4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxarbolane | 851298-62-9

• 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: 4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxarbolane
• 英文别名: 4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithien-5-yl]-1,3,2-dioxaborolane；4,4,5,5-Tetramethyl-2-[5-(5-undec-10-enylthiophen-2-yl)thiophen-2-yl]-1,3,2-dioxaborolane
• CAS: 851298-62-9
• 化学式: C₂₅H₃₇BO₂S₂
• 分子量: 444.511
• InChiKey: UHVSPXOLYCPFPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethyl-5''-bromo-2,2':5',2''-terthiophene 、 4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxarbolane 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 以83%的产率得到5-ethyl-5''''-(10-undecenyl)-2,2':5',2'':5'',2''':5''',2''''-quinoquethiophene
  参考文献：
  名称：

  Unsymmetrische lineare organische Oligomere

  摘要：

  公开号：

  EP1531155B1
• 作为产物：
  描述：

  5-undec-10-en-1-yl-2,2’-bithiophene 、 异丙醇频哪醇硼酸酯 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.0h， 以97%的产率得到4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxarbolane
  参考文献：
  名称：

  Process for the production of linear organic thiophene-phenylene oligomers

  摘要：

  本发明涉及一种新型的线性有机噻吩-苯基寡聚物的生产方法，该寡聚物由以下通式（I）表示。该方法涉及将以下通式（II）所表示的化合物通过Suzuki偶联反应等反应与以下通式（III）所表示的化合物反应，其中YArmY  （III）。该反应可以在催化剂的存在下、在溶液中或在高温下进行。本发明的线性有机噻吩-苯基寡聚物可用于形成半导体涂层。

  公开号：

  US20050098777A1

文献信息

• Process for the production of linear organic thiophene-phenylene oligomers
  申请人：Kirchmeyer Stephan

  公开号：US20050098777A1

  公开（公告）日：2005-05-12

  The invention relates to a novel process for the production of linear organic thiophene-phenylene oligomers represented by the following general formula (I), The process involves reacting (e.g., by means of a Suzuki coupling reaction) a compound represented by the following general formula (II), with a formula represented by the following general formula (III), YAr m Y   (III) The reaction may be conducted optionally in the presence of catalysts, optionally in a solution and/or optionally at elevated temperature. The linear organic thiophene-phenylene oligomers of the present invention may be used to form semi-conductive coatings.

  本发明涉及一种新型的线性有机噻吩-苯基寡聚物的生产方法，该寡聚物由以下通式（I）表示。该方法涉及将以下通式（II）所表示的化合物通过Suzuki偶联反应等反应与以下通式（III）所表示的化合物反应，其中YArmY  （III）。该反应可以在催化剂的存在下、在溶液中或在高温下进行。本发明的线性有机噻吩-苯基寡聚物可用于形成半导体涂层。
• Unsymmetrische lineare organische Oligomere
  申请人：H.C. Starck GmbH & Co. KG

  公开号：EP1531155B1

  公开（公告）日：2007-08-01
• 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).