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

Autor: Albertus P. H. J. Schenning, Maarten M. J. Smulders, Subi J. George, E. W. Meijer, J.L.J. van Dongen, de S. Feyter, Haolan Xu, Zeljko Tomovic, Philippe Leclère, Wojciech Pisula
Přispěvatelé: Macromolecular and Organic Chemistry, Institute for Complex Molecular Systems
Jazyk: angličtina
Rok vydání: 2007
Předmět:
Zdroj: Journal of the American Chemical Society, 129(51), 16190-16196. American Chemical Society
ISSN: 0002-7863
DOI: 10.1021/ja0765417
Popis: 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 pi-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.
Databáze: OpenAIRE