Efficient synthesis of a fluorescent tripod detection system for pesticides by microwave-assisted click chemistry.
A new tripod molecule containing an aromatic core bearing three peracetylated cyclodextrins was synthesized via a microwave-assisted Huisgen 1,3-dipolar cycloaddition and was studied by fluorescence spectroscopy. The photoluminescent properties of complexation phenomena with different pesticides were evaluated in acetonitrile. Fluorescence titrations have been performed to calculate binding constants, sensitivity factors, and limit of detection of the resulting complexes. 2D NMR experiments confirmed the inclusion of pesticide in the hydrophobic cavity of the macrocycle and validated the supramolecular association responsible for the quenching of the fluorescence.
Mallard-Favier
Isabelle
I
Laboratoire de Synthèse Organique et Environnement, E.A. 2599, Université du Littoral Côte d'Opale, 145 Av. M. Schumann, 59140 Dunkerque, France.
Blach
Philippe
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Cazier
Francine
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Delattre
François
F
D000814:Aniline Compounds / Q000737:chemistry; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D015394:Molecular Structure; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D010575:Pesticides / Q000737:chemistry*; D011722:Pyrethrins / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013893:Thiram / Q000737:chemistry
D000814:Aniline Compounds; D003505:Cyclodextrins; D007093:Imidazoles; D000073943:Neonicotinoids; D009574:Nitro Compounds; D009844:Oligosaccharides; D010575:Pesticides; D011722:Pyrethrins; D013893:Thiram; C017160:cypermethrin; C082359:imidacloprid; C030856:pendimethalin