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An Investigation of Five Component [3+2] Self-Assembled Cage Formation Using amidinium...carboxylate Hydrogen Bonds

preprint
submitted on 30.04.2021, 06:51 and posted on 03.05.2021, 04:54 by Chriso Thomas, Emer Foyle, Samuel Walker, Nicholas White
The assembly of hydrogen bonded cages using amidinium∙∙∙carboxylate hydrogen bonding interactions was investigated. A new tris-amidinium hydrogen bond donor tecton based on a tetraphenylmethane scaffold was prepared and its self–assembly with the terephthalate anion studied, and a new tricarboxylate hydrogen bond acceptor tecton was synthesized and its assembly with the 1,3-benzenebis(amidinium) hydrogen bond donor explored. In both cases, molecular modelling indicated that the formation of the cages was geometrically feasible and 1H NMR spectroscopic evidence was consistent with interactions between the components in competitive d6- DMSO solvent mixtures. DOSY NMR spectroscopy of both systems indicated that both components diffuse at the same rate as each other, and diffusion coefficients were consistent with cage formation, and with the formation of assemblies significantly larger than the individual components. An X-ray crystal structure showed that one of the assemblies did not have the desired cage structure in the solid state

Funding

Australian Research Council (DE170100200)

History

Email Address of Submitting Author

nicholas.white@anu.edu.au

Institution

Australian National University

Country

Australia

ORCID For Submitting Author

0000-0003-2975-0887

Declaration of Conflict of Interest

No conflict of interest

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