2-dicyanovinyl-5-(4-ethoxyphenyl)thiophene | 1228958-80-2

• 英文名称: 2-dicyanovinyl-5-(4-ethoxyphenyl)thiophene
• 英文别名: 2-[[5-(4-Ethoxyphenyl)thiophen-2-yl]methylidene]propanedinitrile
• CAS: 1228958-80-2
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: IZQYWWDNXLJBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-formyl-5-(4'-ethoxyphenyl)thiophene 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-dicyanovinyl-5-(4-ethoxyphenyl)thiophene
  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.