Anthraquinon-2-ylethyl-1 ',2 '-diol (Aqe-diol) as a new photolabile protecting group for aldehydes and ketones

A new photolabile protecting group for aldehydes and ketones, 2-(1,2-dihydroxyethyl) anthraquinone (Aqe-diol) and four caged compounds have been prepared and their photochemistry investigated. Upon 350 nm light irradiation, the caged compounds 2a-d in CH3CN-H2O solution can efficiently release the carbonyl compounds (conversion rate 60-90%), and their uncaging quantum efficiencies were measured, ranging from 0.03 to 0.09. On the basis of HPLC analysis and quenching experiments, a mechanism of the uncaging reaction was suggested. (c) 2006 Elsevier B.V. All rights reserved.