Star-shaped oligo(p-phenylenevinylene) substituted hexaarylbenzene: Purity, stability, and chiral self-assembly

Z. Tomovic, J. Van Dongen, S.J. George, H. Xu, W. Pisula, P.E.L.G. Leclère, M.M.J. Smulders, S. Feyter, de, E.W. Meijer, A.P.H.J. Schenning

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Abstract

An oligo(p-phenylenevinylene) (OPV)-substituted hexaarylbenzene has been synthesized and fully characterized. Recycling gel permeation chromatography appeared to be a powerful technique to obtain the OPV molecules in a very pure form. X-ray analysis and polarization optical microscopy revealed that the OPV molecule is plastic crystalline at room temperature with an ordered columnar superstructure. In apolar solvents, the molecules self-assemble via a highly cooperative fashion into right-handed chiral superstructures, which are stable even at high temperatures and low concentration. Atomic force microscopy revealed right-handed fibers with a diameter of 6 nm, indicating π-stacked aggregates; on a silicon oxide substrate, supercoiled chiral structures were observed. STM studies on a liquid−solid interface showed that the star-shaped OPV molecule forms an organized monolayer having a chiral hexagonal lattice.
Original languageEnglish
Pages (from-to)16190-16196
JournalJournal of the American Chemical Society
Volume129
Issue number51
DOIs
Publication statusPublished - 26 Dec 2007

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