Multiple hydrogen-bond-induced supramolecular nanostructure from a pincer-like molecule and a [60]fullerene derivative

A new supramolecular self-assembled system between a perylene bisimide bearing diaminopyridine-substituted isophthalamide groups (PP) and a 60]fullerene containing barbituric acid moiety (C₆₀bar) through a complementary six-point hydrogen-bonding interaction was constructed. The formation of hydrogen bonding was confirmed by ¹H NMR spectra studies in CDCl₃. Fluorescence quenching experiments indicated that the fluorescence of PP was greatly quenched by the hydrogen-bonded C₆₀bar (K_sv=2.71×10⁴ M⁻¹). A steady and rapid cathodic 0.15 μA cm⁻² photocurrent response of the PP/C₆₀bar film deposited onto an ITO electrode was produced under the irradiation of 20 mW cm⁻² white light, indicating the presence of photo-induced electron transfer between PP and C₆₀bar. TEM images showed that spherical particles were fabricated by the self-assembly of PP and C₆₀bar through hydrogen-bonding interaction.