Photostability enhancement in oligo (phenylene vinylene) systems and their application as heterogeneous photocatalysts

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dc.contributor.advisorSierra Ávila, César Augusto
dc.contributor.authorAcelas Mantilla, Edgar Mauricio de Jesús
dc.contributor.researchgroupGrupo de Investigación en Macromoléculasspa
dc.date.accessioned2022-09-06T13:01:15Z
dc.date.available2022-09-06T13:01:15Z
dc.date.issued2022-08-25
dc.descriptionilustraciones, graficasspa
dc.description.abstractThe first chapter revises the most relevant aspects of phenylene vinylene (PV) systems applied to photocatalysis. Despite the photochemical applications of these conjugated systems that have been widely described and involve photodynamic therapy, pollutants degradation, chemical synthesis, and hydrogen production, among others, it should be noted that a major photostability improvement is required to promote future research in this field. Evidence has pointed out that the vinyl segment directly contributes to the degradation of the PV materials, thus limiting its exploration as organic photocatalysts. Notwithstanding, the scientific literature provides some clues regarding strategies such as structural rigidification and the use of electron-withdrawing groups and inorganic supports to attenuate the PV system fragmentation and therefore enhance the materials’ photocatalytic performance. The second chapter describes the synthesis and chemical/optoelectronic characterization of four target OPVs, prepared via Mizoroki-Heck reaction under solvothermal conditions as a strategy to assemble the conjugated framework with E-E configuration in moderate to high yields. These OPV materials displayed absorption features that included the visible region of the electromagnetic spectrum, suggesting their photochemical activity can be achieved under irradiation with wavelength values >400 nm. Moreover, their optoelectronic properties in both solution and solid-state confirm their potential as organic photocatalysts. Additionally, the preparation of amino OPVs was rationally explored. It was found that the reduction of nitro OPVs employing Na2S/pyridine provides a simple and straightforward synthetic tactic to overcome all the solubility issues related to these materials. The third chapter summarizes the photocatalytic behavior towards the degradation of indigo carmine dye (IC) of the four target OPVs when adsorbed on SiO2 and irradiated using a 350-450 nm LED panel. Different spectroscopic techniques and mass spectrometry allowed us to corroborate that tethering electron-withdrawing groups around the conjugated backbone contribute to the OPV systems’ photostability. OPV 1 resulted in the most efficient and photo-resistant material; its photodegradation products were clearly identified and found to directly relate to the chemical reaction of the conjugated framework with different ROS. The IC photodegradation route was also established, simultaneously identifying the dye degradation products, where the participation of OH· radicals could be disregarded. Nevertheless, reusability experiments confirmed a very low degradation percentage (20%) for the third cycle. The fourth chapter provides detail of the synthetic process and characterization of the chemical immobilization of OPV 1 onto SiO2 and TiO2 along with its copolymerization with rigid and flexible spacers as strategies to improve the photostability of the PV system during the heterogeneous photocatalytic degradation of IC. The assessment of the materials as photocatalyst was simultaneously carried out, where TiO2/OPV 1 displayed outstanding IC degradation performance under visible light. It was found that this process is boosted by the charge transfer process from the OPV moiety towards the TiO2 support, the latter responsible for directly interacting with oxygen to generate ROS producing the dye degradation. Additionally, a direct reductive IC decoloration pathway was observed for this material. On the other hand, when SiO2 was employed as support for OPV 1, the IC degradation was inferior compared to all other materials, even under UVA irradiation. Also, the prepared polymers exhibited a greater photocatalytic activity when 350-450 nm