5-ethyl-5''-bromo-2,2':5',2''-terthiophene | 349147-66-6

• 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-ethyl-5''-bromo-2,2':5',2''-terthiophene
• 英文别名: 5-bromo-5''-ethyl-2,2':5',2''-terthiophene；5-bromo-5''-ethylterthiophene；2-Bromo-5-[5-(5-ethylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 349147-66-6
• 化学式: C₁₄H₁₁BrS₃
• 分子量: 355.343
• InChiKey: ZWWLRVRZOINZFI-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C (decomp)(Solv: hexane (110-54-3))
• 沸点：
  403.2±40.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-ethyl-5''-bromo-2,2':5',2''-terthiophene 、 二氯二甲基锗 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以44%的产率得到
  参考文献：
  名称：

  噻吩并gerger衍生物中的分子内能量转移

  摘要：

  由于其扩展的共轭性，高的化学稳定性和良好的发射特性，双硫代诺耳（DTG）已被用作有机光电器件的光学/半导体材料的有用构建单元。尽管DTG在Ge原子上有两个取代基，但在先前的工作中，这些取代基仅限于简单的烷基和芳基。在这项工作中，为进一步揭示该有用构建单元的新功能，在DTG的Ge上引入了各种π共轭基团。预计引入π共轭基团将在取代基和DTG核之间产生有效的能量转移，这些取代基与Ge原子相邻并连接。如此制备的DTG化合物与芴，对噻吩，Ge上的and和units单元在取代基和DTG核上具有分离良好的前沿轨道，这已通过吸收光谱和DFT计算得到证明。即使能量供体被光激发，取代的DTG衍生物也仅从能量受体显示出清晰的发射。这表明这些化合物中的高效能量转移。我们还准备了更多π扩展的化合物DTGFl2-Ph在DTG噻吩环上带有苯基。DTGFl2-Ph在可见光区域显示出强发射，并具有有效的能量传递特性。这些结

  DOI：

  10.1002/chem.201805418
• 作为产物：
  描述：

  5-ethyl-2,2':5',2''-terthiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以80%的产率得到5-ethyl-5''-bromo-2,2':5',2''-terthiophene
  参考文献：
  名称：

  Preparation of Poly(silylene-p-phenylene)s Containing a Pendant Fluorophor and Their Applications to PL Imaging

  摘要：

  Poly(silylene-p-phenylene)s bearing an anthrylethynyl, pyrenylethynyl, or terthienyl group as the pendant were obtained in moderate yield, by substitution reactions of poly [ethoxy(methyl)silylene-p-phenylene] with the corresponding organolithium reagents in THF. The polymers exhibited photoluminescent (PL) properties in solutions as well as in the films. They were photoactive and irradiation of the films in air with a low-pressure mercury lamp led to a decrease of PL efficiencies, being applicable to PL imaging of the films. The present polymers can be used also as hole-transporting materials in double-layer electroluminescent (EL) devices and the devices with the structure of ITO/polymer film/Alq3/Mg-Ag emitted a green EL arising from Alq3 emission.

  DOI：

  10.1021/ma040108p

文献信息

• Effects of the silicon core structures on the hole mobility of star-shaped oligothiophenes
  作者：Joji Ohshita、Yosuke Hatanaka、Shigenori Matsui、Tomonobu Mizumo、Yoshihito Kunugi、Yoshihito Honsho、Akinori Saeki、Shu Seki、Julius Tibbelin、Henrik Ottosson、Takae Takeuchi

  DOI：10.1039/c0dt00224k

  日期：——

  know more about the effects of the organosilicon core structures on the intermolecular hole mobility, we calculated internal reorganization energies for hole transfer at the (U)B3LYP/6-311+G(d,p)//(U)B3LYP/6-31G(d) level, which suggested smoother intermolecular charge transfer in the silicon derivative than the carbon and germanium analogues. Star-shaped compounds with quarterthiophene units behave

  制备了通过有机硅核连接具有三个或四个低聚噻吩单元的星形化合物，并研究了它们的空穴传输能力。具有气相沉积膜的顶接触型薄膜晶体管（TFT）三[（乙基叔硫苯基）二甲基甲硅烷基]甲基硅烷（3T 3的Si 4）显示的场效应迁移率（μ FET的4.4×10）-5厘米2 V -1s -1，而带有碳心类似物的设备三[（乙基叔硫苯基）二甲基甲硅烷基]甲烷（3T 3 Si 3 C）没有显示TFT活性。通过时间分辨微波电导率测量确定3T 3 Si 4和3T 3 Si 3 C的固有分子内空穴迁移率分别为8×10 -2和2×10 -2 cm 2 V -1s -1分别是由3T 3 Si 4中较高的σ-π相互作用度引起的。要了解有关有机硅核心结构对分子间空穴迁移率的影响的更多信息，我们计算了在（U）B3LYP / 6-311 + G（d，p）//（U）B3LYP / 6处空穴转移的内部重组能-31G（d）能级，表明硅衍
• 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。
• 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).