<div class="csl-bib-body">
<div class="csl-entry">Holzer, B. (2015). <i>Pentacene- and chalcogeneophene-based conjugated compounds as functinonal organic materials</i> [Dissertation, Technische Universität Wien]. reposiTUm. https://doi.org/10.34726/hss.2015.22826</div>
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dc.identifier.uri
https://doi.org/10.34726/hss.2015.22826
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/9131
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dc.description
Zusammenfassung in deutscher Sprache
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dc.description
Abweichender Titel laut Übersetzung der Verfasserin/des Verfassers
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dc.description.abstract
Conjugated pi-electron systems have attracted much attention due to their potential application in advanced electronic materials such as light-emitting diodes (OLEDs), organic field effect transistors (OFETs), and organic photovoltaics (OPV) but also as functional organic compounds capable of two-photon absorption and applicable as nonlinear optics chromophores. The unique electronic properties of organic materials are strongly associated with their pi-electron topology. Alteration of the molecular design of conjugated organic compounds and their functional groups crucially influences electrochemical and photophysical properties (like HOMO/LUMO levels, band gap, quantum yields etc.). Pentacene proved to be a benchmark p-type organic semiconductor, however, its sensitivity to ambient conditions and its low solubility hampers its application in commercial devices. Also, thiophene-based compounds have attracted much attention as advanced electronic materials. Their selenium analogues, selenophene based conjugated pi-electron systems, feature promising materials due to the more electron donating and polarizable selenium. Moreover, selenophenes form more interactive molecular assemblies than their thiophene counterparts. These facts indicate that well-functionalized selenophenes could be utilized as attractive functional materials. However, selenophene-based materials have been little investigated, mainly because of their limited synthetic accessibility. The main goals of the thesis are on the one hand to improve the molecular oxidation stability and solubility of pentacene derivatives by the application of suitable substitutes (e.g. triazoles, isoxazoles and thiophenes) introduced by Copper-catalyzed Azide-Alkyne Huisgen Cycloaddition (CuAAC) or substitution of pentacene-6,13-dione and subsequent reductive aromatization. On the other hand reliable synthetic strategies towards conjugated pi-electron scaffolds based on heteroaromatic moieties (such as triazoles, thiophenes and selenophenes) are presented aiming for improved molecular properties like improved molecular stability, high charge carrier mobility, and enhanced two-photon absorption cross-section. In this context cross-coupling reaction, ring-annulation as well as ring-fragmentation of chalcogenophenes yielding highly conjugated scaffolds are conducted. Moreover, the obtained target compounds are evaluated toward their applicability as functional organic materials.
en
dc.language
English
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dc.language.iso
en
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dc.rights.uri
http://rightsstatements.org/vocab/InC/1.0/
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dc.subject
Organische Feldeffekttransistoren
de
dc.subject
Selenophen
de
dc.subject
Nichtlineare Optik
de
dc.subject
Pentacen
de
dc.subject
Organic Field-Effect Transistors
en
dc.subject
Selenophene
en
dc.subject
Nonlinear Optics
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dc.subject
Pentacene
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dc.title
Pentacene- and chalcogeneophene-based conjugated compounds as functinonal organic materials
en
dc.title.alternative
Pentacen- und Chalcogenophen-basierte konjugierte Verbindungen als funktionelle organische Materialien
de
dc.type
Thesis
en
dc.type
Hochschulschrift
de
dc.rights.license
In Copyright
en
dc.rights.license
Urheberrechtsschutz
de
dc.identifier.doi
10.34726/hss.2015.22826
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dc.contributor.affiliation
TU Wien, Österreich
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dc.rights.holder
Brigitte Holzer
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dc.publisher.place
Wien
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tuw.version
vor
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tuw.thesisinformation
Technische Universität Wien
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dc.contributor.assistant
Hametner, Christian
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tuw.publication.orgunit
E163 - Institut für Angewandte Synthesechemie
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dc.type.qualificationlevel
Doctoral
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dc.identifier.libraryid
AC12670558
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dc.description.numberOfPages
240
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dc.identifier.urn
urn:nbn:at:at-ubtuw:1-78663
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dc.thesistype
Dissertation
de
dc.thesistype
Dissertation
en
tuw.author.orcid
0000-0003-4400-9827
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dc.rights.identifier
In Copyright
en
dc.rights.identifier
Urheberrechtsschutz
de
tuw.advisor.staffStatus
staff
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tuw.assistant.staffStatus
staff
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item.fulltext
with Fulltext
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item.cerifentitytype
Publications
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item.mimetype
application/pdf
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item.openairecristype
http://purl.org/coar/resource_type/c_db06
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item.languageiso639-1
en
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item.openaccessfulltext
Open Access
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item.openairetype
doctoral thesis
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item.grantfulltext
open
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crisitem.author.dept
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
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crisitem.author.orcid
0000-0003-4400-9827
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crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie