Show simple item record

AuthorPotratz, Stefaniedc.contributor.author
Date of accession2016-03-15T06:23:17Zdc.date.accessioned
Available in OPARU since2016-03-15T06:23:17Zdc.date.available
Year of creation2009dc.date.created
AbstractTask of this thesis was nucleophilic substitution at thiophene-halides with O- and N-nucleophiles using copper and palladium catalysts. It was shown that phenols could be coupled under mild reactions conditions using modern copper catalysts. However, reaction conditions were not universal and conversion of diols was not possible. The poisoning of the catalyst due to stable copper-dialcoholate complexes was discussed. For amination of thiophene halides palladium catalysis was most effective. Several reactions conditions according to Buchwald-Hartwig amination were tested. However, reaction conditions compared to literature procedures could not be improved and no N-analogous EDOT was observed. To obtain donor-acceptor-donor co-oligomers and co-polymers, wherein thiophene acts as donor and 1,2,3-triazole as acceptor, azido(oligo-)thiophenes and ethynylated (oligo-)thiophenes were reacted in a copper catalyzed Huisgen-cycloaddition. Due to the instability of 2-azidothiophenes, conjugated thiophene-1,2,3-triazoles had to be synthesized in a three-component one-pot procedure starting from thiophene-halide, sodium azide and terminal alkyne with copper catalyst. Investigation of optoelectronic properties led to the assumption, that the triazole ring rather interrupts the conjugation. Additionally, no intramolecular charge transfer (ICT) could be observed. However, azidomethyl-thiophenes were stable and could be coupled under standard "click"-reaction conditions to terminal alkynes or with TMS-protected alkynes under in situ deprotection conditions. The non-conjugated co-oligomers and co-polymers show properties of the thiophene subunits. With this method it is possible to combimne good properties of polymers (e.g., stability) with those of oligomers (e.g., optoelectronic properties). The application of such co-polymers as semiconductors in organic electronics is conceivable. Through the proper choice of monomers all properties of the resulting co-polymer can be adjusted.dc.description.abstract
Languageendc.language.iso
PublisherUniversität Ulmdc.publisher
LicenseStandard (Fassung vom 01.10.2008)dc.rights
Link to license texthttps://oparu.uni-ulm.de/xmlui/license_v2dc.rights.uri
Keyword1,2,3-triazoledc.subject
KeywordBuchwald-Hartwig-Reaktiondc.subject
KeywordClick reationdc.subject
KeywordHuisgen-cycloadditiondc.subject
Dewey Decimal GroupDDC 540 / Chemistry & allied sciencesdc.subject.ddc
LCSHCatalysisdc.subject.lcsh
LCSHCopperdc.subject.lcsh
TitleTransition metal-catalyzed nucleophilic substitution at thiophene-halidesdc.title
Resource typeDissertationdc.type
DOIhttp://dx.doi.org/10.18725/OPARU-1809dc.identifier.doi
PPN611610027dc.identifier.ppn
URNhttp://nbn-resolving.de/urn:nbn:de:bsz:289-vts-70117dc.identifier.urn
GNDPalladiumdc.subject.gnd
GNDThiophendc.subject.gnd
GNDUllmann, Fritzdc.subject.gnd
FacultyFakultät für Naturwissenschaftenuulm.affiliationGeneral
Date of activation2009-10-08T13:56:00Zuulm.freischaltungVTS
Peer reviewneinuulm.peerReview
Shelfmark print versionZ: J-H 13.425; W: W-H 11.850uulm.shelfmark
DCMI TypeTextuulm.typeDCMI
VTS-ID7011uulm.vtsID
CategoryPublikationenuulm.category
University Bibliographyjauulm.unibibliographie


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record