Inducing Social Self-Sorting in Organic Cages to Tune the Shape of the Internal Cavity
2020
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.
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