bis(3-bromobenzo[b]thiophen-2-yl)dimethylsilane | 1193393-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: bis(3-bromobenzo[b]thiophen-2-yl)dimethylsilane
• 英文别名: bis(3-bromobenzo[b]thiophene)dimethylsilicon；Bis(3-bromo-1-benzothiophen-2-yl)-dimethylsilane
• CAS: 1193393-13-3
• 化学式: C₁₈H₁₄Br₂S₂Si
• 分子量: 482.335
• InChiKey: BCRKDOACYHLPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  bis(3-bromobenzo[b]thiophen-2-yl)dimethylsilane 、 二甲基二氯化锡 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 16.92h， 以80%的产率得到1,1,4,4-tetramethylbis(benzo[b]thieno)[2,3-b:3′,2′-e][1,4-dihydro-1,4]silastannin
  参考文献：
  名称：

  Benzo[b]thiophene-Fused Boron and Silicon Ladder Acenes

  摘要：

  Synthetic routes to three new heteroacene compounds in which two benzo[b]thienyl units are bridged by dimethylsilyl and/or mesitylboryl units are described. In the Si/Si and Si/B compounds 1-syn and 3-syn, respectively, the sulfur atoms of the flanking benzo[b]thiophenes are disposed in meta positions on the central six-membered heterocycle, while in the B/B compound 4-anti, they are para to each other; the reasons for this lie in the synthetic method employed to prepare 4-anti. All three compounds were crystallographically characterized and their photophysical properties examined. A comprehensive examination of their photophysical properties shows that they are weakly absorbing and fluorescing materials, with the diborin derivative 4-anti exhibiting the most red-shifted absorption maxima and largest fluorescence quantum yield.

  DOI：

  10.1021/om4004187
• 作为产物：
  描述：

  2,3-二溴苯并[b]噻吩 、 二氯二甲基硅烷 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.67h， 以60%的产率得到bis(3-bromobenzo[b]thiophen-2-yl)dimethylsilane
  参考文献：
  名称：

  Synthesis and properties of ladder-type 1,4-dihydro-1,4-phosphasilins

  摘要：

  报告了一系列扩展二噻吩并[2,3-b:3′,2′-e][1,4-二氢-1,4]磷脂酰亚胺的合成和高级表征，并评估了它们作为有机电子学新构件的适用性。使用适当的 2,3-二溴噻吩前体，通过随后引入硅和磷中心的两步法，可以合成基本的和苯延伸的二噻吩亚磷酸。这两种阶梯型材料都显示出三价磷物种的典型反应性，并可定量转化为相应的氧化物或金络合物，后者以碱性二噻吩磷络合物为例。研究发现，它们的光电特性不如相关的二噻吩并[3,2-b:2′,3′-d]磷烯，这表明分子支架中的π-共轭发生了破坏。X 射线晶体学研究表明，氧化苯延伸材料的分子支架是平面的，而碱性二噻吩材料的分子支架与平面性有一些微小的偏差。密度泛函理论计算表明，除了苯延伸的三价磷脂酰亚胺外，所有材料都是平面的。这项结构-性质研究表明，扩展的磷脂酰亚胺分子支架中的π-共轭关系的破坏完全是由于硅中心的存在及其电子效应，而不是结构特征。

  DOI：

  10.1139/v09-108

文献信息

• Ladder-Type π-Conjugated 4-Hetero-1,4-dihydrophosphinines: A Structure-Property Study
  作者：Yi Ren、Thomas Baumgartner

  DOI：10.1002/asia.201000196

  日期：——

  Abstractπ‐Conjugated six‐membered 1,4‐dihydrophosphinines containing a heteroatom (Si, P, S) at the 4 position were synthesized and systematically studied. X‐ray crystallographic analyses showed that the central six‐membered heterocyclic rings are almost planar. The sum of the angles around the phosphorus atom increases by 23° from the trivalent phosphorus to the phosphonium atom in the thiaphosphinine system, which is consistent with the NMR spectroscopic studies. UV/Vis spectroscopy and theoretical calculations revealed that the communication between the phosphorus center and the benzothiophene moiety is enhanced by the incorporation of a sulfur atom into the molecular scaffold. The increased conjugation endows the thiaphosphinines with interesting emission properties. Theoretical calculations supported the postulation that the orbital coupling between the π system and a σ* orbital could be enhanced in the thiaphosphinine system, especially through a phosphonium center. Cyclic voltammetry studies revealed that the thiaphosphinine oxide, thiaphosphonium, and cis‐diphosphinine oxide exhibit quasi‐reversible reduction processes, which demonstrate that simple changes in the bridge heteroatoms help to efficiently tune the redox properties of the ladder‐type 4‐hetero‐1,4‐dihydrophosphinines.