Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
The aim of this Thesis is focused on the synthesis, and application of a new family of compounds, namely tetrabromo-p-quinodimethane (TBQ) as molecular building blocks for the so-called organic electronics.The goal of chapter 1 of the present Thesis is devoted to the design and study of new molecule...
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| Formato: | tesis doctoral |
| Fecha de publicación: | 2024 |
| País: | España |
| Recursos: | Universidad Complutense de Madrid (UCM) |
| Repositorio: | Docta Complutense |
| Idioma: | inglés |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/103244 |
| Acesso em linha: | https://hdl.handle.net/20.500.14352/103244 |
| Access Level: | acceso abierto |
| Palavra-chave: | 547(043.2) Química orgánica (Química) 23 Química |
| Resumo: | The aim of this Thesis is focused on the synthesis, and application of a new family of compounds, namely tetrabromo-p-quinodimethane (TBQ) as molecular building blocks for the so-called organic electronics.The goal of chapter 1 of the present Thesis is devoted to the design and study of new molecules based on tetrabromoanthra-p-quinodimethanes (TBAQ), which are obtained by reaction of a quinoid precursor (anthraquinone) with a phosphorous ylide. Different structural and electronic modifications have been introduced in the aromatic skeleton of the TBQs through the presence of electron donor and acceptor groups, as well as with the presence of sulfur as an heteroatom. As a consequence, a relationship between the presence of the electroactive groups in the starting skeleton of the precursor anthraquinone and the solubility, with the optimization of the reaction conditions and reaction yield has been experimentally established. Furthermore, the synthesis and characterization of all the TBQs obtained has been fully discussed along the memory, as well as in some cases, their respective electronic properties. Thus, 5 new TBQs have been synthesized whose central core is based on anthracene (TBQs 1-5), 3 new TBQs containing two thiophene units (TBQs 6-8), three new bianthracene-containing core (TBQs 9-11) and 5 new TBAQ dimers (TBQd 12-16). It is interesting mentioning that the dimers TBQd are obtained as a 1:1 diastereomeric mixture determined by NMR techniques. Actually, these mixtures could be differentiated only when the subunits of TBAQ are located spatially close. These experimental findings have been supported by theoretical calculations carried out by Prof. Enrique Ortí from ICMol... |
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