We report thiol-on-gold self-assembled monolayers (SAMs) that can be photodeprotected using soft UVirradiation (
= 365 nm) to yield CO
2H functionalized surfaces complementing those reported previously,which yielded NH
2 functionalized surfaces. The photolysis of these SAMs were monitored using a combinationof surface sensitive techniques. In the SAM environment the photodeprotection yields are lower than thoseobtained for equivalent reactions in dilute solution. The protected carboxylic acids SAMs are shown to havea low yield ~50% due to competing photoreduction reactions of the nitro group. The results from infraredstudies show that, as the photolysis progresses, the long chain protected residues reorganize and shield thefunctional COOH groups, thereby reducing the hydrophilic character of the surface.