Boron-containing organic compounds are reported to have excellent luminescent properties, however, their ability to photosensitize singlet oxygen generation remains unexplored. The synthesis of several Schiff-base based boranils is reported, starting from commercially available salicylaldehydes and anilines. The iodo-functionalized derivatives were observed to aid in the photosensitized generation of singlet oxygen. Poly(methylmethacrylate) films incorporating these molecules were prepared and were demonstrated to be capable of serving as a reusable heterogeneous medium for the photosensitized degradation of organic water pollutants.