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Turn-on mode fluorescent diarylethenes: effect of electron-donating and electron-withdrawing substituents on photoswitching performance.
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2020-05-07 , DOI: 10.1039/d0pp00064g Ryota Iwai 1 , Masakazu Morimoto 1 , Masahiro Irie 1
Photochemical & Photobiological Sciences ( IF 2.7 ) Pub Date : 2020-05-07 , DOI: 10.1039/d0pp00064g Ryota Iwai 1 , Masakazu Morimoto 1 , Masahiro Irie 1
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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.
中文翻译：
开启模式荧光二芳基乙烯：给电子和吸电子取代基对光开关性能的影响。
具有苯并噻吩S 、 S-二氧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，需要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 -二氧化物的 6- 和 6'-位苯环上具有吸电子（三氟甲基或硝基）或给电子（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基团并检查取代基对光开关性能的影响。具有供电子取代基的衍生物显示出吸收和荧光光谱的显着红移。引入吸电子取代基可提高环化量子产率，而引入供电子取代基则降低环化量子产率。研究发现，供电子取代基的引入可以显着提高荧光二芳基乙烯在连续紫外线（UV）照射下的抗疲劳性。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。
更新日期：2020-05-07
中文翻译：
开启模式荧光二芳基乙烯：给电子和吸电子取代基对光开关性能的影响。
具有苯并噻吩S 、 S-二氧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，需要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 -二氧化物的 6- 和 6'-位苯环上具有吸电子（三氟甲基或硝基）或给电子（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基团并检查取代基对光开关性能的影响。具有供电子取代基的衍生物显示出吸收和荧光光谱的显着红移。引入吸电子取代基可提高环化量子产率，而引入供电子取代基则降低环化量子产率。研究发现，供电子取代基的引入可以显着提高荧光二芳基乙烯在连续紫外线（UV）照射下的抗疲劳性。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。
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