TY - JOUR A1 - Wagner, R. A1 - Wan, Wei A1 - Biyikal, Mustafa A1 - Benito-Pena, E. A1 - Moreno-Bondi, M.C. A1 - Lazraq, I. A1 - Rurack, Knut A1 - Sellergren, B. T1 - Synthesis, spectroscopic, and analyte-responsive behavior of a polymerizable naphthalimide-based carboxylate probe and molecularly imprinted polymers prepared thereof JF - The journal of organic chemistry N2 - 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-ʟ-phenylalanine (Z-ʟ-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-ʟ-Phe. Compound 1 could be successfully employed in the synthesis of monolithic and thin-film MIPs against Z-ʟ-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. KW - Aminosäuren KW - Enantioselektivität KW - Fluoreszenz KW - Molekular geprägte polymere KW - Sensorfilme PY - 2013 DO - https://doi.org/10.1021/jo3019522 SN - 0022-3263 SN - 1520-6904 VL - 78 IS - 4 SP - 1377 EP - 1389 PB - American Chemical Society CY - Washington, DC AN - OPUS4-27741 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Wan, Wei A1 - Biyikal, Mustafa A1 - Wagner, R. A1 - Sellergren, B. A1 - Rurack, Knut T1 - Fluorescent sensorymicroparticles that 'light-up' consisting of a silica core and a molecularly imprinted polymer (MIP) shell JF - Angewandte Chemie / International Edition N2 - From darkness came light: Incorporation of urea-based fluorescent dyes in an anion-imprinted thin polymer shell coated onto silica microparticles leads to a unique and highly enantioselective fluorescent 'light-up' response to analytes (see scheme, MIP molecularly imprinted polymer). KW - Core–shell particles KW - Enantioselectivity KW - Fluorescence KW - Molecularly imprinted polymers KW - Sensors PY - 2013 DO - https://doi.org/10.1002/anie.201300322 SN - 1433-7851 SN - 1521-3773 SN - 0570-0833 VL - 52 IS - 27 SP - 7023 EP - 7027 PB - Wiley-VCH CY - Weinheim AN - OPUS4-28740 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - CONF A1 - Wan, Wei A1 - Biyikal, Mustafa A1 - Wagner, R. A1 - Sellergren, B. A1 - Rurack, Knut T1 - Enantioselective fluorescence response of molecularly imprinted polymers (MIPs) toward carbobenzyloxy- (Cbz) protected amino acids T2 - 11. Dresdner Sensor Symposium 2013 (Proceedings) N2 - Integration of a polymerisable fluorescent urea-nitrobenzoxadiazole monomer 1 into a few-nanometre thin molecularly imprinted polymer (MIP) shell coated onto a 300 nm silica core with the tetrabutylammonium salt of N-carbobenzyloxy-L-phenylalanine (Cbz- or Z-ʟ-Phe) as the imprinted template yields core/shell MIP nanoparticles that respond to the designated analyte with a strong fluorescence increase in the visible spectral range. The system shows promising imprinting and enantioselectivity factors of 3.6 and 1.9 when benzylmethylacrylate (BMA) is used as co-monomer and ethylene glycol dimethacrylate (EDMA) as cross-linker. A second, naphthalimide-based fluorescent urea 2 is employed in the preparation of MIP thin-films and monolithic polymers for separation techniques. Spectroscopic and chromatographic studies of the MIPs with the analytes Z-ʟ-Phe, Z-ʟ-glutamic acid (Z-ʟ-Glu) and penicilin G (PenG) revealed the (enantio)selective discrimination behaviour of these materials. T2 - 11. Dresdner Sensor Symposium 2013 CY - Dresden, Germany DA - 09.12.2013 KW - Enantioselectivity KW - Molecular imprinting KW - Fluorescence KW - Core-shell nanoparticles KW - Chromatography PY - 2013 SN - 978-3-9813484-5-3 DO - https://doi.org/10.5162/11dss2013/3.2 SP - 53 EP - 58 CY - Wunstorf AN - OPUS4-29818 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -