F. Amatguerri et al., SENSITIZED PHOTOOXIDATION OF 2,3-DIHYDROXYNAPHTHALENES AND 2,7-DIHYDROXYNAPHTHALENES IN ALKALINE WATER, Journal of photochemistry and photobiology. A, Chemistry, 113(3), 1998, pp. 221-224
The Rose Bengal sensitized photooxidation of 2,3-dihydroxynaphthalene
(2,3-DHN) and 2,7-dihydroxynaphthalene (2,7-DHN) in pH 12 water yields
1,1'-dimeric products, the appearance of which can be explained by th
e coupling of radicals formed by primary electron transfer from the an
ionic form of each starting dihydroxynaphthalene to singlet molecular
oxygen or to the excited sensitizer. The dimer from 2,7-DHN is further
oxidised during the irradiation to 6,7-dihydroxyperylene-1,12-quinone
(DHPQ). In the case of 2,3-DHN, phthalic acid has also been detected.
(C) 1998 Elsevier Science S.A.