Synthesis, spectroscopic, and analyte-responsive behavior of a polymerizable naphthalimide-based arboxylate probe and molecularly imprinted polymers prepared thereof

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Synthesis, spectroscopic, and analyte-responsive behavior of a polymerizable naphthalimide-based arboxylate probe and molecularly imprinted polymers prepared thereof

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Publication Article, peer reviewed scientific
Title Synthesis, spectroscopic, and analyte-responsive behavior of a polymerizable naphthalimide-based arboxylate probe and molecularly imprinted polymers prepared thereof
Author(s) Wagner, Ricarda ; Wan, Wei ; Biyakal, Mustafa ; Benito Pena, Elena ; Moreno-Bondi, Maria ; Lazraq, Issam ; Sellergren, Börje ; Rurack, Knut
Date 2013
English abstract
A naphthalimide-based fluorescent indicator monomer 1 for the integration into chromo- and fluorogenic molecularly imprinted polymers (MIPs) was synthesized and characterized. The monomer was equipped with a urea binding site to respond to carboxylate-containing guests with absorption and fluorescence changes, namely a bathochromic shift in absorption and fluorescence quenching. Detailed spectroscopic analyses of the title compound and various models revealed the signaling mechanism. Titration studies employing benzoate and Z-L-phenylalanine (Z-L-Phe) suggest that indicator monomers such as the title compound undergo a mixture of deprotonation and complex formation in the presence of benzoate but yield hydrogen-bonded complexes, which are desirable for the molecular imprinting process, with weakly basic guests like Z-L-Phe. Compound 1 could be successfully employed in the synthesis of monolithic and thin-film MIPs against Z-L-Phe, Z-L-glutamic acid, and penicillin G. Chromatographic assessment of the selectivity features of the monoliths revealed enantioselective discrimination and clear imprinting effects. Immobilized on glass coverslips, the thin-film MIPs of 1 displayed a clear signaling behavior with a pronounced enantioselective fluorescence quenching dependence and a promising discrimination against cross-analytes.
DOI http://dx.doi.org/10.1021/jo3019522 (link to publisher's fulltext)
Publisher American Chemical Society
Host/Issue Journal of Organic Chemistry;4
Volume 78
ISSN 0022-3263
Pages 1377-1389
Language eng (iso)
Subject(s) photoinduced electron-transfer
fluorescent sensors
recognition
derivatives
receptors
anions
ions
acid
Sciences
Research Subject Categories::NATURAL SCIENCES
Handle http://hdl.handle.net/2043/16615 (link to this page)

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