Inducing social self‐sorting in organic cages to tune the shape of the internal cavity

Abstract

Many interesting target guest molecules have low symmetry, yet most methods for synthesising hosts result in highly symmetrical capsules. Methods of generating lower symmetry pores are thus required to maximise the binding affinity in host–guest complexes. Herein, we use mixtures of tetraaldehyde building blocks with cyclohexanediamine to access low-symmetry imine cages. Whether a low-energy cage is isolated can be correctly predicted from the thermodynamic preference observed in computational models. The stability of the observed structures depends on the geometrical match of the aldehyde building blocks. One bent aldehyde stands out as unable to assemble into high-symmetry cages-and the same aldehyde generates low-symmetry socially self-sorted cages when combined with a linear aldehyde. We exploit this finding to synthesise a family of low-symmetry cages containing heteroatoms, illustrating that pores of varying geometries and surface chemistries may be reliably accessed through computational prediction and self-sorting.

Publication DOI: https://doi.org/10.1002/anie.202007571
Divisions: College of Engineering & Physical Sciences > School of Infrastructure and Sustainable Engineering > Chemical Engineering & Applied Chemistry
College of Engineering & Physical Sciences > Aston Institute of Materials Research (AIMR)
Additional Information: © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Funding: EPSRC grants (EP/R005931/1); (EP/L000202, EP/R029431); (EP/N004884/1).
Uncontrolled Keywords: cage compounds,molecular materials,multi-component self-assembly,self-sorting,supramolecular chemistry,Catalysis,Chemistry(all)
Full Text Link:
Related URLs: https://onlinel ... /anie.202007571 (Publisher URL)
http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2020-09-14
Published Online Date: 2020-06-15
Accepted Date: 2020-06-12
Authors: Abet, Valentina
Szczypínski, Filip T
Little, Marc A
Santolini, Valentina
Jones, Christopher D
Evans, Robert (ORCID Profile 0000-0003-1471-201X)
Wilson, Craig
Wu, Xiaofeng
Thorne, Michael F
Bennison, Michael J
Cui, Peng
Cooper, Andrew I
Jelfs, Kim E
Slater, Anna Grace

Download

[img]

Version: Accepted Version

License: Creative Commons Attribution

| Preview

[img]

Version: Published Version

License: Creative Commons Attribution

| Preview

Export / Share Citation


Statistics

Additional statistics for this record