On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins

Inna A. Abdulaeva (1, 2) , Kirill P. Birin (2) , Julien Michalak (1) , Anthony Romieu (3, 1) , Christine Stern (1) , Alla Bessmertnykh-Lemeune (1) , Roger Guilard (1) , Yulia G. Gorbunova (2, 4) , Aslan Yu. Tsivadze (4, 2)

1 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]
2 A.N. Frumkin Institute of Physical Chemistry and Electrochemistry
3 IUF - Institut universitaire de France
4 Kurnakov Institute of General and Inorganic Chemistry

The synthesis of functionalized porphyrins and their conjugates from meso-tetraarylporphyrins through the acylation and the oxidation of beta-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of beta-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form beta-functionalized porphyrins bearing a fused imidazole ring. Under optimized experimental conditions both reactions tolerate various functional groups and afford the products in an appropriate overall yield. The mildness and usefulness of this methodology are illustrated by several examples including the synthesis of porphyrins bearing receptor groups and water-solubilizing moieties.

Mots clés: photoinduced electron-transfer; efficient peripheral functionalization; sensitized solar-cells; water-solubilization; pyrrolic position; alpha-diones; building-blocks; bodipy dyes; systems; coordination

Domaines: Chimie

Inna A. Abdulaeva, Kirill P. Birin, Julien Michalak, Anthony Romieu, Christine Stern, et al.. On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins. New Journal of Chemistry, 2016, 40 (7), pp.5758 - 5774. ⟨10.1039/c5nj03247d⟩. ⟨hal-01427448⟩