The present PhD thesis entitled “Design, Synthesis and Evaluation of Chromofluorogenic
Probes for Contaminating Species” is focused on the development of
new chromo-fluorogenic sensors based on the principles of molecular recognition.
The first part of this thesis is focused on the design and synthesis of suitable
organic compounds as sensors for metal cations. The selected sensing paradigm
was the binding site-signalling subunit approach. The synthetized receptors
employs a chromophore (fluorescein or BODIPY) skeleton as signalling subunit and
it is functionalized with aminoethoxy moieties as binging site; the metal
coordination reduces the electron-donating ability of the nitrogen atom
conjugated to the chromophore resulting in optical changes noticeable to the
naked-eye. The sensing behavior is highly selective to trivalent cations (Fe3+, Al3+
and Cr3+) with remarkable limits of detection. The receptors based on BODIPYdyes
retain the sensing abilities in mixed aqueous solutions.
The remaining chapters of the thesis are centered in the detection and removal of
nerve agents surrogates. The design, synthesis, characterization and application of
new BODIPY chemosensors were studied. These chemosensors were designed
containing different reactive sites in order to avoid interferences produced by
acids or hydrolysis products, and also be able to distinguish between the different
G-nerve agent mimics (DCNP and DFP). The BODIPY-probes allows screening of
nerve agent surrogates with remarkable limits of detection and optical changes
noticeable to the naked-eye. The sensing abilities are retained in solid support,
allowing practical application in real-time monitoring by simple colorimetric tests.
The displacement assay approach has been used to develop a selective sensor for
V-nerve agent surrogates versus G-type. For this purpose, two Eu3+ and Au3+
BODIPY-complexes were prepared. In this case, V-surrogate is capable of
coordinate the metallic center, releasing the BODIPY ligand. This causes a change
in the optical properties visible to the naked-eye.
Finally, the use of supramolecular-based organocatalyst for destruction of OP
nerve agent surrogates was studied. Hydrolysis studies were performed in
presence of 1,3-diindolylureas and thioureas, amines, aminoalcohol and glycols.
Addition of catalyst enhances the electrophilic character of the P atom, and the
final nucleophilic attack of water that results in the formation of the
corresponding less toxic organophosphate derivatives, thus higher hydrolysis
rates are obtained. / Barba Bon, A. (2014). Design, Synthesis and Evaluation of Chromo-fluorogenic Probes for Contaminating Species [Tesis doctoral no publicada]. Universitat Politècnica de València. https://doi.org/10.4995/Thesis/10251/48521 / TESIS
| Identifer | oai:union.ndltd.org:upv.es/oai:riunet.upv.es:10251/48521 |
| Date | 31 March 2015 |
| Creators | Barba Bon, Andrea |
| Contributors | Gil Grau, Salvador, Sancenón Galarza, Félix, Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny |
| Publisher | Universitat Politècnica de València |
| Source Sets | Universitat Politècnica de València |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/doctoralThesis, info:eu-repo/semantics/acceptedVersion |
| Rights | http://rightsstatements.org/vocab/InC/1.0/, info:eu-repo/semantics/openAccess |
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