From biology to nanomaterials: Nucleosides, a powerful spatial organizing backbone in multi-porphyrinic arrays

Controlling the orientation of chromophores in space is a great challenge of modern chemistry. We highlight in the present review, the capability of nucleosides to confer blocked conformation to multi-porphyrinic architectures and thus behave as organizing agents. At first, various nucleosides were functionalized by two porphyrins. Two arborescent multi-porphyrins bearing nucleosidic linkers were then prepared. In these ramified molecular architectures, 4 or 8 Zn(II) porphyrins surround a central free-base porphyrinic core. A linear oligonucleoside with pendant porphyrins was also synthesized. The capacity of these compounds to complex guests was used as a tool to evaluate their degree of preorganization, as well as the investigation of the electronic coupling existing between their chromophores and their photo-chemical capacities. Rigid spacers do not seem to be anymore the only choice for the organization of molecular architectures. Well-chosen nucleosidic moieties can act as great pre-organizing agents and offer an interesting option for the synthesis of organized multi-porphyrinic devices. The chirality and enantio-purity of the nucleosidic linkers also pave the way toward the selective complexation of enantio-pure bidentate guests and the resolution of racemates.