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

33 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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CCDC 1436716: Experimental Crystal Structure Determination : 5-fluoro-4-iodo-2,1,3-benzothiadiazole
Shi, Q. (Creator), Zhang, S. (Creator), Zhang, J. (Creator), Oswald, V. F. (Creator), Amassian, A. (Creator), Marder, S. R. (Creator), Blakey, S. B. (Creator), Shi, Q. (Creator), Zhang, S. (Creator), Zhang, J. (Creator), Oswald, V. F. (Creator), Marder, S. R. (Creator) & Blakey, S. B. (Creator), Cambridge Crystallographic Data Centre, May 14 2016
DOI: 10.5517/ccdc.csd.cc1k70ph, http://hdl.handle.net/10754/624538
Dataset
CCDC 1436717: Experimental Crystal Structure Determination : 2-bromo-4,5-diiodo-1,3-thiazole
Shi, Q. (Creator), Zhang, S. (Creator), Zhang, J. (Creator), Oswald, V. F. (Creator), Amassian, A. (Creator), Marder, S. R. (Creator), Blakey, S. B. (Creator), Shi, Q. (Creator), Zhang, S. (Creator), Zhang, J. (Creator), Oswald, V. F. (Creator), Marder, S. R. (Creator) & Blakey, S. B. (Creator), Cambridge Crystallographic Data Centre, May 14 2016
DOI: 10.5517/ccdc.csd.cc1k70qj, http://hdl.handle.net/10754/624539
Dataset

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@article{cce7832cc8f44cf1ac9f79f4f567887b,

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",

}

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.

UR - http://hdl.handle.net/10754/621521

UR - https://pubs.acs.org/doi/10.1021/jacs.5b12259

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 12

ER -

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

Abstract

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

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

Cite this