Abstract
Two novel pyrazolino [60] fullerenes 2a – 2b have been prepared by 1, 3 dipolar cycloaddition reaction of nitrile imines, generated in situ from hydrazones 1a – 1b, to C60. All the synthesized compounds were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR and mass spectral analysis. Charge-transfer interactions in the ground state between the indole ring and the fullerene cage has been monitored by photophysical and electrochemical studies. Electrochemical properties of the new dyads 2a-b showed better electron affinity with respect to C60. Steady state absorption and emission spectra studied as a function of dielectric constant of the medium, showed efficient electron transfer from indole to fullerene moiety in polar solvents such as CH2Cl2. Fluorescence lifetimes of the dyads 2a and 2b studied by nanosecond flash photolysis showed faster fluorescence decay of the dyads as compared by reference compound N-Methylpyrrolidino[60]fullerene.
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