Facile Preparation of the Water-Soluble Singlet Oxygen Traps Anthracene-9,10-divinylsulfonate (AVS) and Anthracene-9,10-diethylsulfonate (AES) via a Heck Reaction with Vinylsulfonate

An easy 2-step method for the synthesis of the water-soluble singlet oxygen trap AES has been developed. The method is based on a novel Heck reaction with sodium vinylsulfonate followed by vinyl hydrogenation. It is shown that the Heck product AVS is also suitable as a water-soluble and colored singlet oxygen trap that allows singlet oxygen to be detected specifically and simply by visual inspection. The cumulative amount of 1O2 generated into the solution can be determined unambiguously by measuring the concentration of the endoperoxides AVSO2 or AESO2 by HPLC or by 1H NMR.