Reversible Fluorescence Switching of Donor–Acceptor Type Bipyridines by Simple Protonation–Deprotonation Equilibria

Abstract

This article describes the switchable fluorescence of a series of donor–acceptor type 2,2′-bipyridines. The original bipyridine molecules have four protonation sites – two on the amino donor sites and two on the pyridine acceptor cores. These nitrogen-containing sites are selectively protonated by suitable acids and the protonation influences the electronic conjugation and structure of the chromophores. Consequently, the emission characteristics of the molecules are affected, and this behaviour is reversible, i.e. the neutral original species are regenerated by the addition of an equivalent amount of base. The switchable behaviour of these compounds is accompanied by a visible colour change of the relevant solutions.