A series of 8-hydroxyquinoline azo derivatives with diverse conjugated structures were synthesized and studied to chromogenically detect anions. All the dyes allowed selective detection for fluoride anion in CH3CN via instant deprotonation of the compounds, which was affirmed by UV-Vis absorption and 1H NMR spectra. The chromogenically responding ability increases as the substituent changes from phenyl to naphthyl or anthryl. This result is likely to be related to the enhancement of intramolecular charge transfer (ICT) induced by extension of conjugated structure.
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