Photochemical transformation of 1-naphthol in aerated aqueous solution

Abstract

The phototransformation of 1-naphthol in aerated aqueous solution was investigated by means of product studies and laser flash photolysis. The quantum yield as measured at 313 nm was found to be equal to 3.2 × 10−2 in oxygen-saturated medium while being 10-fold lower in deoxygenated solution. The main photoproducts in aerated medium were 1,4-naphthoquinone, 2-hydroxy-1,4-naphthoquinone and 6-hydroxy-1,4-naphthoquinone. Traces of 1,2-naphthoquinone and 5-hydroxy-1,4-naphthoquinones were detected too. Solvated electrons were detected by laser flash photolysis. The quantum yield of monophotonic ionisation was found to be lower than that of 1-naphthol photolysis indicating that other reaction pathways took place. The mechanisms of naphthoquinones and hydroxynaphthoquinones formation are discussed. © 2005 The Royal Society of Chemistry and Owner Societies.