Quinolinotriazole-beta-cyclodextrin and its adamantanecarboxylic acid complex as efficient water-soluble fluorescent Cd(2+) sensors.
A novel beta-cyclodextrin derivative 1 bearing 8-hydroxyquinolino and triazole groups was synthesized in satisfactory yield by 'click chemistry'. With a good water solubility up to 0.03 mol/L, 1 exhibited an effective switch-on fluorescence response to Cd(2+) over other common metal ions under physiological conditions. Studies on the recognition mechanism indicated that the cooperative coordination of Cd(2+) with both the 8-hydroxyquinolino moiety excluded from the beta-CD cavity and the triazole moiety was a crucial and basic factor to achieve the fluorescent sensing process. Significantly, spectrophotometric studies also demonstrated that, after inclusion complexation with 1-adamantanecarboxylic acid sodium salt (AdCA), the resultant 1/AdCA system gave a more effective fluorescent sensing to Cd(2+) through a cyclodextrin/substrate/Cd(2+) triple binding mode.
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, PR China.
Ying-Ming
YM
Zhang
Yong
Y
Chen
Zhi-Qiang
ZQ
Li
Nan
N
Li
Yu
Y
Liu
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011807:Quinolizines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D021241:Spectrometry, Mass, Electrospray Ionization; D047392:beta-Cyclodextrins / Q000737:chemistry*
D005456:Fluorescent Dyes; D011807:Quinolizines; D047392:beta-Cyclodextrins; C012698:adamantanecarboxylic acid; C031215:betadex; D000218:Adamantane