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

journal contribution
posted on 2023-06-09, 12:57 authored by Barnaby GreenlandBarnaby Greenland, Stefano Burattini, Wayne Hayes, Howard M Colquhoun
Novel ‘tweezer-type’ complexes that exploit the interactions between p-electron-rich pyrenyl groups and p-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 p–p-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 p–p-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.

History

Publication status

  • Published

File Version

  • Published version

Journal

Tetrahedron

ISSN

0040-4020

Publisher

Elsevier

Issue

63

Volume

34

Page range

8346-8354

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2018-04-20

First Compliant Deposit (FCD) Date

2018-04-20

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