2-dicyanovinyl-5-(4-N,N-dimethylaminophenyl)thiophene | 130867-28-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-dicyanovinyl-5-(4-N,N-dimethylaminophenyl)thiophene
• 英文别名: ({5-[4-(dimethylamino)phenyl]thiophen-2-yl}methylidene)propanedinitrile；2-[[5-[4-(Dimethylamino)phenyl]thiophen-2-yl]methylidene]propanedinitrile
• CAS: 130867-28-6
• 化学式: C₁₆H₁₃N₃S
• 分子量: 279.365
• InChiKey: NGLSUGDFPFDEAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-碘-N,N-二甲基苯胺 在 aluminum oxide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 2-dicyanovinyl-5-(4-N,N-dimethylaminophenyl)thiophene
  参考文献：
  名称：

  噻吩插入的芳基-双氰基乙烯基化合物：具有显着红移发射和大斯托克斯位移的第二代荧光分子转子

  摘要：

  荧光分子转子可用作微环境粘度的分子传感器。然而，这些分子转子仅限于 9-(二氰基乙烯基)julolided (DCVJ) 和一些衍生物。此外，这些传统转子表现出短的吸收/发射波长和小的斯托克斯位移。为了解决这些缺点，我们开发了一个小型的用于粘度传感的新型分子转子库，通过将噻吩单元结合到传统的荧光分子转子中来制备，目的是获得具有红移激发/发射波长和更大斯托克斯位移的分子转子。已知的转子。新转子显示出显着改善的光物理特性。例如，转子 4 的吸收/发射波长分别为 559/697 nm，与传统荧光分子转子 DCVJ 的吸收/发射波长 (465/503 nm) 和非常小的斯托克斯位移 (38 nm) 相比，138 nm 的非常大的斯托克斯位移。通过 DFT 计算使转子的光物理特性合理化。

  DOI：

  10.1002/ejoc.201100891

文献信息

• 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。
• 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.
• Synthesis of new thiophene compounds with large second order optical non-linearitles
  作者：G. Mignani、F. Leising、R. Meyrueix、H. Samson

  DOI：10.1016/s0040-4039(00)97721-9

  日期：1990.1
• MIGNANI, G.;LEISING, F.;MEYRUEIX, R.;SAMSON, H., TETRAHEDRON LETT., 31,(1990) N3, C. 4743-4746
  作者：MIGNANI, G.、LEISING, F.、MEYRUEIX, R.、SAMSON, H.

  DOI：——

  日期：——
• Thiophene-Inserted Aryl-Dicyanovinyl Compounds: The Second Generation of Fluorescent Molecular Rotors with Significantly Redshifted Emission and Large Stokes Shift
  作者：Jingyin Shao、Shaomin Ji、Xiaolian Li、Jianzhang Zhao、Fuke Zhou、Huimin Guo

  DOI：10.1002/ejoc.201100891

  日期：2011.10

  into the conventional fluorescent molecular rotors with the aim of accessing molecular rotors with redshifted excitation/emission wavelengths and larger Stokes shifts compared with the known rotors. The new rotors show substantially improved photophysical properties. For example, rotor 4 shows absorption/emission wavelengths of 559/697 nm, respectively, and a very large Stokes shift of 138 nm compared

  荧光分子转子可用作微环境粘度的分子传感器。然而，这些分子转子仅限于 9-(二氰基乙烯基)julolided (DCVJ) 和一些衍生物。此外，这些传统转子表现出短的吸收/发射波长和小的斯托克斯位移。为了解决这些缺点，我们开发了一个小型的用于粘度传感的新型分子转子库，通过将噻吩单元结合到传统的荧光分子转子中来制备，目的是获得具有红移激发/发射波长和更大斯托克斯位移的分子转子。已知的转子。新转子显示出显着改善的光物理特性。例如，转子 4 的吸收/发射波长分别为 559/697 nm，与传统荧光分子转子 DCVJ 的吸收/发射波长 (465/503 nm) 和非常小的斯托克斯位移 (38 nm) 相比，138 nm 的非常大的斯托克斯位移。通过 DFT 计算使转子的光物理特性合理化。