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KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds

dc.contributor.authorShi, Qinqin
dc.contributor.authorZhang, Siyuan
dc.contributor.authorZhang, Junxiang
dc.contributor.authorOswald, Victoria F.
dc.contributor.authorAmassian, Aram
dc.contributor.authorMarder, Seth R.
dc.contributor.authorBlakey, Simon B.
dc.date.accessioned2016-11-03T08:31:19Z
dc.date.available2016-11-03T08:31:19Z
dc.date.issued2016-03-21
dc.identifier.citationShi Q, Zhang S, Zhang J, Oswald VF, Amassian A, et al. (2016) KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds . Journal of the American Chemical Society 138: 3946–3949. Available: http://dx.doi.org/10.1021/jacs.5b12259.
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.pmid26996823
dc.identifier.doi10.1021/jacs.5b12259
dc.identifier.urihttp://hdl.handle.net/10754/621521
dc.description.abstractAn efficient iodination reaction of electron-deficient heterocycles is described. The reaction utilizes KOtBu as an initiator and likely proceeds by a radical anion propagation mechanism. This new methodology is particularly effective for functionalization of building blocks for electron transport materials. Its utility is demonstrated with the synthesis of a new perylenediimide-thiazole non-fullerene acceptor capable of delivering a power conversion efficiency of 4.5% in a bulk-heterojunction organic solar cell. © 2016 American Chemical Society.
dc.description.sponsorshipThis research was supported by the National Science Foundation under the Center for Chemical Innovation in Selective C-H Functionalization (CHE-1205646) and the MRSEC Program (DMR-0820382). The authors thank Professor A. S. Borovik for helpful discussions regarding EPR spectroscopy, Dr. Anil Mehta and the Emory University Solid State NMR Research Center for assistance with solid-state NMR spectroscopy, and Dr. John Bacsa and Marika Wieliczko (Emory X-ray Center) for X-ray structural analysis.
dc.publisherAmerican Chemical Society (ACS)
dc.titleKO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds
dc.typeArticle
dc.contributor.departmentKAUST Solar Center (KSC)
dc.contributor.departmentMaterial Science and Engineering Program
dc.contributor.departmentOrganic Electronics and Photovoltaics Group
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalJournal of the American Chemical Society
dc.contributor.institutionDepartment of Chemistry, Emory University, Atlanta, GA, United States
dc.contributor.institutionSchool of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA, United States
dc.contributor.institutionDepartment of Chemistry, University of California-Irvine, Irvine, CA, United States
kaust.personAmassian, Aram
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1k70ph
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1k70qj
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Shi, Q., Zhang, S., Zhang, J., Oswald, V. F., Amassian, A., Marder, S. R., & Blakey, S. B. (2016). CCDC 1436716: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k70ph. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1k70ph">10.5517/ccdc.csd.cc1k70ph</a> HANDLE: <a href="http://hdl.handle.net/10754/624538">10754/624538</a></li><li><i>[Dataset]</i> <br/> Shi, Q., Zhang, S., Zhang, J., Oswald, V. F., Amassian, A., Marder, S. R., & Blakey, S. B. (2016). CCDC 1436717: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k70qj. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1k70qj">10.5517/ccdc.csd.cc1k70qj</a> HANDLE: <a href="http://hdl.handle.net/10754/624539">10754/624539</a></li></ul>
dc.date.published-online2016-03-21
dc.date.published-print2016-03-30


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