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 () and a [60]fullerene containing barbituric acid moiety () 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 was greatly quenched by the hydrogen-bonded (Ksv=2.71×104 M−1). A steady and rapid cathodic 0.15 μA cm−2 photocurrent response of the / 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 and . TEM images showed that spherical particles were fabricated by the self-assembly of and through hydrogen-bonding interaction.