Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

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dc.contributor.authorRudebusch, Gabriel
dc.contributor.authorFix, Aaron
dc.contributor.authorHenthorn, Hilary
dc.contributor.authorVonnegut, Chris
dc.contributor.authorZakharov, Lev
dc.contributor.authorHaley, Michael
dc.date.accessioned2014-09-11T21:54:05Z
dc.date.available2014-09-11T21:54:05Z
dc.date.issued2014-06-16
dc.description.abstractWe report the preparation and characterization of a new class of quinoidal thienoacenes. The synthetic route is efficient, high-yielding and scalable with the potential for further functionalization. Single crystal X-ray diffraction reveals that, as size increases, the molecules pack in progressively closer 1D arrangements. The title compounds are shown to have amphoteric redox behaviour by cyclic voltammetry. The anion radicals are studied by EPR spectrometry and by computations. The electron-accepting nature, NIR absorption and the low-lying LUMO energies (ca. −4.0 eV) allude to potential use in materials applications.en_US
dc.description.sponsorshipWe thank the National Science Foundation (CHE-1301485) for support of this research as well as support in the form of instrumentation (CHE-0840478 and CHE-0923589) and computer grants (OCI-0960354). We also thank Dr Brad Rose for guidance on the EPR and computational studies and Prof. Mark Lonergan (University of Oregon) for use of his group's potentiostat. HRMS were obtained at the Mass Spectrometry Facilities and Services Core of the Environmental Health Sciences Center, Oregon State University, supported by grant #P30-ES00210, National Institute of Environmental Health Sciences, National Institutes of Health.en_US
dc.identifierhttp://dx.doi.org/10.1039/C4SC01432D
dc.identifier.citation1. Rudebusch GE, Fix AG, Henthorn HA, Vonnegut CL, Zakharov LN, Haley MM. Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials. Chem Sci. 2014;5(9):3627. doi:10.1039/C4SC01432D.en_US
dc.identifier.issn2041-6539
dc.identifier.urihttps://hdl.handle.net/1794/18239
dc.language.isoen_USen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsCreative Commons BY-NC-SAen_US
dc.subjectQuinoidal thienoacenesen_US
dc.subjectChemical synthesisen_US
dc.subjectOrganic electronicsen_US
dc.titleQuinoidal diindenothienoacenes: synthesis and properties of new functional organic materialsen_US
dc.typeArticleen_US

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