5-(trimethylsilyl)-2,2'-bithiophene | 161746-01-6

• 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'-bithiophene
• 英文别名: Trimethyl-(5-thiophen-2-ylthiophen-2-yl)silane
• CAS: 161746-01-6
• 化学式: C₁₁H₁₄S₂Si
• 分子量: 238.45
• InChiKey: WCIRSCOSKUAOLP-UHFFFAOYSA-N

物化性质

• 沸点：
  295.5±30.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  5-(trimethylsilyl)-2,2'-bithiophene 在 四(三苯基膦)钯 、 正丁基锂 、 一氯化碘 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 91.0h， 生成 C₃₂H₂₂I₂S₄
  参考文献：
  名称：

  大环寡聚噻吩与立体[2.2]环环骨架：从π-环过相互作用的手性。

  摘要：

  合成了一个新的环状低聚噻吩的对映体，该对映体由两个假邻位[2.2]对环环烷桥接，是一类新的手性π共轭体系。X射线单晶衍射分析表明，这些低聚噻吩由于环烷部分的扭转而产生扭曲的结构。由于较大的磁/电跃迁偶极矩，将低聚噻吩嵌入固有的平面手性中可显着增强圆二色性（CD）光谱。在药物状态下，由于寡噻吩的强相互作用而形成了分子内的π二聚体。我们进一步记录了250-1800 nm区域CD光谱的空前广泛的范围。通过寡噻吩的激子偶联合理地描述了转变。

  DOI：

  10.1002/chem.201605842
• 作为产物：
  描述：

  2,2'-联二噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 生成 5-(trimethylsilyl)-2,2'-bithiophene
  参考文献：
  名称：

  Characterization of the conductivity of organic thiols by field emission microscopy and field emission spectroscopy

  摘要：

  The conducting properties of two organic thiols (5-mercapto-2,2'-bithiophene and 4-mercaptobiphenyl) deposited by the self-assembly method on Pt tips have been characterized in ultrahigh vacuum by field emission microscopy and spectroscopy. It was shown that these two molecular species can be successfully adsorbed from solution on the Pt tip. The presence of the molecules causes a large decrease in the required field emission voltages by a factor of similar to 3-5. Measurement of the total energy distributions of the emitted electrons showed that the electrons are emitted from a narrow band which is not pinned at the Fermi level but which shifts to lower energy with increased applied field. The molecules thus appear more like an insulator than a conductor. Significant current-induced heating of the molecules was found: for example, Delta T approximate to 80 K for 0.3 nA. Taken together these properties pose problems for the use of these and similar one-dimensional molecules as current-carrying connections in proposed nanoscale electronic applications. However, when used in the subpicoampere range, the current through the wire may be sustainable and dissipation small. In general, these experiments open a door to exploring other molecules.

  DOI：

  10.1021/ja00105a045

文献信息

• Branched oligothiophene silanes with the efficient nonradiative energy transfer between the fragments
  作者：O. V. Borshchev、S. A. Ponomarenko、E. A. Kleymyuk、Yu. N. Luponosov、N. M. Surin、A. M. Muzafarov

  DOI：10.1007/s11172-010-0164-6

  日期：2010.4

  The synthesis of new dendrimers and branched oligothiophene silanes containing bithiophene groups at the periphery and quaterthiophene fragments at the center of the molecule is described. Specific features of bithiophene silane bromination were shown, and the conditions for the efficient synthesis of methyltris(5-bromo-2,2′-bithiophen-5-yl)silane have been found for the first time. The optical properties

  描述了新的树枝状聚合物和支链低聚噻吩硅烷的合成，这些硅烷的外围含有联噻吩基团，分子中心含有四联噻吩片段。展示了联噻吩硅烷溴化的具体特征，并首次发现了有效合成甲基三（5-溴-2,2'-联噻吩-5-基）硅烷的条件。研究了合成化合物的光学性质。测量了支化双和季噻吩硅烷片段之间的电子激发能量转移效率。
• 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。
• Influence of the structure of electron-donating aromatic units in organosilicon luminophores based on 2,1,3-benzothiadiazole electron-withdrawing core on their absorption-luminescent properties
  作者：Maxim S. Skorotetcky、Evgeniya D. Krivtsova、Oleg V. Borshchev、Nikolay M. Surin、Evgeniya A. Svidchenko、Yuriy V. Fedorov、Sergey A. Pisarev、Sergey A. Ponomarenko

