AbstractsBiology & Animal Science

Imprinted fluorogenic receptors composed of a polymerisable naphthalimide-based oxyanion probe

by Ricarda Wagner

Institution: Technische Universität Dortmund
Year: 2013
Keywords: 540
Record ID: 1099907
Full text PDF: http://hdl.handle.net/2003/30137


The presented work is part of a DFG project. The goal of the project was the design, synthesis and evaluation of molecularly imprinted polymers (MIPs) with optical sensing properties, aimed at the selective detection of anionic guest-molecules. The projects combines the rapidly growing field of anion-detection with molecular imprinting. Upon integration of tailor-made monomers with fluorogenic properties into MIPs, selective materials with the dual ability to bind a specific anionic analyte and simultaneously report the binding by a luminescence change were developed. In order to meet this goal in a first step urea-based monomers containing a chromophoric π-system were designed and synthesised. Their affinity towards anionic guestmolecules and thus their applicability for the integration into MIPs was investigated. Furthermore, it was evaluated, if the binding event is transduced into a spectroscopically detectable signal. Based on the monomers showing the desired properties, MIPs in different formats were developed and investigated. Monolithic bulk polymers were prepared in order to evaluate the separation properties of the polymers. For applications with the focus on sensory characteristics thin-film MIPs on glass-supports were synthesised. The materials prepared for the presented work meet the goal of the project in an outstanding way. Upon chromatographic evaluation, MIPs prepared from the novel monomers showed pronounced discrimination between their template and structurally related analytes. Furthermore, the polymers were able to discriminate enantioselectively. Also the polymers in film-format revealed strong enantioselective discrimination and selectivity towards structurally related analytes. The binding of the template induces pronounced fluorescence quenching. This quenching is not, respectively less pronounced observed for the other enantiomer and other analytes. In summary MIPs based on tailor-made monomers with fluorogenic properties were successfully prepared. These polymers detect their respective template selectively, leading to high imprinting factors in chromatographic evaluations and strong luminescence changes in spectroscopical tests. Ziel der vorliegenden, im Rahmen eines DFG Projektes erstellten Arbeit waren das Design, die Synthese und die Untersuchung molekular geprägter Polymere (MIPs) mit optischen Sensoreigenschaften zur selektiven Detektion anionischer Gastmoleküle. Das Projekt verbindet das wachsende Feld der Anion-Detektion mit dem Bereich der molekularen Prägung. Durch den Einbau speziell entwickelter, funktioneller Monomere mit fluorogenen Eigenschaften in molekular geprägte Polymere wurden selektive Materialien hergestellt, die die Bindung eines spezifischen, anionischen Analyten durch eine einfach zu detektierende Änderung in der Luminiszenz anzeigen. Im Zuge dessen wurden zunächst Harnstoff-basierte, ein chromophores π-System enthaltende, Monomere entwickelt. Um ihre Attraktivität für den Einbau in ein Sensor-MIP zu überprüfen, wurden die Affinität der Monomere zu anionischen…