Abstract
The synthesis and full characterization of a quadruple bonded fullerene dimer using self-complementary 2-ureido-4[1H]pyrimidinone units with high dimerization constants is described. The chemical integrity of the monomeric moiety in either compound is fully preserved, also with respect to its redox and UV-Vis behavior. Two novel supramolecular dyads consisting of an oligo(p-phenylene vinylene) (OPV) donor and fullerene (C-60) acceptor are created via quadruple hydrogen bonding upon mixing the fullerene dimer and an OPV dimer. In these supramolecular dyads, singlet-energy transfer from the excited OPV unit to the fullerene causes a strong quenching of the OPV fluorescence. The high association constant of the 2-ureido-4[1H]-pyrimidinone quadruple hydrogen-bonding unit results in high quenching factors (Q(max) greater than or equal to 90). The lower limit obtained for the rate constant for energy transfer (k(EN) greater than or equal to 6 x 10(10) s(-1)) is rationalized in terms of the Forster mechanism.
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