LEDs were used. In summary, both photocatalytic activity and stability significantly improved as demonstrated by TiO2/OPV 1 and the polymer with aromatic rigid spacers Pol-1, which preserved a significantly high IC degradation percentage up to the seventh reuse cycle. This thesis comprises the starting point for future research concerning the rational design of PV-based materials with enhanced properties, performance, and stability for their application as photocatalytic systems. Finally, the fifth chapter discloses the obtained results concerning the treatment of a real textile wastewater sample and 17β-estradiol solutions, the hormone released in the poultry process, using TiO2/OPV 1 (under visible light) and Pol-1 (under UV light) as photocatalysts. This, as a remediation strategy for national environmental issues of concern. In general, it was confirmed that the evaluated PV systems serve as preliminary approaches to address the above-mentioned environmental challenges, comprising a pertinent alternative towards the control of aqueous pollutants.eng
dc.description.abstractEl primer capítulo revisa los aspectos más relevantes del uso de sistemas conjugados tipo fenilen vinileno (FV) en diferentes aplicaciones fotocatalíticas. A pesar de que la actividad fotoquímica de estos sistemas se ha descrito en campos que van desde la terapia fotodinámica en sistemas biológicos, la degradación de contaminantes, la síntesis química y la producción de hidrógeno, es evidente que se requieren mejoras sustanciales en términos de fotoestabilidad que permitan promover futuras investigaciones en este campo, considerando que el fragmento vinílico es el principal responsable de la degradación de estos materiales limitando su exploración como fotocatalizadores. No obstante, existe suficiente evidencia experimental que permite proponer estrategias como el ensamble de estructuras más rígidas, el uso de sustituyentes electroactractores y el uso de soportes inorgánicos para atenuar la fragmentación del sistema FV y, de este modo, mejorar sustancialmente su desempeño en las aplicaciones mencionadas anteriormente. El segundo capítulo describe la síntesis y caracterización química y optoelectrónica de cuatro compuestos oligo (fenilen vinileno) target, preparados a partir de la reacción de Mizoroki-Heck bajo condiciones solvotérmicas como estrategia sintética para el ensamble de la estructura conjugada en configuración E-E con rendimientos de moderados a altos. Se encontró que estos materiales exhiben características de absorción desde la región visible del espectro electromagnético, lo cual sugiere que su actividad fotoquímica puede darse incluso empleando fuentes de irradiación con longitudes de onda >400 nm. Además, sus propiedades optoelectrónicas, tanto en solución como en estado sólido, confirman su potencial como fotocatalizadores orgánicos. Adicionalmente, se exploró la preparación de compuestos amino oligo (fenilen vinileno) a partir de diferentes rutas, encontrándose que la reducción de nitro oligo (fenilen vinilenos) empleando el sistema Na2S/piridina constituye una ruta simple que permite superar los inconvenientes relacionados con la solubilidad de estos materiales. El tercer capítulo muestra el comportamiento fotocatalítico de los cuatro sistemas fenilen vinileno adsorbidos sobre SiO2 frente a la degradación del colorante índigo carmín (IC), empleando como fuente de luz un panel LED de 350-450 nm. Se logró comprobar mediante diferentes técnicas espectroscópicas, así como espectrometría de masas, que los sustituyentes electroatractores contribuyen a la fotoestabilidad de los sistemas. Adicionalmente, fue posible establecer que el sistema OPV 1 es el más eficiente y foto-resistente. Llegando también a identificar claramente sus productos de fotodegradación, los cuales están relacionados principalmente con la reacción del sistema conjugado con diferentes ROS. También, fue posible corroborar la ruta a través de la cual transcurre la degradación del colorante. Simultáneamente se realizó la caracterización de los productos de degradación del índigo carmín, descartándose la participación de radicales OH·. No obstante, experimentos de reusabilidad mostraron una baja capacidad de degradación cercana al 20% para