C. Erk et E. Erbay, Novel macrocycles. Part 6. Synthesis, structures and cation binding from optical spectroscopy of 9,10-anthraquinone-crown ethers, J INCL P MA, 36(2), 2000, pp. 229-241
Citations number
21
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
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 pol
yethylene 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 aceton
itrile were selectively dependent on the cation radius and macrocycle size
as well as the molecular structures. The observed results from UV-vis studi
es, however, showed the stronger complexing role of 1,2-derived macrocycles
compared to those of 1,8-derivatives. The theoretical conformational analy
sis and the energy optimisations of the 9,10-anthraquinone-macrocycles carr
ied out with MM+ method explained the binding results.