Synthesis and characterization of norbornadiene-quadricyclane systems for energy storage
Photoswitches represent an avenue to overcome current challenges to develop new tools for versatile applications such as energy storage, bio-imagery, catalysis, etc. In the f ield of Molecular Solar Thermal Energy Storage (MOST), research has drawn increasing attention to norbornadiene (NBD) a photo...
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| Tipo de recurso: | tesis de maestría |
| Fecha de publicación: | 2025 |
| País: | España |
| Institución: | Universitat Politècnica de Catalunya (UPC) |
| Repositorio: | UPCommons. Portal del coneixement obert de la UPC |
| Idioma: | inglés |
| OAI Identifier: | oai:upcommons.upc.edu:2117/456439 |
| Acceso en línea: | https://hdl.handle.net/2117/456439 |
| Access Level: | acceso abierto |
| Palabra clave: | Photochemistry Solar energy -- Storage Organic compounds -- Synthesis) Fotoquímica Energia solar -- Emmagatzematge Compostos orgànics -- Síntesi Àrees temàtiques de la UPC::Enginyeria química |
| Sumario: | Photoswitches represent an avenue to overcome current challenges to develop new tools for versatile applications such as energy storage, bio-imagery, catalysis, etc. In the f ield of Molecular Solar Thermal Energy Storage (MOST), research has drawn increasing attention to norbornadiene (NBD) a photoswitch that converts to quadricyclane (QC) under light irradiation exhibiting high energy storage density. Indeed, the high energy density, reversibility, and adaptability of norbornadiene-quadricyclane (NBD-QC) systems make them stand out from other photoswitches. Nevertheless, the unsubstituted NBD suffers from poor solar spectrum match and weak photoisomerization quantum yield. Consequently, various studies were conducted to enhance the key properties for solar energy storage applications. Among these properties, photoconversion, energy storage, heat release, stability, scalable synthesis, solubility, and half-lifetime appeared as essential for solar energy. To enhance these properties, donor/acceptor-norbornadienes (D/A-NBDs) emerged as one of the most efficient classes of photoswitches. In this way the objective of this thesis is to create and improve high-yielding synthetic procedures for bromo-alkyne derivatives, used as D/ANBD precursors. These precursors will subsequently be transformed into bromosubstituted NBD derivatives through a Diels-Alder cycloaddition. The functionalization of these bromo-NBDs systems using palladium-catalyzed cross-coupling reactions were tested through small-scale batch synthesis. The batch and flow methodologies were developed with the long-term objective of large-scale manufacturing accessibility. This work contributes to the larger goal of developing a sustainable and environmentally friendly MOST system material. |
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