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

• Published in: New journal of chemistry Vol. 40; no. 7; pp. 5758 - 5774
• Main Authors: Abdulaeva, Inna A., Birin, Kirill P., Michalak, Julien, Romieu, Anthony, Stern, Christine, Bessmertnykh-Lemeune, Alla, Guilard, Roger, Gorbunova, Yulia G., Tsivadze, Aslan Yu
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2016; Royal Society of Chemistry [1987-....]
• Subjects: Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; WATER-SOLUBILIZATION; BODIPY DYES; SENSITIZED SOLAR-CELLS; PHOTOINDUCED ELECTRON-TRANSFER; EFFICIENT PERIPHERAL FUNCTIONALIZATION; BUILDING-BLOCKS; PYRROLIC POSITION; SYSTEMS; COORDINATION; ALPHA-DIONES; photoinduced electron-transfer; alpha-diones; building-blocks; systems; sensitized solar-cells; bodipy dyes; efficient peripheral functionalization; water-solubilization; pyrrolic position; coordination
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c5nj03247d

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.