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  C-H Arylation of Unsubstituted Furan and Thiophene with Acceptor' Bromides: Access to Donor-Acceptor-Donor-Type Building Blocks for Organic Electronics

Matsidik, R., Martin, J., Schmidt, S., Obermayer, J., Lombeck, F., Nuebling, F., et al. (2015). C-H Arylation of Unsubstituted Furan and Thiophene with Acceptor' Bromides: Access to Donor-Acceptor-Donor-Type Building Blocks for Organic Electronics. Journal of Organic Chemistry, 80(2), 980-987. doi:10.1021/jo502432e.

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jo502432e_si_001.pdf (Supplementary material), 2MB
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Matsidik, Rukiya1, Author
Martin, Johannes1, Author
Schmidt, Simon1, Author
Obermayer, Johannes1, Author
Lombeck, Florian1, 2, Author
Nuebling, Fritz1, Author
Komber, Hartrnut3, Author
Fazzi, Daniele4, Author              
Sommer, Michael1, 5, Author
Affiliations:
1Universität Freiburg, Institut für Makromolekulare Chemie, Stefan-Meier-Strasse 31, 79104 Freiburg, Germany, ou_persistent22              
2Optoelectronics Group, Cavendish Laboratory, J J Thomson Avenue, Cambridge CB3 0HE, U.K., ou_persistent22              
3Leibniz Institut für Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, Germany, ou_persistent22              
4Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
5Universität Freiburg, Freiburger Materialforschungszentrum (FMF), Stefan-Meier-Strasse 21, 79104 Freiburg, Germany, ou_persistent22              

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 Abstract: Pd-catalyzed direct arylation (DA) reaction conditions have been established for unsubstituted furan (Fu) and thiophene (Th) with three popular acceptor building blocks to be used in materials for organic electronics, namely 4,7-dibromo-2,1,3-benzothiadiazole (BTBr2), N,N'-dialkylated 2,6-dibromonaphthalene-1,4,5,8-bis(dicarboximide) (NDIBr2), and 1,4-dibromotetrafluorobenzene (F4Br2). Reactions with BTBr2, F2Br4, and NDIBr2 require different solvents to obtain high yields. The use of dimethylacetamide (DMAc) is essential for the successful coupling of BTBr2 and F4Br2, but detrimental for NDIBr2, as the electron-deficient NDI core is prone to nucleophilic core substitution in DMAc as solvent but not in toluene. NDIFu2 is much more planar compared to NDITh4, resulting in an enhanced charge-transfer character, which makes it an interesting building block for conjugated systems designed for organic electronics. This study highlights direct arylation as a simple and inexpensive method to construct a series of important donor-acceptor-donor building blocks to be further used for the preparation of a variety of conjugated materials.

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Language(s): eng - English
 Dates: 2014-10-312014-12-182015-01-16
 Publication Status: Published in print
 Pages: 8
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000348331700029
DOI: 10.1021/jo502432e
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Title: Journal of Organic Chemistry
Source Genre: Journal
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Publ. Info: Washington, D.C., etc. : American Chemical Society [etc.]
Pages: - Volume / Issue: 80 (2) Sequence Number: - Start / End Page: 980 - 987 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967