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RESEARCH PRODUCT
On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins
Aslan Yu. TsivadzeInna A. AbdulaevaInna A. AbdulaevaAnthony RomieuAnthony RomieuYulia G. GorbunovaChristine SternJulien MichalakRoger GuilardKirill P. BirinAlla Bessmertnykh-lemeunesubject
coordination010402 general chemistryRing (chemistry)01 natural sciences[ CHIM ] Chemical SciencesCatalysisphotoinduced electron-transferAcylationchemistry.chemical_compoundMaterials Chemistrypolycyclic compoundsImidazoleOrganic chemistry[CHIM]Chemical Sciencesalpha-dionesbuilding-blockspyrrolic position010405 organic chemistrysensitized solar-cellsbodipy dyesGeneral Chemistryefficient peripheral functionalizationCondensation reactionCombinatorial chemistryPorphyrin0104 chemical scienceswater-solubilizationchemistryYield (chemistry)systemsAmmonium acetateConjugatedescription
International audience; 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-02-04 |