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dc.contributor.authorSutton, Christopher
dc.contributor.authorMarshall, Michael S.
dc.contributor.authorSherrill, C. David
dc.contributor.authorRisko, Chad
dc.contributor.authorBredas, Jean-Luc
dc.date.accessioned2015-06-21T09:30:19Z
dc.date.available2015-06-21T09:30:19Z
dc.date.issued2015-06-15
dc.identifier.citationRubrene: The interplay between intramolecular and intermolecular interactions determines the planarization of its tetracene core in the solid state 2015:150615105527002 Journal of the American Chemical Society
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.pmid26075966
dc.identifier.doi10.1021/jacs.5b04066
dc.identifier.urihttp://hdl.handle.net/10754/558300
dc.description.abstractRubrene is one of the most studied molecular semiconductors; its chemical structure consists of a tetracene backbone with four phenyl rings appended to the two central fused rings. Derivatization of these phenyl rings can lead to two very different solid-state molecular conformations and packings: One in which the tetracene core is planar and there exists substantive overlap among neighboring π-conjugated backbones; and another where the tetracene core is twisted and the overlap of neighboring π-conjugated backbones is completely disrupted. State-of-the-art electronic-structure calculations show for all isolated rubrene derivatives that the twisted conformation is more favorable (by -1.7 to -4.1 kcal mol-1), which is a consequence of energetically unfavorable exchange-repulsion interactions among the phenyl side groups. Calculations based on available crystallographic structures reveal that planar conformations of the tetracene core in the solid state result from intermolecular interactions that can be tuned through well-chosen functionalization of the phenyl side groups, and lead to improved intermolecular electronic couplings. Understanding the interplay of these intramolecular and intermolecular interactions provides insight into how to chemically modify rubrene and similar molecular semiconductors to improve the intrinsic materials electronic properties.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/jacs.5b04066
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jacs.5b04066.
dc.titleRubrene: The interplay between intramolecular and intermolecular interactions determines the planarization of its tetracene core in the solid state
dc.typeArticle
dc.contributor.departmentKAUST Solar Center (KSC)
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.identifier.journalJournal of the American Chemical Society
dc.eprint.versionPost-print
dc.contributor.institutionSchool of Chemistry and Biochemistry and Center for Organic Photonics and Electronics Georgia Institute of Technology Atlanta, Georgia 30332-0400 USA
dc.contributor.institutionDepartment of Chemistry and Center for Applied Energy Research University of Kentucky Lexington, Kentucky 40506-0055 USA
kaust.personBredas, Jean-Luc
refterms.dateFOA2016-06-15T00:00:00Z


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