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

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. (2007) Star-Shaped Oligo(p-phenylenevinylene) Substituted Hexaarylbenzene: Purity, Stability, and Chiral Self-assembly† Journal of the American Chemical Society, 129 (51). pp. 16190-16196. ISSN 0002-7863

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Official URL: http://doi.org/10.1021/ja0765417

Related URL: http://dx.doi.org/10.1021/ja0765417

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117795
Deposited On:04 May 2021 04:01
Last Modified:04 May 2021 04:01

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