Synthesis of Aziridinofullerene-Porphyrin Mediated by Triethyl Phosphite: Physicochemical and Electrochemical Properties

Abstract

Aziridinofullerene-porphyrin (C60-TPP) dyad was synthesized using triethyl phosphite mediated [2+1] cycloaddition reaction. Structural elucidation of the compound was carried out using NMR and FT-IR spectroscopic methods. The synthesized C60-TPP was further characterized using UV-Vis absorption and photoluminescence emission studies. An optical study of the synthesized compound shows absorption maxima at 424 nm, around 516, 550, and 593 nm with small broad absorption peaks at 360 and at 480 nm. Photoluminescence studies of the compound shows emission maxima at around 597, 652 and 717 nm. Electrochemical studies of the compound shows oxidation potentials at 0.30, 0.52, 0.74 V and reduction potentials at−1.69,−2.07 and−2.42 V with respect to internal Fc/Fc+ reference corresponding to porphyrin and fullerene C60 moiety in the compound and the formation of C60-TPP. Furthermore, the absence of obtain XPS peaks corresponding to nitro group in C60-TPP confirms the conversion of nitro group to aziridine group.