1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene | 1592847-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene
• 英文别名: 3-[3,3,4,4,5,5-Hexafluoro-2-[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-1,2-dimethylpyrrolo[2,3-b]pyridine；3-[3,3,4,4,5,5-hexafluoro-2-[5-(4-methoxyphenyl)-2-methylthiophen-3-yl]cyclopenten-1-yl]-1,2-dimethylpyrrolo[2,3-b]pyridine
• CAS: 1592847-98-7
• 化学式: C₂₆H₂₀F₆N₂OS
• 分子量: 522.514
• InChiKey: OPQZYIYZPHMSON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene 生成 8,8,9,9,10,10-Hexafluoro-4-(4-methoxyphenyl)-1,2,19-trimethyl-3-thia-17,19-diazapentacyclo[10.7.0.02,6.07,11.013,18]nonadeca-4,6,11,13(18),14,16-hexaene
  参考文献：
  名称：

  Synthesis and photochromism of novel unsymmetrical diarylethenes with an azaindole unit

  摘要：

  A new class of unsymmetrical photochromic diarylethenes with an azaindole moiety has been firstly synthesized. Their properties, including photochromism, crystal structure, as well as fluorescence, were investigated systematically. The azaindole was connected directly to the central cyclopentene ring as a heteroaryl moiety and available to participate in the photoisomerization reaction. Each of the diarylethenes exhibited favorable photochromism, good thermal stability, remarkable fatigue resistance, and notable fluorescence switches in both solution and solid media. The substituents at the para-position of the terminal benzene ring affected evidently their properties: the electron-donating methoxy could be effective to enhance the cyclization quantum yield, while the electron-withdrawing cyano could shift the absorption maximum to a longer wavelength in both hexane and solid film. The results revealed that the introduction of azaindole moieties and different substituents played an important role in the photoisomerization process of these diarylethenes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.004
• 作为产物：
  描述：

  7-氮杂吲哚 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 苄基三乙基氯化铵 、 sodium hydride 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 1-(1,2-dimethyl-7-azaindol-3-yl)-2-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  氮杂吲哚和噻吩部分杂化的新型不对称二芳烃的光致变色

  摘要：

  合成了一类新的同时具有氮杂吲哚和噻吩基团的光致变色二蒽，以研究取代基对其光致变色行为的影响，并通过单晶X射线衍射分析确定其结构。氮杂吲哚部分作为杂芳基部分直接连接到中央环戊烯环上，以参与溶液，固体无定形薄膜和单晶相中的光异构化反应。每个二芳烃在溶液和固体介质中均显示出显着的荧光光开关。给电子的取代基显着提高了其环化量子产率，而吸电子基团大大提高了其闭环异构体的摩尔吸收系数。循环伏安法研究表明，当从给电子取代基转变为吸电子取代基时，带有氮杂吲哚的二芳烃的带隙显着增加。结果表明，氮杂吲哚部分和取代基在这些二芳烃的光异构化反应过程中起着至关重要的作用。

  DOI：

  10.1016/j.dyepig.2014.03.003

文献信息

• Photochromism of new unsymmetrical diarylethenes based on the hybrid of azaindole and thiophene moieties
  作者：Zhiyuan Sun、Hui Li、Gang Liu、Congbin Fan、Shouzhi Pu

  DOI：10.1016/j.dyepig.2014.03.003

  日期：2014.7

  A new class of photochromic diarylethenes with both azaindole and thiophene moieties were synthesized to investigate the effects of the substituents on their photochromic behaviors, and their structures were determined by single crystal X-ray diffraction analysis. The azaindole moiety was connected directly to the central cyclopentene ring as a heteroaryl moiety to participate the photoisomerization

  合成了一类新的同时具有氮杂吲哚和噻吩基团的光致变色二蒽，以研究取代基对其光致变色行为的影响，并通过单晶X射线衍射分析确定其结构。氮杂吲哚部分作为杂芳基部分直接连接到中央环戊烯环上，以参与溶液，固体无定形薄膜和单晶相中的光异构化反应。每个二芳烃在溶液和固体介质中均显示出显着的荧光光开关。给电子的取代基显着提高了其环化量子产率，而吸电子基团大大提高了其闭环异构体的摩尔吸收系数。循环伏安法研究表明，当从给电子取代基转变为吸电子取代基时，带有氮杂吲哚的二芳烃的带隙显着增加。结果表明，氮杂吲哚部分和取代基在这些二芳烃的光异构化反应过程中起着至关重要的作用。
• Synthesis and photochromism of novel unsymmetrical diarylethenes with an azaindole unit
  作者：Zhiyuan Sun、Hui Li、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.tetlet.2014.03.004

  日期：2014.4

  A new class of unsymmetrical photochromic diarylethenes with an azaindole moiety has been firstly synthesized. Their properties, including photochromism, crystal structure, as well as fluorescence, were investigated systematically. The azaindole was connected directly to the central cyclopentene ring as a heteroaryl moiety and available to participate in the photoisomerization reaction. Each of the diarylethenes exhibited favorable photochromism, good thermal stability, remarkable fatigue resistance, and notable fluorescence switches in both solution and solid media. The substituents at the para-position of the terminal benzene ring affected evidently their properties: the electron-donating methoxy could be effective to enhance the cyclization quantum yield, while the electron-withdrawing cyano could shift the absorption maximum to a longer wavelength in both hexane and solid film. The results revealed that the introduction of azaindole moieties and different substituents played an important role in the photoisomerization process of these diarylethenes. (C) 2014 Elsevier Ltd. All rights reserved.