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

Handle URI:
http://hdl.handle.net/10754/621521
Title:
KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds
Authors:
Shi, Qinqin; Zhang, Siyuan; Zhang, Junxiang; Oswald, Victoria F.; Amassian, Aram ( 0000-0002-5734-1194 ) ; Marder, Seth R.; Blakey, Simon B.
Abstract:
An 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.
KAUST Department:
Physical Sciences and Engineering (PSE) Division
Citation:
Shi 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.
Publisher:
American Chemical Society (ACS)
Journal:
Journal of the American Chemical Society
Issue Date:
21-Mar-2016
DOI:
10.1021/jacs.5b12259
Type:
Article
ISSN:
0002-7863; 1520-5126
Sponsors:
This 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.
Is Supplemented By:
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:10.5517/ccdc.csd.cc1k70ph; HANDLE:http://hdl.handle.net/10754/624538; 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:10.5517/ccdc.csd.cc1k70qj; HANDLE:http://hdl.handle.net/10754/624539
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorShi, Qinqinen
dc.contributor.authorZhang, Siyuanen
dc.contributor.authorZhang, Junxiangen
dc.contributor.authorOswald, Victoria F.en
dc.contributor.authorAmassian, Aramen
dc.contributor.authorMarder, Seth R.en
dc.contributor.authorBlakey, Simon B.en
dc.date.accessioned2016-11-03T08:31:19Z-
dc.date.available2016-11-03T08:31:19Z-
dc.date.issued2016-03-21en
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.en
dc.identifier.issn0002-7863en
dc.identifier.issn1520-5126en
dc.identifier.doi10.1021/jacs.5b12259en
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.en
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.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleKO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compoundsen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalJournal of the American Chemical Societyen
dc.contributor.institutionDepartment of Chemistry, Emory University, Atlanta, GA, United Statesen
dc.contributor.institutionSchool of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, GA, United Statesen
dc.contributor.institutionDepartment of Chemistry, University of California-Irvine, Irvine, CA, United Statesen
kaust.authorAmassian, Aramen
dc.relation.isSupplementedByShi, 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.cc1k70phen
dc.relation.isSupplementedByDOI:10.5517/ccdc.csd.cc1k70phen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624538en
dc.relation.isSupplementedByShi, 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.cc1k70qjen
dc.relation.isSupplementedByDOI:10.5517/ccdc.csd.cc1k70qjen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624539en
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