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

Ž. Tomović; 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

doi:10.1021/ja0765417

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

Ž. Tomović, 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 language	English
Pages (from-to)	16190-16196
Journal	Journal of the American Chemical Society
Volume	129
Issue number	51
DOIs	https://doi.org/10.1021/ja0765417
Publication status	Published - 26 Dec 2007

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Tomović, Ž., Van Dongen, J., George, S. J., Xu, H., Pisula, W., Leclère, P. E. L. G., Smulders, M. M. J., Feyter, de, S., Meijer, E. W., & Schenning, A. 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), 16190-16196. https://doi.org/10.1021/ja0765417

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

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.",

author = "{\v Z}. Tomovi{\'c} and {Van Dongen}, J. and S.J. George and H. Xu and W. Pisula and P.E.L.G. Lecl{\`e}re and M.M.J. Smulders and {Feyter, de}, S. and E.W. Meijer and A.P.H.J. Schenning",

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T1 - Star-shaped oligo(p-phenylenevinylene) substituted hexaarylbenzene: Purity, stability, and chiral self-assembly

AU - Tomović, Ž.

AU - Van Dongen, J.

AU - George, S.J.

AU - Xu, H.

AU - Pisula, W.

AU - Leclère, P.E.L.G.

AU - Smulders, M.M.J.

AU - Feyter, de, S.

AU - Meijer, E.W.

AU - Schenning, A.P.H.J.

PY - 2007/12/26

Y1 - 2007/12/26

N2 - 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.

AB - 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.

U2 - 10.1021/ja0765417

DO - 10.1021/ja0765417

M3 - Article

C2 - 18044900

SN - 0002-7863

VL - 129

SP - 16190

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 51

ER -

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

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