1,3,5-Triaryl-2-penten-1,5-dione anchored to insoluble supports as heterogeneous chromogenic chemosensor

N-Allyl substituted 1,5-diphenyl-3-(4- N-methylaminophenyl)-2-penten-1,5-dione ( 1a ) has been immobilized on a polystyrene backbone, on the surface of mercaptopropyl-functionalized silica or inside the cavities of zeolite NaY. These solids either in suspension or in films act as chemosensors of Fe...

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Bibliographic Details
Published in:Tetrahedron 2004-09, Vol.60 (37), p.8257-8263
Main Authors: Alvaro, Mercedes, Aprile, Carmela, Corma, Avelino, Fornes, Vicente, Garcia, Hermenegildo, Peris, Encarna
Format: Article
Language:English
Subjects:
Chemosensors
Covalent functionalization
Pyrylium dye
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Summary:N-Allyl substituted 1,5-diphenyl-3-(4- N-methylaminophenyl)-2-penten-1,5-dione ( 1a ) has been immobilized on a polystyrene backbone, on the surface of mercaptopropyl-functionalized silica or inside the cavities of zeolite NaY. These solids either in suspension or in films act as chemosensors of Fe 3+ and other strong Lewis acid metal ions such as Cu 2+ and Pb 2+ in buffered water or ethanol. Brönsted acids in low pH aqueous solutions also produce the response of the sensor. For sensing of Fe 3+, depending on the loading of 1a (typically from 2.5 to 0.5 wt%) the solids can test from 10 −2 to 10 −4 M aqueous solutions. The time response can vary from tens of minutes to below a minute depending on hydrophilic/hydrophobic nature of the support and also on the 1a loading. The solid sensor was reused up to 10 times by regenerating after every use the initial form with NaAcO treatment. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.06.090