Supramolecular fullerene architectures by quadruple hydrogen bonding

M.T. Rispens, L. Sánchez, E.H.A. Beckers, P.A. Hal, van, A.P.H.J. Schenning, A. El-Ghayoury, E. Peeters, E.W. Meijer, R.A.J. Janssen, J.C. Hummelen

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15 Citations (Scopus)

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 (C60) 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 = 90). The lower limit obtained for the rate constant for energy transfer (kEN = 6 × 1010 s-1) is rationalized in terms of the Förster mechanism.
Original languageEnglish
Pages (from-to)801-803
JournalSynthetic Metals
Volume135-136
DOIs
Publication statusPublished - 2003

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