1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-phenyl-3-thienyl]perfluorocyclopentene | 1272601-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-phenyl-3-thienyl]perfluorocyclopentene
• 英文别名: 1-(2-cyano-1,5-dimethyl-4-pyrryl)-2-[2-methyl-5-phenyl-3-thienyl]perfluorocyclopentene；1-(2-methyl-5-phenyl-3-thienyl)-2-(2-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene；1-[2-methyl-5-phenyl-3-thienyl]-2-(2-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene；4-[3,3,4,4,5,5-Hexafluoro-2-(2-methyl-5-phenylthiophen-3-yl)cyclopenten-1-yl]-1,5-dimethylpyrrole-2-carbonitrile
• CAS: 1272601-83-8
• 化学式: C₂₃H₁₆F₆N₂S
• 分子量: 466.45
• InChiKey: GDLKPESGOHECQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-phenyl-3-thienyl]perfluorocyclopentene 以 正己烷 为溶剂， 生成 8,8,9,9,10,10-Hexafluoro-1,2,15-trimethyl-4-phenyl-3-thia-15-azatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraene-14-carbonitrile
  参考文献：
  名称：

  取代基位置的合成及其对带有吡咯单元的不对称异构二芳烃的影响

  摘要：

  合成了四个带有吡咯部分的不对称二芳烃，并通过单晶X射线衍射分析确定了两种异构体的结构。还系统地研究了这些化合物的性质，包括这些二芳烃的光致变色，荧光和电化学性质。四种二芳基乙烯衍生物中的每一种均表现出良好的光致变色性，并且在溶液和PMMA膜中均起有效的荧光光开关作用。当在末端苯环的三个位置上的任何一个上连接甲氧基时，最大吸收率，环化和环还原的量子产率以及开环异构体的荧光量子产率增加，而发射峰明显减少。与带有吡唑部分的类似二芳烃相比，吡咯部分的引入可以增加吸收最大值，并显着降低环回复量子产率。循环伏安图证实，甲氧基及其取代位置可有效调节这些二芳基乙烯衍生物的电化学行为。

  DOI：

  10.1016/j.jphotochem.2010.07.001
• 作为产物：
  描述：

  8,8,9,9,10,10-Hexafluoro-1,2,15-trimethyl-4-phenyl-3-thia-15-azatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraene-14-carbonitrile 以 正己烷 为溶剂， 生成 1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-phenyl-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  取代基位置的合成及其对带有吡咯单元的不对称异构二芳烃的影响

  摘要：

  合成了四个带有吡咯部分的不对称二芳烃，并通过单晶X射线衍射分析确定了两种异构体的结构。还系统地研究了这些化合物的性质，包括这些二芳烃的光致变色，荧光和电化学性质。四种二芳基乙烯衍生物中的每一种均表现出良好的光致变色性，并且在溶液和PMMA膜中均起有效的荧光光开关作用。当在末端苯环的三个位置上的任何一个上连接甲氧基时，最大吸收率，环化和环还原的量子产率以及开环异构体的荧光量子产率增加，而发射峰明显减少。与带有吡唑部分的类似二芳烃相比，吡咯部分的引入可以增加吸收最大值，并显着降低环回复量子产率。循环伏安图证实，甲氧基及其取代位置可有效调节这些二芳基乙烯衍生物的电化学行为。

  DOI：

  10.1016/j.jphotochem.2010.07.001

文献信息

• The effect of the cyano group position upon unsymmetrical isomeric diarylethenes bearing a pyrrole unit
  作者：Gang Liu、Shouzhi Pu、Xiaomei Wang、Weijun Liu、Congbin Fan

  DOI：10.1016/j.dyepig.2010.12.007

  日期：2011.8

  Four photochromic diarylethenes bearing a pyrrole moiety were synthesized, and the structures of two of the new isomeric compounds were determined by single-crystal X-ray diffraction analysis. Each of the diarylethene derivatives exhibited good photochromism both in solution and in poly(methyl methacrylate) films, which their photoconversion ratios from open-ring to closed-ring isomers were larger

  合成了四个带有吡咯部分的光致变色二蒽，并通过单晶X射线衍射分析确定了两种新的异构化合物的结构。每种二芳基乙烯衍生物在溶液和聚甲基丙烯酸甲酯薄膜中均表现出良好的光致变色性，在光固定态下，它们在己烷中从开环异构体到闭环异构体的光转化率大于89％。它们在己烷和聚甲基丙烯酸甲酯薄膜中也起有效的荧光光电开关的作用。当氰基连接在末端苯环的三个位置中的任何一个位置上时，最大吸收，环化/环还原量子产率和荧光量子产率增加，而摩尔吸收系数和发射峰显着降低。循环伏安图表明氰基的引入降低了开环异构体的带隙而增加了闭环异构体的带隙。氰基及其取代位置可有效地调节这些二芳基乙烯衍生物的光学和电化学行为。
• Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety
  作者：Gang Liu、Shouzhi Pu、Xiaomei Wang、Weijun Liu、Tianshe Yang

  DOI：10.1016/j.dyepig.2010.11.001

  日期：2011.7

  Five diarylethenes bearing a pyrrole moiety were synthesized in order to investigate the effects of the substituents on the properties of these compounds. The structures of three of the diarylethenes were determined by single-crystal X-ray diffraction analysis. All of the diarylethene derivatives exhibited notable photochromism and functioned as effective fluorescent photo-switches in solution and in poly (methyl methacrylate) films. The absorption maxima and the quantum yields of cyclization and cyclo-reversion increased whereas the emission peaks and the emission intensities decreased evidently when the electron-withdrawing/donating substituent was attached at the para-position on the terminal benzene ring. Cyclic voltammograms indicated that the electron-withdrawing/donating substituents decreased the bang gaps of the open-ring isomers but enhanced those of the closed-ring isomers, compared with the unsubstituted parent diarylethene. The properties of these diarylethene derivatives were significantly different from each other, which might be attributed to the different substituent effects. (C) 2010 Elsevier Ltd. All rights reserved.
• The effect of the fluorine atom position upon isomeric photochromic diarylethenes bearing a pyrrole unit
  作者：Gang Liu、Shouzhi Pu、Bing Chen

  DOI：10.1016/j.jphotochem.2013.04.023

  日期：2013.7

  A new class of isomeric diarylethenes bearing a pyrrole moiety have been synthesized, and their properties including photochromism, fluorescence, and electrochemical properties have been discussed systematically. Each of the diarylethenes exhibited evident photochromism and functioned as a remarkable fluorescent switch in both solution and PMMA films. Their photoconversion ratios were larger than 90%, and the fluorescent modulation efficiencies were greater than 88% in the photostationary state. The absorption maxima, quantum yields of cyclization and cycloreversion, and band-gaps of the closed-ring isomers increased whereas the emission intensity and band-gaps of the open-ring isomers greatly decreased when the fluorine atom was attached at any of the three positions on the terminal benzene ring. Cyclic voltammograms suggested that the oxidation onsets and band-gaps of the open-ring isomers were much bigger than those of the closed-ring isomers. The fluorine atom and its substituted position could availably modulate their optical and electrochemical behaviors. (C) 2013 Elsevier B.V. All rights reserved.