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dc.contributor.authorZhang, Siyuan
dc.contributor.authorNaab, Benjamin D.
dc.contributor.authorJucov, Evgheni V.
dc.contributor.authorParkin, Sean
dc.contributor.authorEvans, Eric G B
dc.contributor.authorMillhauser, Glenn L.
dc.contributor.authorTimofeeva, Tatiana V.
dc.contributor.authorRisko, Chad
dc.contributor.authorBredas, Jean-Luc
dc.contributor.authorBao, Zhenan
dc.contributor.authorBarlow, Stephen
dc.contributor.authorMarder, Seth R.
dc.date.accessioned2015-08-12T09:29:43Z
dc.date.available2015-08-12T09:29:43Z
dc.date.issued2015-06-18
dc.identifier.citationZhang, S., Naab, B. D., Jucov, E. V., Parkin, S., Evans, E. G. B., Millhauser, G. L., … Marder, S. R. (2015). n-Dopants Based on Dimers of Benzimidazoline Radicals: Structures and Mechanism of Redox Reactions. Chemistry - A European Journal, 21(30), 10878–10885. doi:10.1002/chem.201500611
dc.identifier.issn09476539
dc.identifier.pmid26088609
dc.identifier.doi10.1002/chem.201500611
dc.identifier.urihttp://hdl.handle.net/10754/566137
dc.description.abstractDimers of 2-substituted N,N'-dimethylbenzimidazoline radicals, (2-Y-DMBI)2 (Y=cyclohexyl (Cyc), ferrocenyl (Fc), ruthenocenyl (Rc)), have recently been reported as n-dopants for organic semiconductors. Here their structural and energetic characteristics are reported, along with the mechanisms by which they react with acceptors, A (PCBM, TIPS-pentacene), in solution. X-ray data and DFT calculations both indicate a longer C-C bond for (2-Cyc-DMBI)2 than (2-Fc-DMBI)2, yet DFT and ESR data show that the latter dissociates more readily due to stabilization of the radical by Fc. Depending on the energetics of dimer (D2) dissociation and of D2-to-A electron transfer, D2 reacts with A to form D+ and A- by either of two mechanisms, differing in whether the first step is endergonic dissociation or endergonic electron transfer. However, the D+/0.5D2 redox potentials-the effective reducing strengths of the dimers-vary little within the series (ca. -1.9V vs. FeCp2+/0) (Cp=cyclopentadienyl) due to cancelation of trends in the D+/0 potential and D2 dissociation energy. The implications of these findings for use of these dimers as n-dopants, and for future dopant design, are discussed. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.publisherWiley
dc.relation.urlhttp://europepmc.org/articles/pmc4529998?pdf=render
dc.rightsArchived with thanks to Wiley
dc.rightsThis file is an open access version redistributed from: http://europepmc.org/articles/pmc4529998?pdf=render
dc.subjectDensity functional calculations
dc.subjectDoping
dc.subjectReaction mechanism
dc.subjectRedox chemistry
dc.subjectStructure elucidation
dc.titlen-Dopants Based on Dimers of Benzimidazoline Radicals: Structures and Mechanism of Redox Reactions
dc.typeArticle
dc.contributor.departmentKAUST Solar Center (KSC)
dc.contributor.departmentLaboratory for Computational and Theoretical Chemistry of Advanced Materials
dc.contributor.departmentMaterial Science and Engineering Program
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemistry - A European Journal
dc.rights.embargodate2016-06-18
dc.eprint.versionPost-print
dc.contributor.institutionSchool of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA 30332-0400 (USA)
dc.contributor.institutionDepartments of Chemical Engineering and Chemistry, Stanford University, Stanford, CA 94303 (USA)
dc.contributor.institutionDepartment of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701 (USA)
dc.contributor.institutionDepartment of Chemistry, University of Kentucky, Lexington, KY 40506 (USA)
kaust.personBredas, Jean-Luc
dc.relation.issupplementedbyDOI:10.5517/cc1460zb
dc.relation.issupplementedbyDOI:10.5517/cc14610d
refterms.dateFOA2020-01-26T12:22:47Z
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Zhang, S., Naab, B. D., Jucov, E. V., Parkin, S., Evans, E. G. B., Millhauser, G. L., … Marder, S. R. (2015). CCDC 1048481: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1460zb. DOI: <a href="https://doi.org/10.5517/cc1460zb">10.5517/cc1460zb</a> HANDLE: <a href="http://hdl.handle.net/10754/624402">10754/624402</a></li><li><i>[Dataset]</i> <br/> Zhang, S., Naab, B. D., Jucov, E. V., Parkin, S., Evans, E. G. B., Millhauser, G. L., … Marder, S. R. (2015). CCDC 1048482: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14610d. DOI: <a href="https://doi.org/10.5517/cc14610d">10.5517/cc14610d</a> HANDLE: <a href="http://hdl.handle.net/10754/624403">10754/624403</a></li></ul>
dc.date.published-online2015-06-18
dc.date.published-print2015-07-20


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