Columnar self-assembly in electron-deficient heterotriangulenes

Kivala M, Pisula W, Wang S, Mavrinskiy A, Gisselbrecht JP, Feng X, Muellen K (2013)

Publication Type: Journal article

Publication year: 2013

Journal

Chemistry - A European Journal Wiley

Book Volume: 19

Pages Range: 8117-8128

Journal Issue: 25

DOI: 10.1002/chem.201300253

Abstract

A series of soluble carbonyl-bridged heterotriangulenes, in which flexible n-dodecyl chains are attached through different spacers to the planar nitrogen-centered polycyclic core, have been synthesized. The introduction of triisopropylsilylethynyl moieties enabled, for the first time, the characterization of single-crystal columnar packing of a substituted heterotriangulene by X-ray crystallography. Electrochemical studies disclosed the carbonyl-bridged heterotriangulene core as a reasonably strong acceptor for a reversible two-electron transfer. The tendency of substituted heterotriangulenes to self-assemble in solution, on surfaces, and in the bulk appeared to sensitively depend on the nature of the lateral substituents, their steric demand, and the applied solution processing conditions. It can be concluded that 1) additional phenylene moieties between the heterotriangulene core and the n-dodecyl chains facilitate self-assembly by extending the π-conjugated polycyclic disc, 2) the rod-like ethynylene spacers introduce some additional flexibility and hence lower the overall aggregation tendency, and 3) the combination of both features in the phenylene-ethynylene moieties induces thermotropic liquid crystallinity. Playing the triangle: A series of electron-deficient heterotriangulenes with pendant alkyl chains has been synthesized and their propensity for self-assembly in solution, on a surface, and in the bulk was studied (see figure). A pronounced dependence of the self-assembly behavior on the nature of the spacer between the rigid heterotriangulene core and the flexible alkyl chains was identified. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Involved external institutions

Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE) Université de Strasbourg (UDS) FR France (FR)

How to cite

APA:

Kivala, M., Pisula, W., Wang, S., Mavrinskiy, A., Gisselbrecht, J.-P., Feng, X., & Muellen, K. (2013). Columnar self-assembly in electron-deficient heterotriangulenes. Chemistry - A European Journal, 19(25), 8117-8128. https://doi.org/10.1002/chem.201300253

MLA:

Kivala, Milan, et al. "Columnar self-assembly in electron-deficient heterotriangulenes." Chemistry - A European Journal 19.25 (2013): 8117-8128.

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