Emission behavior of perimidine attached BODIPY and its response to acid/base.

A BODIPY based with perimidine attached derivative was developed and characterized. It was efficiently synthesized by condensation between aldehyde sited at β-position of BODIPY and 1,8-diamino-naphthalene. Owing to the electron-donor effect of N in heterocycle, emission was quenched completely. Upon protonation of N, the solution exhibited dramatic emission enhancement with emission peak locating at 510 nm, which is estimated to be 275-fold of initial emission. With OH−addition, it could be reverted to the emission to non-emisison state again and establish a fluorescence switch. The underlying mechanism of fluorescence “off-on” is based on the intramolecular PET, which was attested by quantum chemistry calculation approach. [ABSTRACT FROM PUBLISHER]