2-dicyanovinyl-5-phenylthiophene | 771564-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-dicyanovinyl-5-phenylthiophene
• 英文别名: 2-[(5-Phenylthiophen-2-yl)methylidene]propanedinitrile
• CAS: 771564-33-1
• 化学式: C₁₄H₈N₂S
• 分子量: 236.297
• InChiKey: KUTKHGZXVZASIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 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：
  75.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-苯基-2-噻吩甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-dicyanovinyl-5-phenylthiophene
  参考文献：
  名称：

  Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships

  摘要：

  本文介绍了一系列推拉芳基（双）噻吩发色团的光物理和 TPA 特性，这些发色团带有电子捐赠（D）和电子撤回（A）端基，其强度不断增加。所有化合物在可见光区域都显示出强烈的分子内电荷转移（ICT）吸收带。增加 D 和/或 A 的强度以及共轭路径的长度会引起吸收带的浴色和高色移，这与类似推挽多烯的情况相同。然而，与相应的推拉式多烯相比，荧光显著增加。特别是，由苯基-双噻吩共轭路径和带有强 D 和 A 端基的发色团被发现结合了非常大的单光子和双光子亮度，以及在红色/近红外区域的强发射。这些分子有望成为用于生物成像的双光子荧光探针。

  DOI：

  10.1039/c2pp25258a

文献信息

• Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials
  作者：Cyril Herbivo、Alain Comel、G. Kirsch、A. Maurício C. Fonseca、M. Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.dyepig.2010.01.006

  日期：2010.8

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.
• NEW ABSORBER FOR ORGANIC HETEROJUNCTION SOLAR CELLS
  申请人：BASF SE

  公开号：EP3036782B1

  公开（公告）日：2019-10-09
• [EN] NEW ABSORBER FOR ORGANIC HETEROJUNCTION SOLAR CELLS<br/>[FR] NOUVEL ABSORBEUR POUR CELLULES SOLAIRES ORGANIQUES À HÉTÉROJONCTION
  申请人：BASF SE

  公开号：WO2015024851A1

  公开（公告）日：2015-02-26

  The present invention relates to a photoactive material comprising a donor substance and an acceptor substance, wherein the donor substance comprises or consists of one or more compounds of formula (I) described below, or the acceptor substance comprises or consists of one or more compounds of formula (I) described below, or the donor substance comprises or consists of a first compound of formula (I) described below and the acceptor substance comprises a second compound of formula (I) described below with the proviso that the first and second compound are not the same, as well as to an organic solar cell or photodetector comprising said photoactive material. The present invention also relates to a photoelectric conversion device comprising or consisting of two or more organic solar cells comprising said photoactive material and to compounds of formula (I) as described below for use as donor substance or as acceptor substance in a photoactive material.
• Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships
  作者：Emilie Genin、Vincent Hugues、Guillaume Clermont、Cyril Herbivo、M. Cidália R. Castro、Alain Comel、M. Manuela M. Raposo、Mireille Blanchard-Desce

  DOI：10.1039/c2pp25258a

  日期：2012.11

  Photophysical and TPA properties of series of push—pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochromic and hyperchromic shifts of the absorption band as reported for analogous push—pull polyenes. Yet, in contrast with corresponding push—pull polyenes, a significant increase in fluorescence is observed. In particular, chromophores built from a phenyl—bithienyl conjugated path and bearing strong D and A end-groups were found to combine very large one and two-photon brightness as well as strong emission in the red/NIR region. These molecules hold promise as biphotonic fluorescent probes for bioimaging.

  本文介绍了一系列推拉芳基（双）噻吩发色团的光物理和 TPA 特性，这些发色团带有电子捐赠（D）和电子撤回（A）端基，其强度不断增加。所有化合物在可见光区域都显示出强烈的分子内电荷转移（ICT）吸收带。增加 D 和/或 A 的强度以及共轭路径的长度会引起吸收带的浴色和高色移，这与类似推挽多烯的情况相同。然而，与相应的推拉式多烯相比，荧光显著增加。特别是，由苯基-双噻吩共轭路径和带有强 D 和 A 端基的发色团被发现结合了非常大的单光子和双光子亮度，以及在红色/近红外区域的强发射。这些分子有望成为用于生物成像的双光子荧光探针。