Mono- and Di-Pyrene [60]Fullerene and [70]Fullerene Derivatives as Potential Components for Photovoltaic Devices

In the present work, we report the successful synthesis and characterization of six (two new) fullerene mono- and di-pyrene derivatives based on C₆₀ and C₇₀ fullerenes. The synthesized compounds were characterized by spectral methods (ESI-MS, ¹H-NMR, ¹³C-NMR, UV-Vis, FT-IR, photoluminescence and photocurrent spectroscopy). The energy of HOMO and LUMO levels and the band gaps were determined from cyclic voltammetry and compared with the theoretical values calculated according to the DFT/B3LYP/6-31G(d) and DFT/PBE/6-311G(d,p) approach for fully optimized molecular structures at the DFT/B3LYP/6-31G(d) level. Efficiency of solar cells made of PTB7: C₆₀ and C₇₀ fullerene pyrene derivatives were analyzed based on the determined energy levels of the HOMO and LUMO orbitals of the derivatives as well as the extensive spectral results of fullerene derivatives and their mixtures with PTB7. As a result, we found that the electronic and spectral properties, on which the efficiency of a photovoltaic cell is believed to depend, slightly changes with the number and type of pyrene substituents on the fullerene core. The efficiency of constructed solar cells largely depends on the homogeneity of the photovoltaic layer, which, in turn, is a derivative of the solubility of fullerene derivatives in the solvent used to apply these layers by spincoating.