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Star-Shaped Oligo(p-phenylenevinylene) Substituted Hexaarylbenzene:  Purity, Stability, and Chiral Self-assembly

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posted on 2007-12-26, 00:00 authored by Željko Tomović, Joost van Dongen, Subi J. George, Hong Xu, Wojciech Pisula, Philippe Leclère, Maarten M. J. Smulders, Steven De Feyter, E. W. Meijer, Albertus P. H. J. Schenning
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.

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