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

Qinqin Shi; Siyuan Zhang; Junxiang Zhang; Victoria F. Oswald; Aram Amassian; Seth R. Marder; Simon B. Blakey

doi:10.1021/jacs.5b12259

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

Qinqin Shi, Siyuan Zhang, Junxiang Zhang, Victoria F. Oswald, Aram Amassian, Seth R. Marder, Simon B. Blakey

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

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.

Original language	English (US)
Pages (from-to)	3946-3949
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	12
DOIs	https://doi.org/10.1021/jacs.5b12259
State	Published - Mar 21 2016

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10.1021/jacs.5b12259

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

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. {\textcopyright} 2016 American Chemical Society.",

author = "Qinqin Shi and Siyuan Zhang and Junxiang Zhang and Oswald, {Victoria F.} and Aram Amassian and Marder, {Seth R.} and Blakey, {Simon B.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

year = "2016",

month = mar,

day = "21",

doi = "10.1021/jacs.5b12259",

language = "English (US)",

volume = "138",

pages = "3946--3949",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "12",

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KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds. / Shi, Qinqin; Zhang, Siyuan; Zhang, Junxiang; Oswald, Victoria F.; Amassian, Aram; Marder, Seth R.; Blakey, Simon B.

In: Journal of the American Chemical Society, Vol. 138, No. 12, 21.03.2016, p. 3946-3949.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - KO t Bu-Initiated Aryl C–H Iodination: A Powerful Tool for the Synthesis of High Electron Affinity Compounds

AU - Shi, Qinqin

AU - Zhang, Siyuan

AU - Zhang, Junxiang

AU - Oswald, Victoria F.

AU - Amassian, Aram

AU - Marder, Seth R.

AU - Blakey, Simon B.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2016/3/21

Y1 - 2016/3/21

N2 - 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.

AB - 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.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

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ER -

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

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CCDC 1436717: Experimental Crystal Structure Determination : 2-bromo-4,5-diiodo-1,3-thiazole

CCDC 1436716: Experimental Crystal Structure Determination : 5-fluoro-4-iodo-2,1,3-benzothiadiazole

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

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Datasets

CCDC 1436717: Experimental Crystal Structure Determination : 2-bromo-4,5-diiodo-1,3-thiazole

CCDC 1436716: Experimental Crystal Structure Determination : 5-fluoro-4-iodo-2,1,3-benzothiadiazole

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