Novel macrocycles. Part 6. Synthesis, structures and cation binding from optical spectroscopy of 9,10-anthraquinone-crown ethers


Erk C., Erbay E.

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, vol.36, no.2, pp.229-241, 2000 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 36 Issue: 2
  • Publication Date: 2000
  • Doi Number: 10.1023/a:1008072926866
  • Title of Journal : JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • Page Numbers: pp.229-241

Abstract

The 9,10-anthraquinone-[12]crown-4, [15]crown-5 and [18]crown-6 derivatives were synthesized from 1,2-dihydroxy-9,10-anthraquinone and 1,8-dihydroxy-9,10-anthraquinone which were condensed with dihalides or ditosylates of polyethylene glycols in alkali carbonate/DMSO. The 9,10-anthraquinone derived polyoxacyclo-alkanes were characterized with IR, mass spectrometry, H-1, C-13 spectroscopy and elemental analysis. The cation binding properties were studied with UV-vis spectroscopy. The association constants found in acetonitrile were selectively dependent on the cation radius and macrocycle size as well as the molecular structures. The observed results from UV-vis studies, however, showed the stronger complexing role of 1,2-derived macrocycles compared to those of 1,8-derivatives. The theoretical conformational analysis and the energy optimisations of the 9,10-anthraquinone-macrocycles carried out with MM+ method explained the binding results.