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Issue 7, 2002
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Singlet-energy transfer in quadruple hydrogen-bonded oligo(p-phenylenevinylene)–fullerene dyads

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Abstract

Two novel supramolecular dyads consisting of an oligo(p-phenylenevinylene) (OPV) donor and fullerene (C60) acceptor are created via quadruple hydrogen bonding using self-complementary 2-ureido-4[1H]-pyrimidinone units. In the 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 (Qmax ≥ 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. Photoinduced electron transfer does not occur in these hydrogen-bonded dimers, even in polar solvents. The absence of charge separation is ascribed to a low electronic coupling between the donor and acceptor in the excited state as result of the long distance between the chromophores.

Graphical abstract: Singlet-energy transfer in quadruple hydrogen-bonded oligo(p-phenylenevinylene)–fullerene dyads

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Publication details

The article was received on 31 Jan 2002, accepted on 17 Apr 2002 and first published on 09 May 2002


Article type: Paper
DOI: 10.1039/B201186G
Citation: J. Mater. Chem., 2002,12, 2054-2060
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    Singlet-energy transfer in quadruple hydrogen-bonded oligo(p-phenylenevinylene)–fullerene dyads

    E. H. A. Beckers, P. A. van Hal, A. P. H. J. Schenning, A. El-ghayoury, E. Peeters, M. T. Rispens, J. C. Hummelen, E. W. Meijer and R. A. J. Janssen, J. Mater. Chem., 2002, 12, 2054
    DOI: 10.1039/B201186G

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