Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore.
Org Biomol Chem
; 7(17): 3499-504, 2009 Sep 07.
Article
in En
| MEDLINE
| ID: mdl-19675906
ABSTRACT
The anion chemosensor 1 based on a urea-activated phthalimide with a stereogenic centre was synthesized using an efficient procedure involving a Curtius rearrangement. Its photophysical properties were estimated in several solvents. Sensor 1 detected fluoride with absorption as well as fluorescence changes and was only observable for this case and not for other halides. The appearance of a new CT complex emission at a longer wavelength and no changes in the singlet lifetime of 1 in the presence of fluoride supported a fluorescence static quenching mechanism. 1H-NMR studies, together with theoretical calculations based on DFT methods at the B3lYP/6-31G* level of theory confirmed the formation of a [1-F]- complex through H-bonding interactions rather than receptor deprotonation in the recognition process. Reversibility of this process was observed upon addition of a protic solvent.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Phthalimides
/
Fluorides
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2009
Document type:
Article
Affiliation country:
Germany
Publication country:
ENGLAND
/
ESCOCIA
/
GB
/
GREAT BRITAIN
/
INGLATERRA
/
REINO UNIDO
/
SCOTLAND
/
UK
/
UNITED KINGDOM