The role of N-substituents in radiationless deactivation of aminated derivatives of locked GFP chromophore

We report the creation of novel group of the ABDI-BF2 fluorescent dyes based on the conformationally locked GFP chromophore. We studied the intramolecular mechanism of radiationless deactivation of 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 non-fluorescent internal charge transfer exited state with a planar quinoidal structure. The electronic effects have a greater impact on the radiationless deactivation than conformational. Thus, the electron-donating group introduction is more effective then the rigid-derivatives creation. 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 fluorescent labeling applications.

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