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Reference type: Journal
Authors: Wagner R, Wan W, Biyikal M, Benito-Peņa E, Moreno-Bondi MC, Lazraq I, Rurack K, Sellergren B
Article Title: Synthesis, Spectroscopic, and Analyte-Responsive Behavior of a Polymerizable Naphthalimide-Based Carboxylate Probe and Molecularly Imprinted Polymers Prepared Thereof.
Publication date: 2013
Journal: Journal of Organic Chemistry
Volume: 78
Issue: (4)
Page numbers: 1377-1389.
DOI: 10.1021/jo3019522
Alternative URL: https://www.researchgate.net/publication/235377893_Synthesis_Spectroscopic_and_Analyte-Responsive_Behavior_of_a_Polymerizable_Naphthalimide-Based_Carboxylate_Probe_and_Molecularly_Imprinted_Polymers_Prepared_Thereof

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
Template and target information: Z-l-phenylalanine, Z-l-Phe, Z-l-glutamic acid, penicillin G

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