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Design, synthesis and computational modelling of aromatic tweezer-molecules as models for chain-folding polymer blends

Greenland, B.W., Burattini, S., Hayes, W. and Colquhoun, H.M. (2008) Design, synthesis and computational modelling of aromatic tweezer-molecules as models for chain-folding polymer blends. Tetrahedron, 64 (36). pp. 8346-8354. ISSN 0040-4020

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To link to this article DOI: 10.1016/j.tet.2008.05.077

Abstract/Summary

Novel 'tweezer-type' complexes that exploit the interactions between pi-electron-rich pyrenyl groups and pi-electron deficient diimide units have been designed and synthesised. The component molecules leading to complex formation were accessed readily from commercially available starting materials through short and efficient syntheses. Analysis of the resulting complexes, using the visible charge-transfer band, revealed association constants that increased sequentially from 130 to 11,000 M-1 as increasing numbers of pi-pi-stacking interactions were introduced into the systems. Computational modelling was used to analyse the structures of these complexes, revealing low-energy chain-folded conformations for both components, which readily allow close, multiple pi-pi-stacking and hydrogen bonding to be achieved. In this paper, we give details of our initial studies of these complexes and outline how their behaviour could provide a basis for designing self-healing polymer blends for use in adaptive coating systems. (C) 2008 Elsevier Ltd. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11285
Uncontrolled Keywords:DONOR-ACCEPTOR INTERACTION, METAL-ION-COMPLEXATION, SUPRAMOLECULAR POLYMERS, SEQUENCE INFORMATION, DUPLEXES DRIVEN, RECOGNITION, CHEMISTRY, MOTIFS, ASSEMBLIES, STABILITY

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