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Fluorescence “Turn-on” Sensing of Amines with Anthracene - based bis o-(Carboxamido)trifluoroacetophenones

Submission Date :
3 / 3 / 2009 , 11 : 48 : 11
Abstract Number :
Presenting Type:
Oral Presentation
Presenting Area :
유기화학 - Oral Presentation for Young Organic Chemists
Authors :
Dowook Ryu, Kyo Han Ahn
Department of Chemistry and Center for Electro-Photo Behaviors in Advance Molecular Systems, POSTECH, San 31 Hyoja-dong, Pohang 790-784, Republic of Korea, Korea
Assigned Code :
금26K4구 Assigend Code Guideline
Presenting Time :
금 10시 : 30분
Selective and sensitive determination of amines are of considerable recent interest due to their importance in areas ranging from food quality control, biomarkers for diseased state, monitoring environmental pollution etc. Several methods for measuring amines based on optical, chromatographical, potentiometrical have been developed so far. Among the various other available methods, fluorescence sensing has advantages because of it’s high sensitivity and compatibility for rapid online and real time analyses of clinical, biological and environmental samples. Trifluoroacetphenone derivatives have been reported to interact selectively with amines. The recognition process is based on the reaction of the trifluoroacetyl (TFA) group of the ligand with the amine to form a hemiaminal. Since the TFA group acts as an electron acceptor, the conversion into the hemiaminal alters the optical properties of the ligand. We have demonstrated that introduction of a H-bonding donor such as carboxamide or sulfonamide group at ortho position to the trifluoroacetyl group stabilizes the hemiaminal adducts and thus enhances the association constant toward amines to a useful level. This H-bonding stabilization approach enabled us to introduce novel fluorescent, colorimetric, and electrochemical probes for mono-, and di-amines. Herein, we wish to disclose some of our recent results obtained from the recognition and sensing of amines.