Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes

William H Gardiner; Matthew Camilleri; Luis A Martinez-Lozano; Sean P Bew; G Richard Stephenson

doi:10.1002/chem.201804755

Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes

Chemistry. 2018 Dec 17;24(71):19089-19097. doi: 10.1002/chem.201804755. Epub 2018 Nov 26.

Authors

William H Gardiner¹, Matthew Camilleri^{1

2}, Luis A Martinez-Lozano¹, Sean P Bew¹, G Richard Stephenson¹

Affiliations

¹ School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK.
² School of Chemistry, University of Bath, Bath, BA2 7AY, UK.

PMID: 30325070
DOI: 10.1002/chem.201804755

Abstract

Covalently linked multiple calixarenes are valued in supramolecular chemistry. This work reports an easy and versatile synthetic route to covalently linked double and triple calix[4]arene and calix[6]arenes by a novel DMF-controlled selective alkylation of a convenient and readily available upper-rim dimethylaminomethyl-substituted tetrahydroxy and hexahydroxy calix[4]arene and -[6]arenes. Synthetic routes to upper-rim functionalised redox active disulfide-linked double-, tetra- and peptidohybrid-calixarenes employing either redox chemistry (CH₂ SH) or thiolates (CH₂ S^- ) are also opened up from the same key starting material.

Keywords: amino acids; calixarenes; multi-calixarenes; peptidocalixarene; selective alkylation; supramolecular chemistry.

Abstract

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