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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Autor: Jiménez Vicent, Diego
Tipo de documento: tese
Data de publicação:2024
País:España
Recursos:Universidad Complutense de Madrid (UCM)
Repositório:Docta Complutense
Idioma:inglês
OAI Identifier:oai:docta.ucm.es:20.500.14352/103244
Acesso em linha:https://hdl.handle.net/20.500.14352/103244
Access Level:Acceso aberto
Palavra-chave:547(043.2)
Química orgánica (Química)
23 Química
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spelling Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic ElectronicsTetrabromo-p-quinodimetanos (TBQs): bloques de construcción versátiles para electrónica orgánicaJiménez Vicent, Diego547(043.2)Química orgánica (Química)23 QuímicaThe 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...Universidad Complutense de MadridMartín León, NazarioSantos Barahona, José ManuelUniversidad Complutense de Madrid20242024-04-1920242024-04-19doctoral thesishttp://purl.org/coar/resource_type/c_db06info:eu-repo/semantics/doctoralThesisapplication/pdfhttps://hdl.handle.net/20.500.14352/103244reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/1032442026-06-02T12:44:21Z
dc.title.none.fl_str_mv Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
Tetrabromo-p-quinodimetanos (TBQs): bloques de construcción versátiles para electrónica orgánica
title Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
spellingShingle Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
Jiménez Vicent, Diego
547(043.2)
Química orgánica (Química)
23 Química
title_short Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
title_full Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
title_fullStr Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
title_full_unstemmed Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
title_sort Tetrabromo-p-quinodimethanes (TBQs): Versatile Building Blocks for Organic Electronics
dc.creator.none.fl_str_mv Jiménez Vicent, Diego
author Jiménez Vicent, Diego
author_facet Jiménez Vicent, Diego
author_role author
dc.contributor.none.fl_str_mv Martín León, Nazario
Santos Barahona, José Manuel
Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547(043.2)
Química orgánica (Química)
23 Química
topic 547(043.2)
Química orgánica (Química)
23 Química
description 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...
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-04-19
2024
2024-04-19
dc.type.none.fl_str_mv doctoral thesis
http://purl.org/coar/resource_type/c_db06
dc.type.openaire.fl_str_mv info:eu-repo/semantics/doctoralThesis
format doctoralThesis
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/103244
url https://hdl.handle.net/20.500.14352/103244
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidad Complutense de Madrid
publisher.none.fl_str_mv Universidad Complutense de Madrid
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,223283

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