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ChemComm
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Fig. 6 Proposed mechanism for the self-assembly of 1 upon ultrasound
irradiation. The green dotted lines represent aromatic interactions.
The molecular structure of 1 suggests that aromatic interactions
mediate the self-assembly process. The macrocyclic structure was
found to be essential for sonogel formation: three acyclic analogues
all failed to gelate under the same conditions. Molecular modelling,
NMR spectroscopy and X-ray crystallography suggest that 1 is
kinetically trapped in a folded conformation by weak intra-
molecular aromatic interactions. We suggest that when ultra-
sound is applied, the intramolecular interactions are disrupted
allowing self-assembly to take place through intermolecular
aromatic interactions.
This work was funded by Engineering and Physical Sciences
Research Council (EP/J008044/2) and European Research Council 12 Heterocycles and others: (a) K. M. Anderson, G. M. Day, M. J. Paterson,
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(ERC-2012-AdG 320539-duplex). We thank Dr Andrew Bond for
X-ray crystallographic data collection and analysis, Dr Heather
Greer for electron microscopy studies, and Dr Ana M. Belenguer
and Dr Giulio I. Lampronti for PXRD studies.
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Conflicts of interest
There are no conflicts to declare.
Notes and references
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19 Schrodinger Release 2016-4: MacroModel, Schrodinger, LLC, New York,
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