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Inducing Social Self-Sorting in Organic Cages to Tune the Shape of the Internal Cavity

submitted on 23.05.2020, 12:31 and posted on 26.05.2020, 08:29 by Valentina Abet, Filip Szczypiński, Marc Little, Valentina Santolini, Christopher D. Jones, Robert Evans, Craig Wilson, Xiaofeng Wu, Michael Thorne, Michael J. Bennison, Peng Cui, Andrew I. Cooper, Kim Jelfs, Anna Slater

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. Here, we use mixtures of tetraaldehyde building blocks 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.







Leverhulme Trust Research Project Grant

Royal Society-EPSRC Dorothy Hodgkin Fellowship

Royal Society University Research Fellowship


Email Address of Submitting Author


University of Liverpool


United Kingdom

ORCID For Submitting Author


Declaration of Conflict of Interest

There are no conflicts to declare.