[2-methyl-5-(p-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene | 1374693-92-1

• 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: [2-methyl-5-(p-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene
• 英文别名: [2-methyl-5-(4-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene；2-methyl-3-(perfluorocyclopent-1-en-1-yl)-5-(4-(trifluoromethyl)phenyl)thiophene；3-(2,3,3,4,4,5,5-Heptafluorocyclopenten-1-yl)-2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene；3-(2,3,3,4,4,5,5-heptafluorocyclopenten-1-yl)-2-methyl-5-[4-(trifluoromethyl)phenyl]thiophene
• CAS: 1374693-92-1
• 化学式: C₁₇H₈F₁₀S
• 分子量: 434.301
• InChiKey: NRAMTWBYYXLPNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-溴-2,4-二甲氧基嘧啶 、 [2-methyl-5-(p-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以47%的产率得到1-(2,4-dimethoxyl-5-pyrimidinyl)-2-[2-methyl-5-(p-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  具有嘧啶部分的新的光致变色二芳烃

  摘要：

  首次合成了基于六元嘧啶和五元噻吩部分杂化骨架的一类新型光致变色二芳基乙烯衍生物。已经系统地研究了取代基对其性能的影响，包括光致变色，抗疲劳性和荧光性。所有这些二芳烃在溶液和聚（甲基丙烯酸甲酯）薄膜中均显示出显着的光致变色性和显着的荧光转换特性。给电子取代基提高了其环化量子产率，抗疲劳性和荧光量子产率，而吸电子基团表现出相反的作用。

  DOI：

  10.1016/j.tetlet.2012.11.141
• 作为产物：
  描述：

  4-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 17.5h， 生成 [2-methyl-5-(p-trifluoromethylphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  具有喹啉部分的新的不对称二芳烃的光致变色

  摘要：

  合成了三个具有6元喹啉部分的不对称二芳烃，以研究取代基对其光致变色和荧光的影响，并通过单晶X射线衍射分析确定了一种二芳基乙烯的结构。喹啉直接作为芳基部分连接至中央全氟环戊烯环，可用于在溶液，无定形膜和结晶相中参与光异构化反应。这些二芳烃具有良好的光致变色性，具有出色的热稳定性和明显的抗疲劳性。给电子的甲氧基可提高闭环异构体的最大吸收量，并提高环化和环还原的量子产率，但吸电子三氟甲基的作用相反。此外，它们在溶液和聚甲基丙烯酸甲酯薄膜中均起着显着的荧光开关的作用，三氟甲基和甲氧基均增加了发射强度。结果表明，喹啉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：

  10.1002/poc.3716

文献信息

• Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
  作者：Sebastian Fredrich、Aurelio Bonasera、Virginia Valderrey、Stefan Hecht

  DOI：10.1021/jacs.8b02982

  日期：2018.5.23

  Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular

  在光诱导异构化后，带有反应性醛部分的二芳基乙烯 (DAE) 在胺存在下选择性地重排，并伴有脱色。在一项综合研究中，探针结构根据其在亲核试剂触发的重排反应中的固有反应性进行了优化。可以推导出详细的结构-反应关系，特别是关于整合（杂）芳基部分的类型以及甲酰基残基的位置，并且优化了探针与伯胺和仲胺的固有反应性。利用辅助碱基，最初形成的重排产物可以参与随后的催化循环，导致放大的脱色过程。这种额外的催化途径使我们能够提高我们方法的灵敏度并成功区分胺和硫醇。此外，已设计出表现出强分析物诱导荧光调制的探针，以通过使用更灵敏的读数进一步降低检测限。优化的 DAE 探针是未来可编程传感材料和设备的有前途的分子组件。
• 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。
• New photochromic diarylethenes with a pyrimidine moiety
  作者：Hongliang Liu、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.tetlet.2012.11.141

  日期：2013.2

  A novel class of photochromic diarylethene derivatives based on the hybrid skeleton of six-membered pyrimidine and five-membered thiophene moieties has been firstly synthesized. The substituent effects on their properties, including photochromism, fatigue resistance, and fluorescence, have been systematically investigated. All these diarylethenes showed significant photochromism and notable fluorescence

  首次合成了基于六元嘧啶和五元噻吩部分杂化骨架的一类新型光致变色二芳基乙烯衍生物。已经系统地研究了取代基对其性能的影响，包括光致变色，抗疲劳性和荧光性。所有这些二芳烃在溶液和聚（甲基丙烯酸甲酯）薄膜中均显示出显着的光致变色性和显着的荧光转换特性。给电子取代基提高了其环化量子产率，抗疲劳性和荧光量子产率，而吸电子基团表现出相反的作用。
• Photochromism of new unsymmetrical diarylethenes with an indazole moiety
  作者：Jingjing Liu、Hongliang Liu、Shouzhi Pu

  DOI：10.1016/j.tetlet.2015.07.052

  日期：2015.9

  A new class of photochromic diarylethenes with an indazole moiety has been firstly synthesized, and their photochromic and fluorescence properties have been investigated. The indazole moiety was connected directly to the central cyclopentene ring as one heteroaryl unit and availably participated in the photoinduced cyclization reaction in solution, amorphous film, as well as in the crystalline phase. These diarylethenes exhibited excellent photochromism with good thermal stability and remarkable fatigue resistance. They also functioned as notable fluorescence switches in both solution and amorphorous films. In addition, the different substituents at the para-position of the terminal benzene ring had a significant effect on their properties: the electron-donating methoxy group could enhance the quantum yields of cyclization and cycloreversion and fluorescence quantum yield, but the electron-withdrawing trifluoromethyl had opposite effect. (C) 2015 Elsevier Ltd. All rights reserved.
• Photochromism of asymmetrical diarylethenes with a pyrimidine unit: Synthesis and substituent effects
  作者：Hongliang Liu、Shouzhi Pu、Gang Liu、Bing Chen

  DOI：10.1016/j.dyepig.2013.10.047

  日期：2014.3

  Five photochromic diarylethenes with a six-membered pyrimidine moiety were synthesized to investigate the effects of the substituents on their photochromic behaviors, and the structures of four of the diarylethenes were determined by single-crystal X-ray diffraction analysis. The pyrimidine moiety was connected directly to the central cyclopentene ring as an aryl moiety to participate the photoisomerization reaction in solution, solid amorphous films, and crystalline phase. All of the diarylethene derivatives showed favorable photochromism and functioned as notable fluorescent photo-switches in both solution and solid media. The electron-donating substituents enhanced their cyclization quantum yields, fatigue resistance, and fluorescence quantum yields, whereas the electron-withdrawing groups exerted inversed actions on the diarylethenes. The results revealed that the pyrimidine moiety and substituents played a very important role during the process of photoisomerization reactions. (C) 2013 Elsevier Ltd. All rights reserved.