  DOI：10.1016/j.dyepig.2018.03.043

  日期：2018.8

  characterized. Investigation of their absorption-luminescent properties revealed that all of them possess high photoluminescence (PL) quantum yield and large Stokes shift both in diluted solutions and polymer matrix, while in the solid state their PL efficiency decreases. It was found that the main factor influencing the optical properties of the molecules obtained is the type of aromatic fragment directly

  一系列新的线性π共轭低聚物，由五个基于2,1,3-苯并噻二唑（BTD）吸电子基团的共轭环以及2,5-噻吩和1,4-亚苯基给电子单元的各种组合组成已经合成并表征了末端三甲基甲硅烷基。对它们的吸收发光性质的研究表明，它们在稀释溶液和聚合物基质中均具有高的光致发光（PL）量子产率和大的斯托克斯位移，而在固态时它们的PL效率下降。发现影响获得的分子的光学性质的主要因素是直接附接到中央BTD部分的芳族片段的类型。将供体芳香族片段的化学结构从1,1'-联苯改变为2，2'-联噻吩可在510至660 nm的宽范围内调节发光体的PL光谱最大值。结果表明，在这些发光体中三甲基甲硅烷基的存在是它们增加的溶解度，增加的摩尔消光系数和缩短激发态寿命而不降低PL效率的原因。
• Photoswitching of Solvatochromism Using Diarylethenes with 2,5-Disubstituted 3-Thienyl Unit
  作者：Naoki Tanifuji、Masahiro Irie、Kenji Matsuda

  DOI：10.1246/cl.2007.1232

  日期：2007.10.5

  Novel photochromic bis(3-thienyl)ethene with a 2,5-disubstituted thienyl unit, which shows photoswitching of solvatochromic property, was synthesized. The open-ring isomer showed solvatochromic behavior, while the closed-ring isomer did not. It was suggested that the alteration of the π-conjugated bond structure is the main cause of the switching of the solvatochromic property.

  合成了具有2,5-二取代噻吩基单元的新型光致变色双(3-噻吩基)乙烯，其具有溶剂化变色特性的光开关。开环异构体表现出溶剂化变色行为，而闭环异构体则没有。有人认为，π-共轭键结构的改变是溶剂化变色性质转变的主要原因。
• Palladium-Catalyzed Direct (Het)arylation Reactions of Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole and 4,8-Dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)
  作者：Timofey N. Chmovzh、Timofey A. Kudryashev、Daria A. Alekhina、Oleg A. Rakitin

  DOI：10.3390/molecules28093977

  日期：——

  bromo(iodo)arenes and -thiophenes in the presence of Pd(OAc)2 and di-tert-butyl(methyl)phosphonium tetrafluoroborate salt is a powerful tool for the selective formation of 4-mono- and 4,8-di(het)arylated benzo-bis-thiadiazoles. Oxidative double C–H hetarylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with thiophenes in the presence of Pd(OAc)2 and silver (I) oxide in DMSO was successfully employed to prepare

  钯催化的强吸电子三环苯并[1,2-d:4,5-d']双（[1,2,3]噻二唑）及其4,8-二溴衍生物的直接（杂）芳基化反应研究过；发现了选择性形成单芳基和双芳基衍生物的条件。4,8-二溴苯并[1,2-d:4,5-d']双([1,2,3]噻二唑)与噻吩在乙酸钯为催化剂、新戊酸钾为碱的条件下的反应, 根据所使用的条件, 选择性地以低到中等的收率得到单-和双-噻吩基化的苯并-双-噻二唑; 发现芳烃在这些反应中没有活性。发现苯并 [1,2-d:4,5-d']bis([1,2, 3]噻二唑与溴（碘）芳烃和-噻吩在 Pd(OAc)2 和二叔丁基（甲基）四氟硼酸盐存在下是选择性形成 4-单-和 4,8 的有力工具-二（杂）芳基化苯并双噻二唑。在 Pd(OAc)2 和氧化银 (I) 存在下苯并 [1,2-d:4,5-d'] 双 ([1,2,3] 噻二唑与噻吩的氧化双 C-H 杂芳化反应DMSO 成功地用于以中等收率制备双噻吩基苯并双噻二唑。