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

DOI: 10.1002/anie.202007571 DOI Help

Authors: Valentina Abet (University of Liverpool) , Filip T. Szczypiński (Imperial College London) , Marc A. Little (University of Liverpool) , Valentina Santolini (Imperial College London) , Christopher D. Jones (University of Liverpool) , Robert Evans (Aston University) , Craig Wilson (University of Liverpool) , Xiaofeng Wu (University of Liverpool) , Michael F. Thorne (University of Liverpool) , Michael J. Bennison (University of Liverpool) , Peng Cui (University of Liverpool) , Andrew I. Cooper (University of Liverpool) , Kim E. Jelfs (Imperial College London) , Anna G. Slater (University of Liverpool)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Angewandte Chemie International Edition , VOL 365

State: Published (Approved)
Published: July 2020
Diamond Proposal Number(s): 21726

Open Access Open Access

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.

Journal Keywords: cage compounds; molecular materials; multi-component self-assembly; self-sorting; supramolecular chemistry

Subject Areas: Chemistry, Materials


Instruments: I19-Small Molecule Single Crystal Diffraction

Documents:
anie.202007571.pdf