Theoretical analysis of substituent effects on building blocks of conducting polymers: 3, 4'-substituted bithiophenes

dc.citation.epage769en_US
dc.citation.issueNumber3en_US
dc.citation.spage764en_US
dc.citation.volumeNumber64en_US
dc.contributor.authorSalzner, U.en_US
dc.contributor.authorKızıltepe, T.en_US
dc.date.accessioned2016-02-08T10:41:53Z
dc.date.available2016-02-08T10:41:53Z
dc.date.issued1999en_US
dc.departmentDepartment of Chemistryen_US
dc.description.abstractSubstituents are widely used to modify the properties of conducting polymers. To study substituent effects on energy levels and energy gaps systematically, CH3-, OH-, NH2-, CN-, and CCH-substituted bithiophenes were examined with density functional theory and NBO analysis. Total charges and :r-electron densities were analyzed separately to examine π- and σ-effects. Second-order perturbation theory was used to quantify conjugation in terms of orbital interactions. NBO orbital energies were employed to investigate the effect of alternating donor-acceptor substitution. Substituents in 3- and 4- positions shift HOMO and LUMO levels in parallel and hardly influence HOMO- LUMO gaps. For level shifting the π-donating and π-accepting abilities are most important; electronegativity mainly influences the σ-orbitals and is less crucial in determining energy gaps. Alternating donor-acceptor substitution leads to HOMO and LUMO energies that are average between those of the parent systems and has little effect on energy gaps.en_US
dc.description.provenanceMade available in DSpace on 2016-02-08T10:41:53Z (GMT). No. of bitstreams: 1 bilkent-research-paper.pdf: 70227 bytes, checksum: 26e812c6f5156f83f0e77b261a471b5a (MD5) Previous issue date: 1999en
dc.identifier.doi10.1021/jo9813944en_US
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/11693/25268
dc.language.isoEnglishen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/jo9813944en_US
dc.source.titleJournal of Organic Chemistryen_US
dc.subjectThiophene derivativeen_US
dc.subjectAnalytic methoden_US
dc.subjectDopingen_US
dc.subjectDrug effecten_US
dc.subjectDrug synthesisen_US
dc.subjectHydrophilicityen_US
dc.subjectLuminescenceen_US
dc.subjectOxidation reduction reactionen_US
dc.subjectPolymerizationen_US
dc.subjectSolubilityen_US
dc.titleTheoretical analysis of substituent effects on building blocks of conducting polymers: 3, 4'-substituted bithiophenesen_US
dc.typeArticleen_US

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Theoretical Analysis of Substituent Effects on Building Blocks of Conducting Polymers;  3,4‘-Substituted Bithiophenes.pdf
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