Structural Effect of Perylene Derivatives on Their Interaction with Reduced Graphene Oxide Monolayers

Abstract The elucidation of factors influencing energy transfer in hybrid systems based on organic sensitizers and two-dimensional carbon materials is an important problem of thin-film chemistry, whose solution will make it possible to rationalize the design of new type of optoelectronic devices. The role of substituents in a perylene molecule in the energy transfer between a chromophore and a reduced graphene oxide (GO) monolayer was eludicated by Raman spectroscopy. It was shown that the adsorption of a perylene derivative with a planar geometry on reduced GO leads to fluorescence quenching and enhances Raman scattering in the chromophore. At the same time, no Raman bands from perylene can be detected after a “planar” chromophore is immobilized on pure silicon or perylene with isopentyl substituents is immobilized on a reduced GO monolayer despite the presence of perylene fluorescence peaks in the spectra. The surface-enhanced Raman scattering is caused by strong interactions between the unsubstituted chromophore and reduced GO due to aromatic stacking, which interactions provide efficient energy transfer between the components. The interactions between the substituted chromophore and the carbon framework are weak due to steric hindrances, being expressed in the absence of Raman scattering enhancement.