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

53 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

Bibliographical 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.

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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",

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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

UR - http://www.scopus.com/inward/record.url?scp=84963940241&partnerID=8YFLogxK

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DO - 10.1021/jacs.5b12259

M3 - Article

C2 - 26996823

SN - 0002-7863

VL - 138

SP - 3946

EP - 3949

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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

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

Abstract

Bibliographical note

Access to Document

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Datasets

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