A borazaaromatic analogue of isophthalic acid

PR Ashton, KDM Harris, BM Kariuki, Douglas Philp, JMA Robinson, N Spencer

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A diboradiazaaromatic-2.7-di-tert-butyl-5.9-dihydroxy-5,9-dibora-4,10-diazapyrene-4,10-diium-5,9-diuide-which is a structural analogue of isophthalic acid has been designed and synthesised. This compound is capable of spontaneous dehydration in solution to form linear oligoarthydrides. These oligoanhydrides can be readily hydrolysed to the starting diboradiazaaromatic under appropriate conditions. This unusual reactivity is mirrored in the solid-state behaviour of 2.7-di-tert-butyl-5,9-dihydroxy-5,9-dibora-4.10-diazapyrene-4,10-diium-5,9-diuide. A complex network of hydrogen bonds present in the solid-state structure of the borazaaromatic serve to facilitate a facile solid-state dehydration reaction. once again forming oligoanhydrides of molecular weight greater than 3000 Da.

Original languageEnglish
Pages (from-to)2166-2173
Number of pages8
JournalJournal of Chemical Society, Perkin Transactions 2
Issue number11
DOIs
Publication statusPublished - Nov 2001

Keywords

  • PERFLUOROPHENYL STACKING INTERACTIONS
  • CROSS-COUPLING REACTIONS
  • SOLID-STATE
  • CINCHONA ALKALOIDS
  • ORGANIC-CRYSTALS
  • 10-HYDROXY-10,9-BORAZAROPHENANTHRENE
  • PHOTODIMERIZATION
  • MACROCYCLES
  • REACTIVITY
  • STRATEGY

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