(E)-bis(2,2'-bithiophene-5-yl)ethylene | 107267-10-7

• 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: (E)-bis(2,2'-bithiophene-5-yl)ethylene
• 英文别名: 1,2-bis[2-(2-thienyl)-5-thienyl]ethene；(E)-1,2-bis-(2,2'-bithiophene-5-yl)ethylene；(E)-1,2-bis[2,2'-bithienyl]vinylene；2-thiophen-2-yl-5-[(E)-2-(5-thiophen-2-ylthiophen-2-yl)ethenyl]thiophene
• CAS: 107267-10-7
• 化学式: C₁₈H₁₂S₄
• 分子量: 356.557
• InChiKey: WHIPBZVMUZAWFT-AATRIKPKSA-N

物化性质

• 熔点：
  190 °C(Solv: ethanol (64-17-5))
• 沸点：
  529.2±50.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2'-联二噻吩 在 四氯化钛 、 锌 、 三氯氧磷 作用下， 反应 5.5h， 生成 (E)-bis(2,2'-bithiophene-5-yl)ethylene
  参考文献：
  名称：

  Preparation of (E)-1,2-Bis(2,2'-bithiophene-5-yl)ethylene and (E)-1,2-Bis-(2,2':5',2''-terthiophene-5-yl)ethylene

  摘要：

  DOI：

  10.3987/r-1986-09-2639

文献信息

• Electronic properties of thienylene vinylene oligomers: synthesis and theoretical study
  作者：G. Neculqueo、V. Rojas Fuentes、A. López、R. Matute、S. O. Vásquez、F. Martínez

  DOI：10.1007/s11224-012-9979-0

  日期：2012.12

  (E)-1,2-bis(2-thienyl)vinylene (TV), (E)-1,2-bis(3-octyl-2-thienyl)vinylene (TOV), (E)-1,2-bis(3-(2-ethylhexyl)-2-thienyl)vinylene (T2EHV), and (E)-1,2-bis-[2,2’-bithienyl] vinylene (BTV) have been synthesized by a combination of formylation reaction and Mc Murry dimerization. UV–Vis spectra of BTV showed the longest wavelength absorption, TOV and T2EHV showed a bathochromic shift to the red compared with TV, due to an increment of delocalization of the conjugated π-system as the result of the weakening of the carbon–carbon double bonds of the thienyl rings due to the substitution of one hydrogen by the alkyl group. Based on optical data, the effect of linear and branched alkyl chain and extension of conjugation length on the electronic properties is discussed. 1H, 13C-NMR, UV–Visible, Fluorescence data are discussed and theoretical DFT and TD-DFT calculations of ground state and excited states have been also considered in the analysis and explanation of results.

  (E)-1,2-双(2-噻吩基)亚乙烯基 (TV)、(E)-1,2-双(3-辛基-2-噻吩基)亚乙烯基 (TOV)、(E)-1,2-通过甲酰化组合合成了双(3-(2-乙基己基)-2-噻吩基)亚乙烯基(T2EHV)和(E)-1,2-双-[2,2'-联噻吩基]亚乙烯基(BTV)反应和 Mc Murry 二聚化。 BTV 的紫外-可见光谱显示出最长的波长吸收，TOV 和 T2EHV 与 TV 相比显示出红移，这是由于碳-碳双键减弱导致共轭 π 系统的离域增加。由于一个氢被烷基取代而形成的噻吩环键。基于光学数据，讨论了直链和支链烷基链以及共轭长度的延长对电子性能的影响。讨论了 1H、13C-NMR、紫外可见光、荧光数据，并在结果分析和解释中考虑了基态和激发态的理论 DFT 和 TD-DFT 计算。
• ORGANIC SEMICONDUCTOR ELEMENT AND METHOD FOR PRODUCING SAME, COMPOUND, ORGANIC SEMICONDUCTOR COMPOSITION AND ORGANIC SEMICONDUCTOR FILM AND METHOD FOR PRODUCING SAME
  申请人：FUJIFILM Corporation

  公开号：EP3258513A1

  公开（公告）日：2017-12-20

  Objects of the present invention are to provide an organic semiconductor element in which carrier mobility is high, variation of mobility is suppressed, and temporal stability under high temperature and high humidity is excellent, and a manufacturing method thereof, to provide a novel compound suitable for an organic semiconductor, and to provide an organic semiconductor film in which mobility is high, variation of mobility is suppressed, and temporal stability under high temperature and high humidity is excellent, a manufacturing method thereof, and an organic semiconductor composition that can suitably form the organic semiconductor film. The organic semiconductor element according to the present invention is an organic semiconductor layer containing a compound having a constitutional repeating unit represented by Formula 1 and having a molecular weight of 2,000 or greater.         (̵D-A)̵     (1)

  本发明的目的是提供一种载流子迁移率高、迁移率变化受抑制、高温高湿条件下的时间稳定性优异的有机半导体元件及其制造方法，提供一种适用于有机半导体的新型化合物，并提供一种迁移率高、迁移率变化受抑制、高温高湿条件下的时间稳定性优异的有机半导体薄膜及其制造方法，以及一种可适当形成该有机半导体薄膜的有机半导体组合物。 根据本发明的有机半导体元件是一种有机半导体层，其中含有一种化合物，该化合物具有由式 1 表示的构型重复单元，且分子量大于等于 2,000。 (̵D-A)̵ (1)
• Effect of Local Molecular Structure on the Chain-Length Dependence of the Electronic Properties of Thiophene-Based π-Conjugated Systems
  作者：Pierre Frère、Jean-Manuel Raimundo、Philippe Blanchard、Jacques Delaunay、Pascal Richomme、Jean-Louis Sauvajol、Jesus Orduna、Javier Garin、Jean Roncali

  DOI：10.1021/jo034319o

  日期：2003.9.1

  Three series of thiophene-based pi-conjugated oligomers built with different combinations of thiophene cycles and double bonds have been synthesized and characterized. The analysis of the chain length dependence of the electronic, electrochemical, and vibrational properties of the three series of oligomers has been carried out using cyclic voltammetry, UV-vis, IR, and Raman spectroscopies. These various investigations provide consistent results showing that incorporation of ethylenic linkages in an oligothiophene structure leads to a faster decrease of the HOMO-LUMO gap with chain extension due to the combined effects of enhanced planarity and lower overall aromatic character of the system. Although the incorporation of two consecutive double bonds in the system leads to a stabilization of the dicationic state, this structural modification does not produce the expected further decrease of the HOMO-LUMO gap at large chain extension. This phenomenon is discussed on the basis of an interplay between aromaticity and bond length alternation.
• Preparation of (E)-1,2-Bis(2,2'-bithiophene-5-yl)ethylene and (E)-1,2-Bis-(2,2':5',2''-terthiophene-5-yl)ethylene
  作者：Juzo Nakayama、Shigeru Murabayashi、Masamatsu Hoshino

  DOI：10.3987/r-1986-09-2639

  日期：——