(Z)-1,2-bis(3-bromothiophen-2-yl)ethene | 40033-68-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: (Z)-1,2-bis(3-bromothiophen-2-yl)ethene
• 英文别名: cis-1,2-Di-(3-brom-2-thienyl)-aethen；3,3'-dibromo-2,2'-cis-ethene-1,2-diyl-bis-thiophene；3-bromo-2-[(Z)-2-(3-bromothiophen-2-yl)ethenyl]thiophene
• CAS: 40033-68-9
• 化学式: C₁₀H₆Br₂S₂
• 分子量: 350.098
• InChiKey: VDOQKHMSNJVSJS-UPHRSURJSA-N

物化性质

• 沸点：
  394.7±37.0 °C(Predicted)
• 密度：
  1.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (Z)-1,2-bis(3-bromothiophen-2-yl)ethene 以70%的产率得到
  参考文献：
  名称：

  GRONOWITZ S .; DAHLGREN T., CHEM. SER., 1977, 12, NO 2-3, 57-67

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(3-bromo-2-thienyl)acetylene 在 二异丁基氢化铝 作用下， 以 正己烷 为溶剂， 以60 %的产率得到(Z)-1,2-bis(3-bromothiophen-2-yl)ethene
  参考文献：
  名称：

  10.1002/anie.202410204

  摘要：

  Positively charged phosphorus‐containing heterocycles are characteristic core skeletons for functional molecules. While various phosphonium‐containing five‐ or six‐membered ring compounds have been reported, seven‐membered ring phosphepinium has not yet been fully studied. In this study, dithieno[2,3‐b;3,2‐f]phosphepinium ions containing electron‐donating aminophenyl groups were synthesized. An X‐ray crystallographic analysis of the resulting donor‐acceptor‐donor dyes revealed a bent conformation of the central seven‐membered ring. This compound exhibited fluorescence in the near‐infrared region with a bathochromic shift of 70 nm compared to phosphepine oxide congener and a large Stokes shift. High fluorescence quantum yields were obtained even in polar solvents due to the suppression of the nonradiative decay process. The theoretical study revealed that the phosphepinium skeleton is highly electron‐accepting owing to the orbital interaction between a px orbital of the phosphonium moiety and a π* orbital of the 1,3,5‐hexatriene moiety. Owing to the lower‐lying px orbital in the phosphonium moiety compared with that of the phosphine oxide and the bent conformation of the seven‐membered ring, the phosphepinium ring effectively furnishes a px‐π* conjugation. A large structural relaxation with the contribution of a quinoidal resonance structure is suggested in the excited state, which is responsible for the intense emission with a large Stokes shift.

  DOI：

  10.1002/anie.202410204

文献信息

• Thiophene-Fused Borepins As Directly Functionalizable Boron-Containing π-Electron Systems
  作者：David R. Levine、Maxime A. Siegler、John D. Tovar

  DOI：10.1021/ja502644e

  日期：2014.5.14

  preparation of two isomeric dithienoborepins (DTBs), boron-containing polycyclic aromatics featuring the fusion of borepin and thiophene rings. DTBs exhibit reversible cathodic electrochemistry and boron-centered Lewis acidity in addition to enhanced electronic delocalization relative to benzo-fused analogues. Boron's precise position within the conjugation pathway of DTBs significantly affected electronic

  开发了用于克级制备两种异构体二噻吩硼烷 (DTB) 的合成方案，这是一种以硼烷和噻吩环融合为特征的含硼多环芳烃。除了相对于苯并稠合类似物增强的电子离域外，DTB 还表现出可逆的阴极电化学和以硼为中心的路易斯酸度。硼在 DTBs 共轭通路中的精确位置显着影响了电子结构，最清楚地证明了每个异构体对氟离子结合的光谱响应的变化。除了在空气和水分存在下具有出色的稳定性外，DTBs 还可以进行亲电芳香取代和金属化化学，后者能够实现未取代的噻吩环的直接、区域特异性功能化。随后通过安装供体和受体 π 取代基实现了分子性质的后续调整，从而产生了具有多步电化学还原和可极化电子结构的化合物。作为可直接官能化、π-共轭、含硼多环芳烃的罕见例子，DTBs 是下一代有机硼 π-电子材料的有前途的基石，除了化学稳定性外，其发展还需要广泛的分子多样化范围。
• Isomeric Dithienophosphepines: The Impact of Ring Fusion on Electronic and Structural Properties
  作者：Kevin Padberg、Johannes D. R. Ascherl、Frank Hampel、Milan Kivala

  DOI：10.1002/chem.201905429

  日期：2020.3.18

  The synthesis and extensive experimental (X-ray crystallography, UV/Vis spectroscopy, cyclic voltammetry) and theoretical (DFT calculations) characterization of two isomeric dithieno[b,f]phosphepines (DTPs) are presented herein. The relative orientation of the phosphepine and the thiophene moieties has a decisive impact on the electronic and structural properties of these compounds. Moreover, the thiophene

  本文介绍了两种异构的二噻吩并[b，f]磷脂（DTP）的合成和广泛的实验（X射线晶体学，UV / Vis光谱，循环伏安法）和理论（DFT计算）表征。磷脂和噻吩部分的相对取向对这些化合物的电子和结构性质具有决定性的影响。此外，噻吩单元可通过直接的Pd催化的CH偶联实现便捷的后续功能化，这使得DTP成为有机磷功能材料的高度有前途的基石。
• Unexpected rearrangement during the gas-phase dehalogenation approach to benzodithiophenes
  作者：R. Alan Aitken、Adebayo O. Oyewale

  DOI：10.1039/c4ra15004j

  日期：——

  As well as the expected dehalogenative coupling products, isomers are formed via a novel radical process.

  除了预期的去卤代偶联产物外，还通过一种新颖的自由基过程形成了异构体。
• EVAPORABLE ORGANIC SEMICONDUCTIVE MATERIAL AND USE THEREOF IN AN OPTOELECTRONIC COMPONENT
  申请人：Hildebrandt Dirk

  公开号：US20130167930A1

  公开（公告）日：2013-07-04

  The invention relates to compounds of general formula IIIa and their use in optoelectronic components.

  本发明涉及通式IIIa化合物及其在光电组件中的使用。
• US9127020B2
  申请人：——

  公开号：US9127020B2

  公开（公告）日：2015-09-08