European Journal of Organic Chemistry p. 5219 - 5224 (2017)
Update date:2022-08-16
Topics:
Baleeva, Nadezhda S.
Zaitseva, Snezhana O.
Gorbachev, Dmitriy A.
Smirnov, Alexander Yu.
Zagudaylova, Marina B.
Baranov, Mikhail S.
We report the creation of a novel group of the ABDI-BF2 fluorescent dyes based on the conformationally locked GFP chromophore. We studied the intramolecular mechanism of radiationless deactivation of the ABDI-BF2 fluorophore by introducing the various substituents at the nitrogen atom. The results of this study and our previous work allowed us to claim that in case of ABDI-BF2 this deactivation is determined by the formation of the nonfluorescent internal charge transfer exited state with a planar quinoidal structure. The electronic effects have a greater impact on the radiationless deactivation than the conformation. Thus, the introduction of an electron-donating group is more effective than the creation of rigid derivatives. The presented dyes are characterized by high fluorescence quantum yields and pH-independence in the physiological pH range, making them promising candidates for a wide spectrum of fluorescence labeling applications.
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