1-(2-methyl-5-(4-methoxyphenyl)-3-thienyl)-2-(2-cyano-1,5-dimethyl-4-pyrryl)hexafluorocyclopentene | 942612-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-methyl-5-(4-methoxyphenyl)-3-thienyl)-2-(2-cyano-1,5-dimethyl-4-pyrryl)hexafluorocyclopentene
• 英文别名: 1-(2-cyano-1,5-dimethyl-4-pyrryl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene；1-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]-2-(2-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene；4-[3,3,4,4,5,5-Hexafluoro-2-[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-1,5-dimethylpyrrole-2-carbonitrile；4-[3,3,4,4,5,5-hexafluoro-2-[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-1,5-dimethylpyrrole-2-carbonitrile
• CAS: 942612-13-7
• 化学式: C₂₄H₁₈F₆N₂OS
• 分子量: 496.476
• InChiKey: SFARYBNCGIDRFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-5-(4-methoxyphenyl)-3-thienyl)-2-(2-cyano-1,5-dimethyl-4-pyrryl)hexafluorocyclopentene 以 正己烷 为溶剂， 生成 8,8,9,9,10,10-Hexafluoro-4-(4-methoxyphenyl)-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：

  具有吡咯单元的异构光致变色二硫杂环丁烷的高效合成和性能。

  摘要：

  已经开发了两种具有吡咯单元的新的异构光致变色二芳基蒽。已经研究了它们的性质，包括光致变色行为，晶体结构和荧光性质。两种异构体化合物在溶液和单晶相中均显示出明显不同的光致变色现象：一种在光环化后变成红色，而另一种变成蓝色，这可能是由于不同的取代基作用所致。

  DOI：

  10.1021/ol070622q
• 作为产物：
  描述：

  1,5-二甲基-2-吡咯甲腈 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 1-(2-methyl-5-(4-methoxyphenyl)-3-thienyl)-2-(2-cyano-1,5-dimethyl-4-pyrryl)hexafluorocyclopentene
  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

• Synthesis and the effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a pyrrole unit
  作者：Gang Liu、Shouzhi Pu、Xiaomei Wang

  DOI：10.1016/j.jphotochem.2010.07.001

  日期：2010.8

  moiety were synthesized, and the structures of two isomeric compounds were determined by single-crystal X-ray diffraction analysis. The properties of these compounds, including photochromism, fluorescence and electrochemical properties of these diarylethenes were also investigated systematically. Each of the four diarylethene derivatives exhibited good photochromism and functioned as an effective fluorescent

  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。
• Efficient Synthesis and Properties of Isomeric Photochromic Diarylethenes Having a Pyrrole Unit
  作者：Shouzhi Pu、Gang Liu、Liang Shen、Jingkun Xu

  DOI：10.1021/ol070622q

  日期：2007.5.1

  Two new isomeric photochromic diarylethenes with a pyrrole unit have been developed. Their properties, including photochromic behavior, crystal structures, and fluorescent properties, have been investigated. The two isomeric compounds show distinctly different photochromism, both in solution and in the single-crystalline phase: one turns red upon photocyclization whereas the other turns blue, which

  已经开发了两种具有吡咯单元的新的异构光致变色二芳基蒽。已经研究了它们的性质，包括光致变色行为，晶体结构和荧光性质。两种异构体化合物在溶液和单晶相中均显示出明显不同的光致变色现象：一种在光环化后变成红色，而另一种变成蓝色，这可能是由于不同的取代基作用所致。
• 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.