Facile, high-yielding synthesis of deepened cavitands: A synthetic and theoretical study

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Abstract

A wide variety of 2-methyl-resorcinol-based deepened cavitands were synthesised from readily available reagents in a fourstep procedure with overall yields of up to 62%. A systematic variation of the rim was carried out by building up a flexible upper aromatic wall on the rigid cavitand platform through CH 2, CH 2O and CH 2OCH 2 spacers. These aromatic walls were further extended by a Suzuki cross-coupling reaction. Full characterisation of the synthesised cavitands was carried out. The solid-state structure of tetrakis(phenoxymethyl)cavitand was determined by X-ray crystallography. Gas-phase theoretical calculations for this molecule predict the presence of weak T-shaped interactions between the upper phenyl rings. The host- guest complex formation ability of two deepened cavitand hosts towards 4-chloro-benzotrifluoride was proved by photoluminescence method.

Original languageEnglish
Pages (from-to)710-719
Number of pages10
JournalSupramolecular Chemistry
Volume23
Issue number10
DOIs
Publication statusPublished - Oct 1 2011

Keywords

  • Cavitands
  • Host-guest systems
  • Supramolecular chemistry
  • π interactions

ASJC Scopus subject areas

  • Chemistry(all)

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