KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds
Type
ArticleAuthors
Shi, QinqinZhang, Siyuan
Zhang, Junxiang
Oswald, Victoria F.
Amassian, Aram
Marder, Seth R.
Blakey, Simon B.
KAUST Department
KAUST Solar Center (KSC)Material Science and Engineering Program
Organic Electronics and Photovoltaics Group
Physical Science and Engineering (PSE) Division
Date
2016-03-21Online Publication Date
2016-03-21Print Publication Date
2016-03-30Permanent link to this record
http://hdl.handle.net/10754/621521Metadata
Show full item recordAbstract
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.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.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.Publisher
American Chemical Society (ACS)PubMed ID
26996823Relations
Is Supplemented By:- [Dataset]
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: 10754/624538 - [Dataset]
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: 10754/624539