Nucleosides as organizing agents

Abstract

In the present review, we discuss the results of the research we have done over the last decade on multi-porphyrinic architectures bearing a nucleotidic backbone, compare all the data, offer a novel overview, and emphasize common capabilities of nucleosides appearing in various systems, providing a new insight on the pre-organizing capabilities of nucleosidic backbones. The efficiency of nucleosides as pre-organizing agents was investigated through the synthesis and study of various bis-porphyrins bearing nucleosidic linkers, as well as through the investigation of the conformation of linear and arborescent multi-porphyrins constructed on a nucleosidic backbone. The capacity of these molecules to complex guests with a high association constant was used as a tool to evaluate their degree of pre-organization, as well as the investigation of the electronic coupling existing between their chromophores and their photo-chemical capacities. Such an overview of one decade of scientific investigations documents the fact that rigid linkers between chromophores are not necessary for their spatial pre-organization, opening new routes to the faster synthesis of flexible highly pre-organized molecular architectures avoiding the long and tedious synthesis of rigid tweezers, especially for the preparation of rigid linkers which may bring solubility and stability problems.