Programmable synthesis of organic cages with reduced symmetry
Programmable synthesis of organic cages with reduced symmetry
Integrating symmetry-reducing methods into self-assembly methodology is desirable to efficiently realise the full potential of molecular cages as hosts and catalysts. Although techniques have been explored for metal organic (coordination) cages, rational strategies to develop low symmetry organic cages remain limited. In this article, we describe rules to program the shape and symmetry of organic cage cavities by designing edge pieces that bias the orientation of the amide linkages. We apply the rules to synthesise cages with well-defined cavities, supported by evidence from crystallography, spectroscopy and modelling. Access to low-symmetry, self-assembled organic cages such as those presented, will widen the current bottleneck preventing study of organic enzyme mimics, and provide synthetic tools for novel functional material design.
Andrews, Keith G.
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Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Andrews, Keith G.
8236a586-cd06-4ffa-9ba0-863ba1a2cb47
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Andrews, Keith G., Horton, Peter N. and Coles, Simon J.
(2024)
Programmable synthesis of organic cages with reduced symmetry.
Chemical Science.
(doi:10.1039/D4SC00889H).
Abstract
Integrating symmetry-reducing methods into self-assembly methodology is desirable to efficiently realise the full potential of molecular cages as hosts and catalysts. Although techniques have been explored for metal organic (coordination) cages, rational strategies to develop low symmetry organic cages remain limited. In this article, we describe rules to program the shape and symmetry of organic cage cavities by designing edge pieces that bias the orientation of the amide linkages. We apply the rules to synthesise cages with well-defined cavities, supported by evidence from crystallography, spectroscopy and modelling. Access to low-symmetry, self-assembled organic cages such as those presented, will widen the current bottleneck preventing study of organic enzyme mimics, and provide synthetic tools for novel functional material design.
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Submitted date: 5 February 2024
Accepted/In Press date: 31 March 2024
e-pub ahead of print date: 1 April 2024
Additional Information:
KGA conceived, managed, and executed the project. KGA performed the experiments, computations and analysis. PNH and SJC collected and solved the single crystal X-ray diffraction data. KGA wrote the manuscript, with input from all authors.
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Local EPrints ID: 489220
URI: http://eprints.soton.ac.uk/id/eprint/489220
ISSN: 1478-6524
PURE UUID: 0a008eef-219a-4872-99a6-ebaf5f8aabf6
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Date deposited: 18 Apr 2024 16:33
Last modified: 19 Apr 2024 01:36
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Author:
Keith G. Andrews
Author:
Peter N. Horton
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