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Issue 11, 2014
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Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains

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Abstract

This paper describes a series of three-ring phenylene-ethynylenes (PEs) in which specific, non-covalent arene–arene interactions control conformation in the solid-state. As determined by single crystal X-ray structures, edge-face interactions between benzyl ester side chains and conjugated main chains are observed. In contrast, perfluorobenzyl ester side chains interact cofacially with main chains, resulting in ∼60° torsional angles between neighboring aryl rings in crystalline PEs. Absorbance and fluorescence spectra of films of these compounds reflect these conformational effects, with the spectra of perfluorobenzyl-substituted compounds shifting hypsochromically from solution- to solid-state. In a demonstration of how balancing non-covalent interactions can open the way to new responsive materials, a main chain twisted derivative with octyloxy substituents displayed significant piezochromic behavior.

Graphical abstract: Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains

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Publication details

The article was received on 19 May 2014, accepted on 05 Jul 2014 and first published on 29 Jul 2014


Article type: Edge Article
DOI: 10.1039/C4SC01466A
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Chem. Sci., 2014,5, 4184-4188

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    Twisting and piezochromism of phenylene-ethynylenes with aromatic interactions between side chains and main chains

    R. H. Pawle, T. E. Haas, P. Müller and S. W. Thomas III, Chem. Sci., 2014, 5, 4184
    DOI: 10.1039/C4SC01466A

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