[5-(5-Hex-5-enylthiophen-2-yl)thiophen-2-yl]-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene；2-[5-(5-hex-5-enylthiophen-2-yl)thiophen-2-yl]-5-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 1245732-86-8
• 化学式: C₃₂H₃₄S₅
• 分子量: 578.952
• InChiKey: CQPSOKWHWBAJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二甲基一氯硅烷 、 5-hexyl-5''''-(5-hexenyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene 在 Carsted catalyst 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以93%的产率得到chloro[6-(5''''-hexyl-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene-5-yl)hexyl] dimethylsilane
  参考文献：
  名称：

  Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors

  摘要：

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).

  DOI：

  10.1021/om100139y
• 作为产物：
  描述：

  4,4,5,5-tetramethyl-2-[5''-(5-hexenyl)-2,2':5',2''-terthiene-5-yl]-1,3,2-dioxaborolane 、 5-溴-5′-己基-2,2′-联噻吩 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以57%的产率得到5-hexyl-5''''-(5-hexenyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
  参考文献：
  名称：

  Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors

  摘要：

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).

  DOI：

  10.1021/om100139y

文献信息

• Synthesis of Monochlorosilyl Derivatives of Dialkyloligothiophenes for Self-Assembling Monolayer Field-Effect Transistors
  作者：Sergei A. Ponomarenko、Oleg V. Borshchev、Timo Meyer-Friedrichsen、Alexandra P. Pleshkova、Sepas Setayesh、Edsger C. P. Smits、Simon G. J. Mathijssen、Dago M. de Leeuw、Stephan Kirchmeyer、Aziz M. Muzafarov

  DOI：10.1021/om100139y

  日期：2010.10.11

  Unsymmetrical dimethylchlorosilyl-substituted alpha,alpha'-dialkylquater-, quinque-, and sexithiophenes were designed and successfully synthesized by a combination of Kumada and Suzuki cross-coupling reactions followed by hydrosilylation. Optimization possibilities of the hydrosilylation of low-soluble linear oligothiophenes by dimethylchlorosilane as well as the nonreactive byproducts formed are described. The molecular structures of the obtained dimethylchlorosilyl-functionalized oligothiophenes were proven by NMR and DCI MS techniques. These compounds were found to be stable and reactive enough, even in the presence of the nonreactive byproducts, to form semiconducting monolayers on dielectric hydroxylated SiO2 surfaces by self-assembly from solution. The semiconducting properties of these oligothiophene SAMs were as good as those of bulk oligothiophenes. This allowed the production of stable, even under ambient conditions, SAMFETs with a mobility of up to 0.04 cm(2)/(V s) and an on/off ratio up to 1 x 10(8).