1-(p-cyanophenyl)-4-[p-(dimethylamino)phenyl]-1,3-butadiyne

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(p-cyanophenyl)-4-[p-(dimethylamino)phenyl]-1,3-butadiyne
• 英文别名: 1-(4-cyanophenyl)-4-(4-dimethylaminophenyl)-1,3-butadiyne；1-(4-dimethylaminophenyl)-4-(4-cyanophenyl)-1,3-butadiyne；4-[4-[4-(Dimethylamino)phenyl]buta-1,3-diynyl]benzonitrile
• 化学式: C₁₉H₁₄N₂
• 分子量: 270.334
• InChiKey: SJQNRSSDGVUVNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(p-cyanophenyl)-4-[p-(dimethylamino)phenyl]-1,3-butadiyne 、 蒽酮 在 potassium hydride 、 2-甲基-4-苯基-2-丁醇 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 21.0h， 生成 、
  参考文献：
  名称：

  1,4-二芳基-1-氧基-1,3-丁二烯共轭系统结合在二苯并碲烯骨架中：合成、光物理特性以及与较重的 16 族同系物的比较

  摘要：

  我们已经合成了 1,4-二芳基-1-硫代-、硒-和碲-1,3-丁二烯衍生物并入二苯并碲烯骨架，发现硫代和硒代衍生物在室温下在溶液中具有很强的荧光。我们在这里报告了氧同源物的合成。这些化合物是通过邻氨基苯甲酸与 1,4-二芳基-1,3-丁二炔反应，然后进行分子内环加成反应合成的。通过 X 射线晶体学分析它们的结构，以揭示与较重的硫属元素同类物相比，1,4-二芳基-1-氧基-1,3-丁二烯部分的高度平面性。含氧化合物与硫代和硒同系物类似地发出荧光；二苯基和双（4-三氟苯基）衍生物显示出一些具有振动结构的红移荧光光谱。D-π-A 型衍生物的荧光达到红色和近红外区域。在 DFT 计算的基础上讨论了 1-chalcogeno-1,3-butadiene 部分的键合特征。

  DOI：

  10.1246/bcsj.20160287
• 作为产物：
  描述：

  4-乙炔基苯甲腈 、 4-二甲基氨基苯乙炔 在 氧气 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 以52 %的产率得到1-(p-cyanophenyl)-4-[p-(dimethylamino)phenyl]-1,3-butadiyne
  参考文献：
  名称：

  Greener photocatalytic route to the hetero-selective Glaser coupling reaction: role of hole/oxygen in air

  摘要：

  设计的纳米光催化剂[CuII@TiO2]可在绿色溶剂中高效地进行异选择性格拉塞偶联反应，并具有优异的翻转次数。空气中的光和空穴/O2 可维持催化循环，实现反应的空间/时间控制。

  DOI：

  10.1039/d2cy01439d

文献信息

• Novel diacetylenic and polydiacetylenic compositions
  申请人：CELANESE CORPORATION

  公开号：EP0243807A2

  公开（公告）日：1987-11-04

  This invention provides a novel case of diacetylenic monomers and corresponding polydiacetylenic polymers. Illustrative of the invention is a polymer characterized by the repeating unit: In the form of an optically transparent medium with a noncentrosymmetric alignment of molecules, the polymer exhibits exceptional second order nonlinear optical susceptibility effects.

  本发明提供了一种新型二乙炔单体和相应的聚二乙炔聚合物。 本发明的聚合物具有以下重复单元：在分子非中心对称排列的光学透明介质形式中，该聚合物表现出特殊的二阶非线性光学感性效应。
• Red and Near-Infrared Photoluminescence of D-π-A-Type Compounds Based on a 1,4-Diaryl-1-thio-1,3-butadiene Conjugated System in a Dibenzobarrelene Skeleton
  作者：Akihiko Ishii、Yukihiro Makishima、Norio Nakata

  DOI：10.1021/acs.joc.5b02189

  日期：2015.11.20

  1,4-Diaryl-1-thio-1,3-butadiene derivatives having a pi-donor dimethylamino group and several pi-acceptor substituents at both terminals of the conjugated system were synthesized by intramolecular [4 + 2] cycloaddition of 1-thio-enynes and subsequent chemical transformations. They displayed largely red-shifted absorption and emission spectra in solution, the powder state, and in polymer films. The derivatives with a 2,2-dicyanoethenyl group as the p-acceptor exhibited inverted solvatochromism in both optical absorption and fluorescence spectroscopies.
• Deciphering the Photophysical Role of Conjugated Diyne in Butadiynyl Fluorophores: Synthesis, Photophysical and Theoretical Study
  作者：Avik Kumar Pati、Monalisa Mohapatra、Pokhraj Ghosh、Santosh J. Gharpure、Ashok K. Mishra

  DOI：10.1021/jp404809g

  日期：2013.8.1

  The present work focuses on the current interest in diyne bridged chromophores necessitating a clearer understanding of the photophysics of such molecules. The significance of the diyne moiety in the photophysics has been investigated by synthesizing simple substituted diphenyl butadiynyl derivatives following a quick and efficient microwave assisted Eglinton coupling of terminal alkynes. Emission of the fluorophores is observed from the usual locally excited (LE) state and intramolecular charge transfer (ICT) state. Separation of pure ICT emission from pure LE emission has been carried out by Gaussian/Lorentzian curve fitting. The vibronic coupling in the local transitions appears to be confined to the normal mode involving the C-C triple bond stretching of the diyne moiety. This implies that the LE transition involves the diyne moiety, a conclusion supported by quantum chemical calculations. The resolved ICT emission follows double linear dependence on E-T(30) solvent polarity scale. The important role of the diyne moiety in the photophysics of this class of molecules is clearly discernible in this study.
• US4703096A
  申请人：——

  公开号：US4703096A

  公开（公告）日：1987-10-27
• US4711532A
  申请人：——

  公开号：US4711532A

  公开（公告）日：1987-12-08