5-trimethylsilyl-2,2':5',2''-terthienyl | 118824-87-6

• 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-trimethylsilyl-2,2':5',2''-terthienyl
• 英文别名: 5-(trimethylsilyl)-2,2':5',2''-terthiophene；5-dimethysilyl-2,2',5',2''-terthiophene；Silane, trimethyl[2,2':5',2''-terthiophen]-5-yl-；trimethyl-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]silane
• CAS: 118824-87-6
• 化学式: C₁₅H₁₆S₃Si
• 分子量: 320.576
• InChiKey: JAQWBFQUZZSZDU-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  393.9±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-trimethylsilyl-2,2':5',2''-terthienyl 在 四(三苯基膦)钯 、 正丁基锂 、 三乙基硼氢化锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 40.17h， 生成
  参考文献：
  名称：

  分子二元与多组分方法——低聚噻吩光敏剂与[FeFe]-氢化酶模拟物相结合的光催化析氢

  摘要：

  合成了一种[FeFe]-氢化酶启发的光催化剂（PS-CAT），用于在可见光照射下析氢。为了阐明光活性和催化部分之间的共价键对催化活性的影响，通过纳秒瞬态吸收和光催化 H 2

  DOI：

  10.1002/cctc.202400247
• 作为产物：
  描述：

  2,2'-联二噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 氯仿 、 甲苯 为溶剂， 生成 5-trimethylsilyl-2,2':5',2''-terthienyl
  参考文献：
  名称：

  针对分子融合电子设备应用的正交融合共轭低聚物的融合合成途径。

  摘要：

  本文介绍了针对分子规模电子设备构建项目的合成有机相。概述了向正交融合的共轭有机低聚物的聚合合成路线。最终系统应具有一条通过sigma键合网络与第二条潜在导电链垂直融合的潜在导电链。合成的核心链段之一是基于具有中心硅原子的螺二噻吩部分。它由四炔丙基硅烷的锆促进的双（双环化）形成。第二个核心是9,9'-螺双芴系统。末端卤化物基团通过Pd催化或Pd / Cu催化的交叉偶联方法提供了用于链的进一步延伸的连接点。所有四个分支臂都可以在一次操作中固定到核心，因此使合成高度收敛。在较大的官能化系统的情况下，噻吩上的烷基取代基提供可溶的物质。为了制备长度> 50Å的分子，必须使用迭代的发散/收敛方法来构建低聚（噻吩-乙炔）支链。有机钯催化的方法被广泛用于正交稠合化合物的合成。

  DOI：

  10.1021/jo960897b

文献信息

• Synthesis, structure and cytotoxicity of trimethylsilyl oligothienylcarbaldehydes and their derivatives
  作者：Edmunds Lukevics、Giovanna Barbarella、Pavel Arsenyan、Irina Shestakova、Sergey Belyakov、Juris Popelis、Olga Pudova

  DOI：10.1016/s0022-328x(01)00835-x

  日期：2001.11

  Trimethylsilyl end-capped bi- and terthiophene carbaldehydes were prepared by reaction of bi- and terthienyl lithium with DMF. Condensation of 5-trimethylsilyl-2,2′-bithiophene-5′-carbaldehyde with dinitrile of malonic acid gave silylbithienyl methylidenedinitrile in good yield, while reaction with hydroxylamine was accompanied by desilylation. The reaction of hydroxylamine with silylbithienyldinitrile

  通过联和叔噻吩基锂与DMF的反应制备三甲基甲硅烷基封端的联噻吩和对噻吩甲醛。5-三甲基甲硅烷基-2,2'-联噻吩-5'-甲醛与丙二酸二腈缩合可得到高收率的甲硅烷基苯噻吩基甲基化二烯腈，而与羟胺的反应则伴随着甲硅烷基化反应。羟胺与甲硅烷基二苯甲基二腈的反应导致形成2- [5-（5'-三甲基甲硅烷基-2,2'-二苯甲基）亚甲基]丙二酸双酰胺肟。在体外研究了联噻吩和对噻吩衍生物对两种单层肿瘤细胞系MG-22A（小鼠肝癌）和HT-1080（人纤维肉瘤）的细胞毒性作用。通过X射线衍射研究了5-三甲基甲硅烷基-2,2'-联噻吩-5'-甲醛的分子结构。
• Synthesis and characterization of alkyl-, halo- and hetero-substituted derivatives of the potent phototoxin α-terthienyl
  作者：Anita Mac Eachern、Chantal Soucy、Leonard C. Leitch、John T. Arnason、Peter Morand

  DOI：10.1016/s0040-4020(01)81692-6

  日期：1988.1
• Structure of Thiophene-Based Regioregular Polymers and Block Copolymers and Its Influence on Luminescence Spectra
  作者：Paul F. van Hutten、Richard E. Gill、Jan K. Herrema、Georges Hadziioannou

  DOI：10.1021/j100010a036

  日期：1995.3

  Two approaches toward control of the luminescence wavelength of polythiophenes have been explored: (i) block copolymers in which oligothiophene blocks alternate with oligosilanylene blocks and (ii) regioregular polythiophenes in which oligothiophene sequences are delimited by n-octyl substituents placed in a ''head-to-head'' fashion on adjacent rings. Both methods aim at restricting the pi-conjugation to the oligothiophene sequences. The block copolymer approach is very effective, whereas the (solution) luminescence spectra of the regioregular polymers are strongly red-shifted with respect to absorption and confined to a narrow range of wavelengths. This is due to the quinoid character of the excited singlet state, in which there is a strong electronic driving force toward coplanarity of adjacent thiophene rings, which offsets the steric hindrance of the octyl substituents and increases the size of the conjugating pi-system. This explanation is supported by calculations and by spectral data of substituted bithiophenes.
• Synthesis and optical properties of compounds via platinum-catalyzed hydrosilylation of triethynyltriazine and silyl-substituted oligothiophenes
  作者：Akinobu Naka、Sakino Takase、Haruka Komuro、Kaori Uemura、Mizuki Yoshioka、Hisayoshi Kobayashi、Joji Ohshita、Yohei Adachi、Mitsuo Ishikawa

  DOI：10.1016/j.jorganchem.2020.121275

  日期：2020.6

  New types of starlike compounds and branched polymers with a triazine core and silylbithienyl or silylterthienyl arms were prepared by the use of platinum-catalyzed hydrosilylation. The UV-Vis absorption and fluorescence properties of these molecules have been investigated. In the fluorescence spectra of the silylbithienyl substituted starlike compound, their emission maxima derived from the bithiophene units were observed. In the branched polymer with silylbithienyl units, a peak derived from the interaction between the triazine and bithienyl units was observed at about 500 nm. No significant difference between the starlike compound and branched polymer with silylterthienyl units was observed in their UV-Vis absorption and fluorescence spectra. DFT calculations were performed to understand the photophysical properties of the starlike molecules with silylbithienyl and silylterthienyl arms. (C) 2020 Elsevier B.V. All rights reserved.
• EACHERN, ANITA MAC;SOUCY, CHANTAL;LEITCH, LEONARD C.;ARNASON, JOHN T.;MOR+, TETRAHEDRON, 44,(1988) N 9, 2403-2412
  作者：EACHERN, ANITA MAC、SOUCY, CHANTAL、LEITCH, LEONARD C.、ARNASON, JOHN T.、MOR+

  DOI：——

  日期：——