Functionalization of [60]Fullerene through photochemical reaction for fulleropyrrolidine nanovectors synthesis: Experimental and theoretical approaches

Abstract

To develop novel carbon-based nanocarriers, we proposed grafting on the [60]Fullerene (C60) biologically active molecules. In this process, the formed derivatives described another approach to use photo-cycloaddition reactions for developing the third nanovector generation. As a result, the photoexcitation of C60 and azomethine ylide (AZMYtrp), with visible light, was considered as the most promising pathway to synthesize fulleropyrrolidine (FPL). After complexation with sodium cation (Na+), the error masses of FPL mono-, bis- and tris-adducts were remarkably decreased to -85.93 %, -53.99 % and -99.42 %, respectively. The formed FPL-Na+ complexes presented a significant capacity for trapping OH and OOH free radicals. In fact, their antiradical properties increased when Na+ was bonded with FPL-Na+ mono-adduct carbonyl oxygens. Comparing FPL bis-adducts regioisomers, under three different AZMYtrp forms, the neutral and anionic-neutral forms of FPL cis1 isomer were considered as the most reactive bis-nanocarriers with mole fractions of about 61 % and 46 %, respectively, in contrast to FPL-Na+, when the mixture was dominated by the anionic-neutral form of cis2 isomer with 50.34 %.