N-Iodosuccinimide-mediated dimerization and macrocyclization of indodicarbocyanine dyes

Abstract

The reaction of indodicarbocyanine dyes with N-iodosuccinimide produces dimeric molecules together with the corresponding meso-iodinated dyes depending on the aryl substitution of the dyes and reaction conditions. Iodinated dyes are more reactive in BF3-catalized dimerization than brominated analogues. Reaction of N-iodosuccinimide with N,N′-connected dimeric pentamethines gave rise to macrocyclic dyes with 16- and 20-membered cycles.