Entwicklung poröser Materialien zur Adsorption von Glyphosat und AMPA sowie Entwicklung eines fotoschaltbaren Bis(cyclopeptids)

  • In the first part of this thesis, the synthesis of several molecularly imprinted polymers (MIPs) and non imprinted polymers (NIPs) and the characterization of their ability to bind glyphosate and AMPA in the aqueous enviroment is described. These polymers are to be used as concentrators in a mobile water monitoring system, and were developed in the framework of the EU-funded Interreg V project „WaterPollutionSensor“. They were produced using block copolymerization of different functional monomers and crosslinkers in various ratios. Phenylphosphonic acid was used as template. For comparison, homopolymers containing only the crosslinkers were also synthesized and all polymers were referend against the commerically available MIP Affinimip® from Affinisep. The composition of the polymers was determined using elemental analysis. Brunauer–Emmett–Teller (BET) and scanning electron microscope (SEM) measurements were carried out to characterize the polymer morphology. The most polymers showed a specific surface between 100 – 400 m2g-1, which is typical for MIPs. The adsorption and elution behavior of the polymers was investigated using NMR and UV/Vis in modified batch and flow experiments. While the polymers based on DMAPMA showed very good adsorption for glyphosate and AMPA, the polymers based on ATH were suitable for both adsorption and elution. The polymers based on EGDMA and ATH showed an imprinting effect while the crosslinker TAHT formed attractive interactions with glyphosate and AMPA and therefore no imprinting effect was observed. The results obtained provided insight into structural parameters that influenced the adsorption properties. In the secound project of this thesis, two bis(cyclopeptides) (BCP) isomers containing a photo-switchable linker were successfully synthesized and isolated. The successful synthesis of both products was confirmed using NMR, elemental analysis, ESI and MALDI mass spectrometry. In cooperation with the Wezenberg group, the switching and binding properties of the two BCPs were analyzed using NMR, ESI and ITC. These experiments showed that both BCPs bind strongly to sulfate anions in DMSO with a 1:1 stoichiometry for the Z and a 2:2 stoichiometry for the E isomer. The high stability of these both sulfate complexes prevented switching from one complex to the other by light. Switching could be achieved by additionally changing the protonation state of the anion using an acid/base mediated stimulus, since hydrogen sulfate is less strongly bound by both isomers.

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Author:Benedict Wyrwol
Advisor:Stefan Kubik
Document Type:Doctoral Thesis
Cumulative document:No
Language of publication:German
Date of Publication (online):2024/05/03
Year of first Publication:2024
Publishing Institution:Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau
Granting Institution:Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau
Acceptance Date of the Thesis:2024/04/25
Date of the Publication (Server):2024/05/06
Page Number:XII, 214
Faculties / Organisational entities:Kaiserslautern - Fachbereich Chemie
DDC-Cassification:5 Naturwissenschaften und Mathematik / 540 Chemie
Licence (German):Creative Commons 4.0 - Namensnennung, nicht kommerziell (CC BY-NC 4.0)