There have been several demonstrated BODIPY based photocages capable of releasing cargo upon irradiation. Of particular importance to our synthetic design were amine compatible photocages. In this case the amine is connected to the BODIPY cage through a cleavable carbamate linker, which upon irradiation generates an intermediate contact ion pair between the carbocation of the cage and the carbamate anion. Once a solvated ion pair is generated, the intermediate carbocation hydrolyzes to generate the BODIPY alcohol and the carbamate anion relatively slowly hydrolyzes to the amine , releasing carbon dioxide (Scheme 3). The quantum yield of the release of leaving groups by WinterRed and WinterGreen have been previously determined by ferrioxalate actinometry to be 0.11% and 5.5%, respectively . Given the order of magnitude difference in quantum yield, it was important for us to determine the rates of uncaging for both compounds. Fluorescence spectra of each compound in acetonitrile revealed a WinterGreen-WAY excitation maxima of 517 nm and emission maxima at 530 nm. WinterRed-NDMC was far-red shifted with an excitation of 687 nm and emission maxima at 745 nm. These results encouraged us to use a fiber optic Hg-arc lamp as a broad spectrum visible light source for photolysis reactions. The progress of each reaction was monitored by HPLC, where we detected the disappearance of photocage-pharmacophore conjugate with increasing irradiation time.