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

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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2007-12, Vol.129 (51), p.16190-16196
Hauptverfasser: Tomović, Željko, van Dongen, Joost, George, Subi J, Xu, Hong, Pisula, Wojciech, Leclère, Philippe, Smulders, Maarten M. J, De Feyter, Steven, Meijer, E. W, Schenning, Albertus P. H. J
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container_end_page 16196
container_issue 51
container_start_page 16190
container_title Journal of the American Chemical Society
container_volume 129
creator Tomović, Željko
van Dongen, Joost
George, Subi J
Xu, Hong
Pisula, Wojciech
Leclère, Philippe
Smulders, Maarten M. J
De Feyter, Steven
Meijer, E. W
Schenning, Albertus P. H. J
description 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.
doi_str_mv 10.1021/ja0765417
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title Star-Shaped Oligo(p-phenylenevinylene) Substituted Hexaarylbenzene:  Purity, Stability, and Chiral Self-assembly
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