3-(4-dimethylamino-phenyl)-2-(4-phenyl-thiazol-2-yl)-acrylonitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-dimethylamino-phenyl)-2-(4-phenyl-thiazol-2-yl)-acrylonitrile
• 英文别名: 3-[4-(Dimethylamino)phenyl]-2-(4-phenyl-1,3-thiazol-2-yl)prop-2-enenitrile
• 化学式: C₂₀H₁₇N₃S
• mdl: MFCD00386293
• 分子量: 331.441
• InChiKey: MIWYYFNEORSTDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 2-(4-苯基-1,3-噻唑-2-基)乙腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 3-(4-dimethylamino-phenyl)-2-(4-phenyl-thiazol-2-yl)-acrylonitrile
  参考文献：
  名称：

  Schaefer,H.; Gewald,K., Journal fur praktische Chemie (Leipzig 1954), 1974, vol. 316, p. 684 - 692

  摘要：

  DOI：

文献信息

• 3-Aryl-2-(thiazol-2-yl)acrylonitriles assembled with aryl/hetaryl rings: Design of the optical properties and application prospects
  作者：Alexander K. Eltyshev、Timur H. Dzhumaniyazov、Polina O. Suntsova、Artem S. Minin、Varvara A. Pozdina、Wim Dehaen、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2020.108836

  日期：2021.1

  New fluorescent thiazoles were designed and synthesized based on a 3-aryl-2-(thiazol-2-yl)acrylonitrile core. Three synthetic approaches were developed to introduce specific combinations of substituents at the 2-, 4- and 5-thiazole positions. The obtained thiazolyl-2-acrylonitriles exhibited a wide range of fluorescent colours (from green to red), long wavelength maxima and intensity depending on the combination of the substituents located at rings A, B and C. The expanded photophysical investigation established the best substituent combinations to increase their emission. Absorption and emission were studied in solvents with different polarities, as well as in DMSO-water and dioxane-water mixtures. The thiazoles showed multifunctional properties and exhibited good emission in the solid phase and in suspension (aggregation induced enhancement emission/AIEE effect). Photophysical investigations revealed a large Stokes shift, significant positive solvatochmmism, and the tunability of the colour and intensity. Sharp strengthening of the emission intensity of the thiazoles was observed upon stimulation with some acid (H2SO4 and BF3 center dot OEt2) in solvents and in the solid phase (HCl). State-of-the-art quantum mechanical calculations were performed to interpret the experimental findings. Biological experiments revealed the good penetration of the thiazoles into living cells and the accumulation both in lysosomes and, to a lesser extent, near membranes.
• Schaefer,H.; Gewald,K., Journal fur praktische Chemie (Leipzig 1954), 1974, vol. 316, p. 684 - 692
  作者：Schaefer,H.、Gewald,K.

  DOI：——

  日期：——