A tetrazole-ene photoactivatable fluorophore with improved brightness and stability in protic solution

Abstract

The pyrazoline fluorophore, generated by photoinduced tetrazole-ene cycloaddition, shows faint fluorescence in protic solvents. To suppress this fluorescence-quenching, we rationally designed a series of substituted diaryl tetrazoles at the N-side phenyl ring to produce a tetrazole-ene based photoactivatable fluorophore. Spectroscopic and cellular imaging studies demonstrated that the version of the fluorophore with a bis(trifluoromethyl)benzene substituent exhibited significantly enhanced brightness and photostability.