1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene | 1272601-86-1

• 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-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene
• 英文别名: 1-[2-methyl-5-(4-cyanophenyl)-3-thienyl]-2-(2-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene；4-[2-[5-(4-Cyanophenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-1,5-dimethylpyrrole-2-carbonitrile；4-[2-[5-(4-cyanophenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]-1,5-dimethylpyrrole-2-carbonitrile
• CAS: 1272601-86-1
• 化学式: C₂₄H₁₅F₆N₃S
• 分子量: 491.46
• InChiKey: WDXUDGUPTBFUHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-cyano-1,5-dimethyl-4-pyrrolyl)-2-[2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene 以 正己烷 为溶剂， 生成 4-(4-Cyanophenyl)-8,8,9,9,10,10-hexafluoro-1,2,15-trimethyl-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：

  Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

  摘要：

  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.

  DOI：

  10.1016/j.dyepig.2010.11.001
• 作为产物：
  描述：

  4-(4-Cyanophenyl)-8,8,9,9,10,10-hexafluoro-1,2,15-trimethyl-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-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

  摘要：

  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.

  DOI：

  10.1016/j.dyepig.2010.11.001

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。