Design of an efficient charge-transfer processing molecular system containing a weak electron donor: spectroscopic and redox properties and cation-induced fluorescence enhancement

The acceptor strength of the boron-dipyrromethene chromophore in directly linked donor–acceptor compounds can be tuned by substituents in such a way that a fast excited state charge transfer takes place even for the comparatively weak benzo crown electron donor. This leads to strong fluorescence quenching. Upon binding of cations (Na+ and K+) to the benzo crown receptor, the donor properties of the latter are further reduced, partly suppressing charge transfer. Large fluorescence enhancement factors and cation-selective fluorescence decay times result which are the basis for improved analytical application of these dyes as highly sensitive fluorescent probes.