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

Research output: Contribution to journalArticle

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 (CH2SH) or thiolates (CH2S) are also opened up from the same key starting material.

Original languageEnglish
Pages (from-to)19089-19097
Number of pages9
JournalChemistry - A European Journal
Volume24
Issue number71
Early online date26 Nov 2018
DOIs
Publication statusPublished - 17 Dec 2018

Keywords

  • amino acids
  • calixarenes
  • multi-calixarenes
  • peptidocalixarene
  • selective alkylation
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Gardiner, W. H., Camilleri, M., Martinez-Lozano, L. A., Bew, S. P., & Stephenson, G. R. (2018). Upper-Rim Monofunctionalisation in the Synthesis of Triazole- and Disulfide-Linked Multicalix[4]- and -[6]arenes. Chemistry - A European Journal, 24(71), 19089-19097. https://doi.org/10.1002/chem.201804755