Solid-state and solution phase reactivity of 10-hydroxy-10,9-boroxophenanthrene: a model building block for self-assembly processes

L M Greig, B M Kariuki, S Habershon, N Spencer, R L Johnston, K D M Harris, Douglas Philp

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

The relative stability of 10-hydroxy-10,9-boroxophenathrene and its electrophilic reactivity are traced through experiment and calculations to the partially aromatic character of the boron-containing heterocyclic ring. The electrophilic reactivity of 10-hydroxy-10,9-boroxophenathrene towards itself in the solid state and towards other nucleophiles in solution is described. The mechanism of the solid-state reaction has been characterised by both X-ray diffraction and thermal analysis. In solution, however, 10-hydroxy-10,9-boroxophenathrene does not react with itself, although it does react rapidly and reversibly with benzylic alcohols in solution, even at low temperatures. This selective and reversible reaction is ideal for use in self-assembly processes.

Original languageEnglish
Pages (from-to)701-710
Number of pages10
JournalNew Journal of Chemistry
Volume26
Issue number6
DOIs
Publication statusPublished - 2002

Keywords

  • POWDER DIFFRACTION DATA
  • CRYSTAL-STRUCTURE DETERMINATION
  • HETEROAROMATIC COMPOUNDS
  • BIOLOGICAL PRINCIPLES
  • MOLECULAR RECOGNITION
  • THERMODYNAMIC CONTROL
  • CINCHONA ALKALOIDS
  • GENETIC ALGORITHM
  • ISOPHTHALIC ACID
  • COVALENT BONDS

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