Proton-induced fluorescence switching in novel naphthalimide-dansylamide dyads

J Org Chem. 2005 Dec 9;70(25):10565-8. doi: 10.1021/jo0512195.

Abstract

[reaction: see text] Three novel bichromophoric dyads containing dansylamide and 1,8-naphthalimide linked by oligomethylene spacers of varying length were prepared. The fluorescent moiety can be reversibly selected by protonation/deprotonation of the dansyl residue via control of singlet-singlet energy transfer and photoinduced electron transfer, leading to a molecular optical switch with two spectrally distinguished "on" states.