A turn-on mode fluorescent diarylethene: Solvatochromism of fluorescence
A turn-on mode fluorescent diarylethene: Solvatochromism of fluorescence
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DOI：
10.1016/j.dyepig.2018.02.016
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发表时间：
2018-06
影响因子：
4.5
通讯作者：
M. Morimoto;Yuta Takagi;Karina Hioki;Tatsuhiro Nagasaka;Hikaru Sotome;S. Ito;H. Miyasaka;M. Irie
中科院分区：
文献类型：
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作者：
M. Morimoto;Yuta Takagi;Karina Hioki;Tatsuhiro Nagasaka;Hikaru Sotome;S. Ito;H. Miyasaka;M. Irie
环境敏感的荧光团已被用作分子探针，以获取微观结构中的物理和化学信息。在这里，我们报告的荧光二芳基乙烯，这是由光照射开关的溶致变色。一种开启模式光开关荧光二芳基乙烯衍生物，（2-乙基-6-（5-甲基噻吩-2-基）-1-苯并噻吩-1，1-二氧化物-3-基）全氟环戊烯（1a）在紫外（UV）光照射下发生环化反应，形成荧光闭环异构体1b。1b响应于溶剂极性而显著改变荧光颜色，例如在正己烷中的绿色，在四氯化碳（CCl 4）中为黄色，在二氯甲烷（CH 2Cl 2）中为橙子，在二甲基亚砜（DMSO）中为红色，并且在这些溶剂中显示出0.6-0.8的高荧光量子产率。荧光溶剂化显色性归因于分子内电荷转移（ICT）特性1b，其由两端的给电子噻吩环和中心的受电子苯并噻吩1，1-二氧化物基团组成。基于Mataga-Lippert作图的分析表明，1bis的激发态和基态的偶极矩相差达12 D。这种具有光开关能力的溶剂化致变色荧光团在生物细胞和材料的微观极性的超分辨荧光成像中具有潜在的应用前景。
Environment-sensitive fluorophores have been used as molecular probes to acquire physical and chemical information in microstructures. Here, we report on solvatochromism of a fluorescent diarylethene, which is switched by photoirradiation. A turn-on mode photoswitchable fluorescent diarylethene derivative, 1,2-bis(2-ethyl-6-(5-methylthiophen-2-yl)-1-benzothiophen-1,1-dioxide-3-yl)perfluorocyclopentene (1a), underwent a cyclization reaction upon irradiation with ultraviolet (UV) light to form fluorescent closed-ring isomer1b.1bdramatically changed the fluorescent color in response to solvent polarity, such as green inn-hexane, yellow in tetrachloromethane (CCl4), orange in dichloromethane (CH2Cl2), and red in dimethyl sulfoxide (DMSO), and showed high fluorescence quantum yields of 0.6–0.8 in these solvents. The fluorescent solvatochromism is ascribed to the intramolecular charge-transfer (ICT) character of1b, which consists of electron-donating thiophene rings at both ends and central electron-accepting benzothiophene 1,1-dioxide groups. The analysis based on the Mataga-Lippert plot revealed that the difference in the dipole moments between the excited and ground states of1bis as large as 12 D. Such a solvatochromic fluorophore with photoswitching ability can find potential applications in super-resolution fluorescence imaging of microscopic polarity in biological cells and materials.