el tercer ciclo. El cuarto capítulo detalla los procesos sintéticos y la caracterización relacionados con el anclaje químico del sistema OPV 1 sobre SiO2 y TiO2 así como su copolimerización con segmentos rígidos y flexibles; estrategias propuestas para la mejora de la estabilidad frente a su uso como fotocatalizadores. Simultáneamente se llevó a cabo su evaluación como fotocatalizadores heterogéneos para la degradación de IC, encontrando que el material TiO2/OPV 1 es capaz de degradar de manera eficiente el IC en tan solo 8 minutos bajo la acción de luz visible. Se determinó que este proceso está facilitado por la transferencia de carga del OPV 1 hacia el TiO2, este último responsable de interactuar con el oxígeno para generar ROS, ocasionando la degradación del colorante. Así mismo, se evidenció reducción directa del IC por el OPV, como ruta de degradación alternativa, exclusiva de este material. Por su parte, cuando se empleó SiO2 como soporte para el OPV 1, la degradación del IC fue baja, inclusive empleando radiación UVA. Por otro lado, los polímeros sintetizados exhibieron una mayor actividad fotocatalítica empleando LEDs de 350-450 nm. En conjunto, la actividad fotocatalítica y la estabilidad mejoraron significativamente, encontrándose que el TiO2/OPV 1 y el polímero con separadores aromáticos rígidos Pol-1, mantienen un elevado porcentaje de degradación del IC hasta el séptimo ciclo de reúso. Lo anterior lleva a que esta tesis se constituya en punto de partida para futuras investigaciones relacionadas con el diseño racional de materiales basados en fenilen vinilenos que puedan presentar mejores propiedades, desempeño y estabilidad para su aplicación como sistemas fotocatalíticos. Finalmente, el quinto capítulo expone los resultados obtenidos en la fotodegradación de colorantes presentes en una muestra real de agua residual textil y de soluciones de 17β-estradiol, hormona excretada en el proceso productivo avícola, empleando como fotocatalizadores los sistemas TiO2/OPV 1 (bajo irradiación con luz visible) y Pol-1 (bajo irradiación con luz UV). Lo anterior como propuesta de remediación a problemáticas de impacto nacional tanto para la industria textil como la industria avícola. En general, se confirma que los sistemas FV evaluados tienen potencial para abordar de manera preliminar estos desafíos ambientales, proyectándose como una alternativa relevante en el control de contaminantes acuosos. (Texto tomado de la fuente)spa
dc.description.degreelevelDoctoradospa
dc.description.degreenameDoctor en Ciencias - Químicaspa
dc.description.researchareaFotocatalizadores orgánicosspa
dc.format.extentxxv, 220 páginasspa
dc.format.mimetypeapplication/pdfspa
dc.identifier.instnameUniversidad Nacional de Colombiaspa
dc.identifier.reponameRepositorio Institucional Universidad Nacional de Colombiaspa
dc.identifier.repourlhttps://repositorio.unal.edu.co/spa
dc.identifier.urihttps://repositorio.unal.edu.co/handle/unal/82253
dc.language.isoengspa
dc.publisherUniversidad Nacional de Colombiaspa
dc.publisher.branchUniversidad Nacional de Colombia - Sede Bogotáspa
dc.publisher.departmentDepartamento de Químicaspa
dc.publisher.facultyFacultad de Cienciasspa
dc.publisher.placeBogotá, Colombiaspa
dc.publisher.programBogotá - Ciencias - Doctorado en Ciencias - Químicaspa
dc.relation.indexedRedColspa
dc.relation.indexedLaReferenciaspa
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dc.subject.ddc540 - Química y ciencias afinesspa
dc.subject.proposaloligo (phenylene vinylene)eng
dc.subject.proposalheterogeneous photocatalysiseng
dc.subject.proposalstabilityeng
dc.subject.proposalchemical immobilizationeng
dc.subject.proposalphotodegradationeng
dc.subject.proposaloligo (fenilen vinileno)spa
dc.subject.proposalfotocatálisis heterogéneaspa
dc.subject.proposalestabilidadspa
dc.subject.proposalanclaje químicospa
dc.subject.proposalfotodegradaciónspa
dc.titlePhotostability enhancement in oligo (phenylene vinylene) systems and their application as heterogeneous photocatalystseng
dc.title.translatedMejora de la fotoestabilidad en sistemas oligo (fenilen vinileno) y sus aplicaciones como fotocatalizadores heterogéneosspa
dc.typeTrabajo de grado - Doctoradospa
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