TY - JOUR A1 - Wan, Wei A1 - Biyikal, Mustafa A1 - Wagner, R. A1 - Sellergren, B. A1 - Rurack, Knut T1 - Sensorische Mikropartikel aus einem Silicatkern und einem molekular geprägten Polymer als Schale mit aufleuchtender Fluoreszenz JF - Angewandte Chemie N2 - Und es ward Licht – der Einbau eines auf Harnstoff basierenden Fluoreszenzfarbstoffs in eine mit Anionen geprägte dünne Polymerschale (MIP) auf Silicatmikropartikeln führt zu einem spezifischen und enantioselektiven Aufleuchten der Fluoreszenz in Gegenwart des Zielanalyten. KW - Enantioselektivität KW - Fluoreszenz KW - Kern-Schale-Partikel KW - Molekular geprägte Polymere KW - Sensoren PY - 2013 DO - https://doi.org/10.1002/ange.201300322 SN - 0044-8249 SN - 0932-2140 SN - 1521-3757 VL - 125 IS - 27 SP - 7161 EP - 7165 PB - Wiley-VCH CY - Weinheim AN - OPUS4-28739 LA - deu AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - 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 - Hecht, Mandy A1 - Kraus, Werner A1 - Rurack, Knut T1 - A highly fluorescent pH sensing membrane for the alkaline pH range incorporating a BODIPY dye JF - Analyst N2 - A robust and re-usable dipstick-type fluorescent pH sensor for the alkaline pH range was developed by embedding a brightly fluorescent boron–dipyrromethene (BODIPY) dye bearing an acidic phenol moiety into a polyurethane matrix immobilized on a 3D epoxy-functionalized polymer support. The sensor strip has a dynamic working range of pH 10.0–13.1, i.e., operates in strongly basic media where pH glass electrodes can suffer from alkaline errors, and tolerates a high electrolyte background such as simulated seawater and sewage. This work describes the preparation of the sensing material and provides insight into the features that a hydrogel sensing membrane can bestow on an embedded pH-responsive dye by means of optical spectroscopic investigations. KW - pH-Wert KW - Farbstoffe KW - Fluoreszenz KW - Teststreifen KW - Hydrogel PY - 2013 DO - https://doi.org/10.1039/c2an35860c SN - 0003-2654 SN - 1364-5528 VL - 138 IS - 1 SP - 325 EP - 332 PB - Royal Society of Chemistry CY - Cambridge AN - OPUS4-27638 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Hecht, Mandy A1 - Fischer, Tobias A1 - Dietrich, Paul A1 - Kraus, Werner A1 - Descalzo López, Ana Belén A1 - Unger, Wolfgang A1 - Rurack, Knut T1 - Fluorinated Boron-Dipyrromethene (BODIPY) dyes: bright and versatile probes for surface analysis JF - ChemistryOpen N2 - A family of bright boron-dipyrromethene-type fluorophores with a high number of fluorine atoms (F-BODIPYs) has been developed and characterized by X-ray crystallography and optical spectroscopy. The introduction of 3,5-bis(trifluoromethyl)phenyl and pentafluorophenyl moieties significantly enhances the photostability of such dyes, yielding for instance photostable near-infrared (NIR) fluorophores that show emission maxima>750 nm, when the BODIPY's π system is extended with two (dimethylamino)styryl and (dimethylamino)naphthastyryl moieties, or green-emitting BODIPYs with fluorescence quantum yields of unity. When equipped with a suitable group that selectively reacts for instance with amines, F-BODIPYs can be used as potent dual labels for the quantification of primary amino groups on surfaces by X-ray photoelectron spectroscopy (XPS) and fluorescence, two powerful yet complementary tools for the analysis of organic surface functional groups. The advantage of reactive F-BODIPYs is that they allow a fast and non-destructive mapping of the labelled supports with conventional fluorescence scanners and a subsequent quantification of selected areas of the same sample by the potentially traceable XPS technique. The performance is exemplarily shown here for the assessment of the amino group density on SiO2 supports, one of the most common reactive silica supports, in particular, for standard microarray applications. KW - Amino groups KW - Dyes KW - Fluorescence KW - Surface analysis KW - X-ray photoelectron spectroscopy KW - Amino-Gruppen KW - Farbstoffe KW - Fluoreszenz KW - Oberflächenanalytik KW - Röntgen-Photoelektronen-Spektroskopie PY - 2013 DO - https://doi.org/10.1002/open.201200039 SN - 2191-1363 VL - 2 IS - 1 SP - 25 EP - 38 PB - Wiley-VCH-Verl. CY - Weinheim AN - OPUS4-27783 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Gotor, Raúl A1 - Costero, A. M. A1 - Gil, S. A1 - Parra, M. A1 - Gavina, P. A1 - Rurack, Knut T1 - Boolean operations mediated by an ion-pair receptor of a multi-readout molecular logic gate JF - Chemical communications N2 - A heteroditopic BODIPY dye that performs all basic Boolean operations with a cation (K+) and an anion (F-) as inputs and absorption, transmission and fluorescence as outputs is described. The molecular logic gate can also act as a digital comparator between the inputs. KW - Farbstoffe KW - Molekulare Gatter KW - Ionenpaare KW - Fluoreszenz KW - Boolsche Operationen PY - 2013 DO - https://doi.org/10.1039/c3cc45377d SN - 0022-4936 SN - 1359-7345 VL - 49 IS - 94 SP - 11056 EP - 11058 PB - Royal Society of Chemistry CY - Cambridge AN - OPUS4-29507 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER - TY - JOUR A1 - Climent Terol, Estela A1 - Gröninger, Delia A1 - Hecht, Mandy A1 - Walter, Astrid A1 - Martínez-Mánez, Ramon A1 - Weller, Michael G. A1 - Sancenón, F. A1 - Amorós, P. A1 - Rurack, Knut T1 - Selective, sensitive, and rapid analysis with lateral-flow assays based on antibody-gated dye-delivery systems: The example of triacetone triperoxide JF - Chemistry - A European journal N2 - Set them free: Brightly fluorescent indicators that are loaded into mesoporous silica nanoparticle carriers, capped with bulky antibodies, are released into the lateral flow of a test strip upon analyte arrival. Integration of the system into a rapid, simple flow test with fluorescence readout is applied for the selective and sensitive determination of the presence of triacetone triperoxide (TATP) as a prototype small-molecule analyte (see figure). KW - Farbstoffe KW - Sprengstoffe KW - Fluoreszenz KW - Immunoassays KW - Mesoporöse Materialien PY - 2013 DO - https://doi.org/10.1002/chem.201300031 SN - 0947-6539 SN - 1521-3765 VL - 19 IS - 13 SP - 4117 EP - 4122 PB - Wiley-VCH Verl. CY - Weinheim AN - OPUS4-29508 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -