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

Valentina Abet, Filip T Szczypínski, Marc A Little, Valentina Santolini, Christopher D Jones, Robert Evans, Craig Wilson, Xiaofeng Wu, Michael F Thorne, Michael J Bennison, Peng Cui, Andrew I Cooper, Kim E Jelfs, Anna Grace Slater

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)16755-16763
Number of pages9
JournalAngewandte Chemie International Edition in English
Volume59
Issue number38
Early online date15 Jun 2020
DOIs
Publication statusPublished - 14 Sep 2020

Bibliographical note

© 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).

Keywords

  • cage compounds
  • molecular materials
  • multi-component self-assembly
  • self-sorting
  • supramolecular chemistry

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