Synthesis and recognition properties of α-D-glucose-based fluorescent crown ethers incorporating an acridine unit

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Abstract

Two new chiral glucopyranoside-based crown ethers incorporating acridine fluorescent signalling units, 15-membered ligand 1 and 21-membered ligand 2 were synthesized. Their complexation properties toward alkali and alkali earth metal ions, and their enantioselectivity towards chiral ammonium salts were studied by absorption and fluorescence spectroscopic experiments. Macrocycle 1 formed 1:1 complexes with all the metal ions selected and the stability constants were low (lg K < 2.3). The cavitysize of 2 allowed only the complexaton of organic ammonium ions. Crown 2 showed chiral discrimination in case of all the four ammonium salts used as model guest compounds; the highest enantioselectivity (K(R)/K(S) ∼3) was observed for the enantiomers of phenylethyl ammonium perchlorate. Ligand 2 forms much more stable complexes with metal ions; the highest stability constant was obtained for the Ca 2+ complex (lg K = 6.15). The coordination of metal ions by ligand 2 was accompanied by marked fluorescence enhancement, whereas the binding of ammonium ions by the same species resulted in significant fluorescence quenching.

Original languageEnglish
Pages (from-to)253-261
Number of pages9
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume80
Issue number3-4
DOIs
Publication statusPublished - Dec 2014

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Keywords

  • Carbohydrate-based crown ethers
  • Chiral crown ethers
  • Complexation
  • Enantiomeric recognition
  • Fluorescence
  • Photoinduced electron transfer (PET)

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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