Photocleavage and Photophysical Properties of Amine Releasing BODIPY Derivatives

To date, there is still a lack of suitable methods for chemical modification of graphene surfaces in situ. Photocleavable compounds have great potential for in situ modification of chemical species with visible light, leaving desired chemical functionalities on the surface. Green light-sensitive boron dipyrromethene (BODIPY) derivatives can release diverse cargos, including biologically important amines. In this study, green light-sensitive photocleavable BODIPY derivatives with different aromatic anchors for surface binding were designed and synthesized with the ultimate goal of selective graphene surface patterning. The effects of different aromatic anchor groups on photocleaving capability, their structural and photophysical properties and photocleavage in different conditions were studied. Photocleavage was significantly faster, and more controllable photoreaction was achieved in inert conditions than in the presence of oxygen (ambient air). In addition, pyrene as an anchor lowered fluorescence quantum yield and intensities of absorption and emission maxima of the entire BODIPY derivative, making it a poorer fluorophore than the derivatives with the naphthalene and phenyl anchors.