Visualization of various supramolecular assemblies of oligo(para- phenylenevinylene)-melamine and perylene bisimide

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

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Abstract

A melamine derivative has been covalently equipped with two oligo(para-phenylenevinylene) (OPV) chromophores. This procedure yields a bifunctional molecule with two hydrogen-bonding arrays available for complementary binding to perylene bisimide derivatives. Depending on the solvent, hydrogen-bonded trimers, tetramers, and dimers on a graphite surface are observed for pure OPV-melamine by using scanning tunneling microscopy (STM). Upon the addition of perylene bisimide, linear tapes of perylene bisimide, 12-membered rosettes that consist of alternating hydrogenbonded OPV-melamine and perylene bisimide moieties are visualized. These results provide direct evidence for the possible modes of hydrogen bonding within a supramolecular co-assembly in solution. Subsequently, the optical properties of pure OPV-melamine and co-assemblies with a perylene bisimide derivative were characterized in solution. In an apolar solvent, OPV-melamine self-assembles into chiral superstructures. Disassembly into molecularly dissolved species is reversibly controlled by concentration and tempera-ture. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, Ï€-stacked dye assemblies of enhanced stability that are characterized by fluorescence quenching of the constituent chromophores. Titration experiments reveal that a mixture of hydrogen-bonded oligomers is present in solution, rather than a single discrete assembly. The solution experiments are consistent with the STM results, which revealed various supramolecular assemblies. Our system is likely not to be optimally programmed to obtain a discrete co-assembled structure in quantitative yield. -© 2008 Wiley-VCH Verlag GmbH & Co. KGaA
Original languageEnglish
Pages (from-to)8579-8589
JournalChemistry : A European Journal
Volume14
Issue number28
DOIs
Publication statusPublished - 2008

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