Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 3, Pages 671-682Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06501g
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Funding
- Region Nord-Pas de Calais (France)
- Ministere de la Jeunesse de l'Education Nationale et de la Recherche (MJENR)
- Fonds Europeens de Developpement Regional (FEDER)
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In this work, the interaction of protonated amino acids with a chromene bearing a fused 18-crown-6 ether moiety was studied by UV-vis and NMR spectroscopy. Initial closed forms of the chromene form monotopic 1 : 1 complexes, the ammonium group being localized inside the crown ether cavity. UV-irradiation leads to transformation of the ring-closed species into the ring-opened form. Depending on the amino acid length, either ditopic or monotopic 1 : 1 complexes are formed. Such complexes are stabilized by the additional H-bonding between the carboxylic group of the acid and the carbonyl oxygen atom of the ring-opened form. Cessation of the irradiation results in ring-closure to the chromene with concomitant change of the complexation mode.
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