Design of new pincer fullerene ligands thorough [2+3] cycloaddition of the azomethine ylides to fullerene cage: a DFT study

Abstract

ABSTRACTWe have investigated [2+3] cycloaddition reactions occurred thorough the addition of 1,3-dipoles, azomethine ylide derivatives (RHC-NH+-CHR–), to [6, 6] ring fusion bonds of a fullerene C60 cage, in order to design new pincer fullerene ligands. The negative values of [2+3] cycloaddition reaction energies indicate the exothermic character of formation of the considered pincer fullerenes. Exploring of the effects of nature of the flanking arms on fullerene pincer ligands based on the frontier molecular orbital analysis (FMO) indicates that reaction energies well correlate with HOMO of 1,3 dipoles. The pincer-ligated metal complexes obtained by the addition of transition metals to the pincer bites. Natural bonding orbital analyses (NBO) are performed to investigate the delocalisation of the localised bonds and lone pairs of donor nitrogen atoms and the transition metals in the considered pincer-ligated metal complexes. Based on our results, the strongest interaction among all the interactions is due to the delocalisation of electrons from lone pairs of central nitrogen atoms to the LP* of the transition metal, following by the lone pairs of nitrogen atoms in the flanking arms.