Four melanin polymers prepared from different precursors (5,6-dihydroxyindole, 5,6-dihydroxyindole 2-carboxylic acid, 1,8-dihydroxynaphthalene and dopamine) have been adopted as photocatalysts in the reductive dehalogenation of a series of model α-halogen carbonyl derivatives. The best performing melanin was that obtained from 5,6-dihydroxyindole 2-carboxylic acid, which allowed to dehalogenate efficiently both bromomalonate esters and phenacyl bromide; on the other hand, chloromalonate esters were almost unreactive under the same reaction conditions. Electrochemical and control experiments enabled to elucidate the reaction mechanism, demonstrating the key role of electrons as charge carriers in the observed photocatalytic process.
Exploring the Reactivity of Melanins as Photocatalysts for Reductive Dehalogenations
Andrea Capucciati;Valentina Foli;Elena Cassera;Daniele Merli;Davide Ravelli
2024-01-01
Abstract
Four melanin polymers prepared from different precursors (5,6-dihydroxyindole, 5,6-dihydroxyindole 2-carboxylic acid, 1,8-dihydroxynaphthalene and dopamine) have been adopted as photocatalysts in the reductive dehalogenation of a series of model α-halogen carbonyl derivatives. The best performing melanin was that obtained from 5,6-dihydroxyindole 2-carboxylic acid, which allowed to dehalogenate efficiently both bromomalonate esters and phenacyl bromide; on the other hand, chloromalonate esters were almost unreactive under the same reaction conditions. Electrochemical and control experiments enabled to elucidate the reaction mechanism, demonstrating the key role of electrons as charge carriers in the observed photocatalytic process.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
