Journal article

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

Rhys B Murphy, Pham Duc-Truc, Jonathan M White, Stephen F Lincoln, Martin R Johnston

ORGANIC & BIOMOLECULAR CHEMISTRY | ROYAL SOC CHEMISTRY | Published : 2018

Abstract

The effect of the degree of conformational rigidity and/or flexibility on preorganisation in artificial molecular receptors continues to be actively explored by supramolecular chemists. This work describes a bis-porphyrin architecture, linked via a rigid polycyclic backbone, in which a sterically bulky 2,3,5,6-tetramethylphenyl diimide core restricts rotation to afford two non-interconvertible tweezer conformations; syn- and anti-. After separation, the host-guest chemistry of each conformation was studied independently. The difference in host geometry allows only the syn-conformation to form a strong 1 : 1 bis-porphyrin complex with the diamino ligand 1,4-diazabicyclo[2.2.2]octane (DABCO) (..

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University of Melbourne Researchers

Grants

Funding Acknowledgements

R. B. M wishes to thank Flinders University for the provision of an Australian Postgraduate Award and the Playford Memorial Trust for a PhD top-up scholarship. R. B. M also thanks the following for their efforts and expertise in accurate mass spectrometry: Dr Sally Duck (Monash University) porphyrin compound 9, Dr Craig Brinkworth (Defence Science and Technology Group, Australia) porphyrin compounds syn-3a and anti-3b, Dr Daniel Jardine (Flinders Analytical) all other compounds.