4,5-bis(5-chloro-2-methylthiophen-3-yl)-2-phenyl-1H-imidazole | 1152809-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-bis(5-chloro-2-methylthiophen-3-yl)-2-phenyl-1H-imidazole
• 英文别名: 4,5-Bis(5-chloro-2-methylthiophen-3-yl)-2-phenyl-1H-imidazole
• CAS: 1152809-43-2
• 化学式: C₁₉H₁₄Cl₂N₂S₂
• 分子量: 405.372
• InChiKey: WEQNRHPZPQPHSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-bis(5-chloro-2-methylthiophen-3-yl)-2-phenyl-1H-imidazole 在 air 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以65%的产率得到11,12-Dimethyl-4-phenyl-10,13-dithia-3,5-diazatetracyclo[10.3.0.02,6.07,11]pentadeca-1(15),2(6),3,7-tetraene-9,14-dione
  参考文献：
  名称：

  Synthesis and photophysical properties of thiolactone derivatives

  摘要：

  A class of bis-thiolactone derivatives is prepared by photo-conversion of photochromic diarylethenes with a bis (5-chloro-2-methylthiophen-3-yl) system in moderate yields (50-60%). Bis-thiolactone derivatives show fluorescence in solution with moderate fluorescent quantum yields (0.11-0.17). Reaction mechanism exhibits that the photo-conversion of diarylethenes to bis-thiolactone derivatives undergoes a two-step reaction: photocyclization and photo-oxidation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.057
• 作为产物：
  描述：

  2-氯-5-甲基噻吩 在 吡啶 、 ammonium acetate 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 4,5-bis(5-chloro-2-methylthiophen-3-yl)-2-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and photophysical properties of thiolactone derivatives

  摘要：

  A class of bis-thiolactone derivatives is prepared by photo-conversion of photochromic diarylethenes with a bis (5-chloro-2-methylthiophen-3-yl) system in moderate yields (50-60%). Bis-thiolactone derivatives show fluorescence in solution with moderate fluorescent quantum yields (0.11-0.17). Reaction mechanism exhibits that the photo-conversion of diarylethenes to bis-thiolactone derivatives undergoes a two-step reaction: photocyclization and photo-oxidation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.057

文献信息

• Imidazole diarylethene switches: an alternative to acid-gated photochromism
  作者：Kang-Tai Xiong、Meng-Lian Li、Yue Jiang、Hai-Bing Xu、Ming-Hua Zeng

  DOI：10.1039/d0nj00606h

  日期：——

  We prepared five diarylethenes containing 2-aryl-imidazole as the ethene bridge (L1–L5), and introduced response sites in imidazole rather than in the traditional appended aryl units to regulate their photochromism and thermal stability under acid stimulus. The results show that we can change the thermal stability from P- to T-type, and prevent their photoactivity by acidification, and it is clarified

  我们准备了五个含有2-芳基咪唑作为乙烯桥（L1-L5）的二芳烃，并在咪唑中而不是在传统的附加芳基单元中引入了响应位点，以调节它们在酸刺激下的光致变色和热稳定性。结果表明，我们可以将热稳定性从P型转变为T型，并通过酸化阻止其光活性，并且可以证明，酸越强或添加的酸越多，二芳基乙烯光稳定性的衰减速度越快。此外，可以通过用等摩尔量的碱中和来恢复被禁止的光活性。
• Synthesis of diarylethene derivatives containing various heterocycles and tuning of light-emitting properties in a turn-on fluorescent diarylethene system
  作者：Ziyong Li、Jianlong Xia、Jinhua Liang、Jingjing Yuan、Guojun Jin、Jun Yin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1016/j.dyepig.2011.01.008

  日期：2011.9

  imidazole ring greatly affect the optical properties. The light-emitting properties can be easily tuned from blue light-emitting to yellow light-emitting fluorescence by varying the nature of the heterocycle or by simple modification of structures, which provides a new strategy for the design of novel fluorescent switches. Moreover, Cu2+, Hg2+, and Fe3+ greatly affect the fluorescence properties of diarylethene

  合成了一系列新的引入不同杂环的二芳烃及其N-甲基化衍生物，并通过NMR，MS和元素分析对产物进行了表征。每种化合物在紫外线照射下均表现出光致变色和“开启”荧光特性。已经发现，连接到咪唑环的杂环的性质和咪唑环的甲基化都极大地影响光学性质。通过改变杂环的性质或通过简单的结构修饰，可以容易地将发光性质从发蓝光的荧光调整为发黄光的荧光，这为新颖的荧光开关的设计提供了新的策略。此外，Cu 2 +，Hg2+和Fe 3+在光平稳状态下极大地影响了二芳基乙烯4的荧光性质，因此这些系统可能会部署在新型分子传感器中，以通过荧光识别来检测此类阳离子。