5-bromo-5'-ethyl-2,2'-bithiophene | 851604-87-0

• 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-bromo-5'-ethyl-2,2'-bithiophene
• 英文别名: 2-Bromo-5-(5-ethylthiophen-2-yl)thiophene
• CAS: 851604-87-0
• 化学式: C₁₀H₉BrS₂
• 分子量: 273.217
• InChiKey: LKPLZFILCIETFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-2-[5'-(10-undecenyl)-2,2'-bithiene-5-yl]-1,3,2-dioxarbolane 、 5-bromo-5'-ethyl-2,2'-bithiophene 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 20.0h， 以68%的产率得到5-ethyl-5'''-(10-undecenyl)-2,2':5',2'':5'',2'''-quaterthiophene
  参考文献：
  名称：

  Unsymmetrische lineare organische Oligomere

  摘要：

  公开号：

  EP1531155B1
• 作为产物：
  描述：

  5-Aethyl-2,2'-bithiophen 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到5-bromo-5'-ethyl-2,2'-bithiophene
  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

• 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。
• Halbleitende Schichten enthaltend lineare organische Thiophen-Phenylen-Oligomere
  申请人：H.C. Starck GmbH

  公开号：EP1867651A1

  公开（公告）日：2007-12-19

  Die Erfindung betrifft neue halbleitende Schichten enthaltend lineare organische Thiophen-Phenylen-Oitgomere der allgemeinen Formel (I) wobei die Verbindungen gemäß Formel (I) unter Verwendung von Thiophen-Pinakoilnboronsäureestern hergestellt werden.

  本发明涉及含有通式(I)的线性有机噻吩-苯基邻构体的新型半导体层 其中，根据式（I）的化合物是用噻吩-联苯硼酸酯制备的。
• Asymmetrical linear organic oligomers
  申请人：Kirchmeyer Stephan

  公开号：US20050139822A1

  公开（公告）日：2005-06-30

  The invention relates to asymmetrical linear organic oligomers represented by the following formula (I), X—R 1 —[—Ar—] n —R 2 (I) in which n is from 4 to 10, Ar is for example an optionally substituted 2,5-thienylene group, R 1 is for example a C 10 -C 20 alkylene group, R 2 is for example a C 1 -C 12 alkyl group, and X is for example a vinyl group or an alkoxysilyl group. Also described is a process for the production of such organic oligomers, and semiconductors in electronic modules that include such organic oligomers.

  本发明涉及下式(I)所代表的不对称线性有机低聚物、 X-R 1 -[-Ar-]-[-Ar-] n -R 2 (I) 其中 n 为 4 至 10，Ar 例如为任选取代的 2,5-噻吩基团，R 1 例如是一个 C 10 -C 20 烯基，R 2 例如是 C 1 -C 12 烷基，X 是乙烯基或烷氧基硅基。此外，还介绍了生产这种有机低聚物的工艺，以及包括这种有机低聚物的电子模块中的半导体。
• Applications of Silicon-Bridged Oligothiophenes to Organic FET Materials
  作者：Joji Ohshita、Yuki Izumi、Dong-Ha Kim、Atsutaka Kunai、Takao Kosuge、Yoshihito Kunugi、Akinobu Naka、Mitsuo Ishikawa

  DOI：10.1021/om700631s

  日期：2007.12.1

  Trisilanylene-bridged oligothiophenes were synthesized, and their vapor-deposited and spin-coated films were examined as p-type semiconductors in field-effect transistors (FET). Of these, the best FET performance was achieved by using tris[(ethylquinquethiophenyl)dimethylsilyl]methylsilane as the active material, whose field-effect mobility and on/off ratio were determined to be 6.4 x 10(-2) cm(2) V-1 s(-1) and 10(4), respectively. Interestingly, the trisilanylene-bridged oligothiophenes were found to be photoactive and the FET activity of the films was suppressed, when irradiated in air (254 nm), being potentially usable as patternable FET materials.
• Verfahren zur Herstellung linearer organischer Thiophen-Phenylen-Oligomere
  申请人：H.C. Starck Clevios GmbH

  公开号：EP1531154B1

  公开（公告）日：2010-04-14