Hydrogen-bonded oligo (p-phenylene vinylene) functionalized with perylene bisimde: self-assembly and energy transfer

Jian Zhang, F.J.M. Hoeben, M.J. Pouderoijen, A.P.H.J. Schenning, E.W. Meijer, F.C. Schryver, de, S. Feyter, de

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52 Citations (Scopus)


We describe the synthesis, supramolecular ordering on surfaces and in solution, and photophysical characterization of OPV4UT-PERY, an oligo(p-phenylenevinylene) (OPV) with a covalently attached perylene bisimide moiety. In chloroform, the molecule forms dimers through quadruple hydrogen bonding of the ureido-s-triazine array. This is supported by scanning tunneling microscopy (STM) studies, which reveal dimer formation at the liquid (1,2,4-trichlorobenzene)/solid (graphite) interface. Moreover, contrast reversal in bias-dependent STM imaging provides information on the ordering and different electronic properties of the oligo(p-phenylenevinylene) and perylene bisimide moieties. In dodecane, the molecule self-assembles into H-type aggregates that are still soluble as a result of the hydrophobic shell formed by the dodecyloxy wedges. The donor-acceptor molecule is characterized by efficient energy transfer from the photoexcited OPV to the perylene bisimide. Mixed assemblies with analogous OPVs lacking the perylene bisimide unit have been prepared in dodecane solution and energy transfer to the incorporated perylene bisimides has been studied by fluorescence spectroscopy.
Original languageEnglish
Pages (from-to)9046-9055
JournalChemistry : A European Journal
Issue number35
Publication statusPublished - 2006


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