ABSTRACT
Certain calix[4]arenes that are anionic and appended with a single hydrophobic substituent can self-assemble into homodimers in water. The unusual behaviours of these assemblies in water solutions are largely attributed to them being formed from like-charged building blocks. We report here a new entry into this series – a difunctionalized analog with two hydrophobic arms, a net – 3 charge on each monomer, and an overall U-shaped ‘clip’ topology. We use 1H NMR, 1-D DOSY and ITC to show that the new compound dimerizes in water but remains monomeric in organic solvents. Various cationic ammonium ion guests are able to drive dimer disassembly in favor of 1:1 host-guest complexes. The extent of competition is proportional to overall guest hydrophobicity.
GRAPHICAL ABSTRACT
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Acknowledgement
We thank Chris Barr for assistance with DOSY NMR.
Disclosure statement
No potential conflict of interest was reported by the authors.
Supplementary material
Supplemental data for this article can be accessed here.