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Inducing Social Self‐Sorting in Organic Cages To Tune The Shape of The Internal Cavity
Author(s) -
Abet Valentina,
Szczypiński Filip T.,
Little Marc A.,
Santolini Valentina,
Jones Christopher D.,
Evans Robert,
Wilson Craig,
Wu Xiaofeng,
Thorne Michael F.,
Bennison Michael J.,
Cui Peng,
Cooper Andrew I.,
Jelfs Kim E.,
Slater Anna G.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007571
Subject(s) - aldehyde , bent molecular geometry , symmetry (geometry) , imine , chemical physics , chemistry , sorting , molecule , crystallography , heteroatom , computational chemistry , topology (electrical circuits) , materials science , computer science , combinatorics , mathematics , geometry , catalysis , organic chemistry , algorithm , ring (chemistry)
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.