Turn-on mode fluorescent diarylethenes: effect of electron-donating and electron-withdrawing substituents on photoswitching performance
Turn-on mode fluorescent diarylethenes: effect of electron-donating and electron-withdrawing substituents on photoswitching performance
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DOI：
10.1039/d0pp00064g
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发表时间：
2020-06-01
影响因子：
3.1
通讯作者：
Irie, Masahiro
中科院分区：
文献类型：
--
作者：
Iwai, Ryota;Morimoto, Masakazu;Irie, Masahiro
具有苯并噻吩S，S-二氧化物基团的二芳基乙烯衍生物经历开启模式荧光光开关。对于超分辨率荧光显微镜的实际应用，期望光可切换荧光分子能够抵抗光降解。在这里，我们合成了在苯并噻吩S，S-二氧化物基团的6-和6 '-位的苯环上具有吸电子（三氟甲基或硝基）或供电子（甲基，甲氧基或二甲氨基）取代基的开启模式荧光二芳基乙烯，并检查了取代基对光开关性能的影响。具有供电子取代基的衍生物的吸收光谱和荧光光谱显示出显着的红移。吸电子取代基的引入提高了环化反转量子产率，而给电子取代基的引入降低了环化反转量子产率。引入给电子取代基可显著提高荧光二芳基乙烯在连续紫外光照射下的抗疲劳性能。这种高度抗疲劳的荧光二芳基乙烯可用于超分辨率荧光成像或单分子荧光跟踪。
Diarylethene derivatives having benzothiophene S,S-dioxide groups undergo turn-on mode fluorescence photoswitching. For the practical application to super-resolution fluorescence microscopy, photoswitchable fluorescent molecules are desired to be resistant against photodegradation. Here we synthesized turn-on mode fluorescent diarylethenes having electron-withdrawing (trifluoromethyl or nitro) or electron-donating (methyl, methoxy, or dimethylamino) substituents on phenyl rings at 6- and 6'-positions of the benzothiophene S,S-dioxide groups and examined the effect of the substituents on the photoswitching performance. The derivatives having electron-donating substituents showed significant bathochromic shifts of the absorption and fluorescence spectra. The cycloreversion quantum yield was increased by introducing electron-withdrawing substituents, while it was decreased by the electron-donating ones. Introduction of electron-donating substituents was found to remarkably improve the fatigue resistance of the fluorescent diarylethene under continuous ultraviolet (UV) irradiation. Such highly fatigue-resistant fluorescent diarylethenes are useful for super-resolution fluorescence imaging or single-molecule fluorescence tracking.