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Halogenated phenazinothiadiazoles: electron-transporting materials

Triisopropylsilyl-(TIPS)-alkynylated phenazinothiadiazoles were prepared by the condensation of halogenated ortho-quinones and TIPS-alkynylated 5,6-diamino-2,1,3-benzothiadiazole with different combinations of halogen substituents. The compounds pack in brickwall motif of head-to-head dimers featuri...

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Main Authors: Zong, Wansheng (Author) , Hippchen, Nikolai (Author) , Dittmar, Benedikt (Author) , Elter, Maximilian (Author) , Ludwig, Philipp (Author) , Rominger, Frank (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: December 2023
In: Asian journal of organic chemistry
Year: 2023, Volume: 12, Issue: 12, Pages: 1-7
ISSN:2193-5815
DOI:10.1002/ajoc.202300462
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ajoc.202300462
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ajoc.202300462
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Author Notes:Wansheng Zong, Nikolai Hippchen, Benedikt Dittmar, Maximilian Elter, Philipp Ludwig, Frank Rominger, Jan Freudenberg, and Uwe H.F. Bunz
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Summary:Triisopropylsilyl-(TIPS)-alkynylated phenazinothiadiazoles were prepared by the condensation of halogenated ortho-quinones and TIPS-alkynylated 5,6-diamino-2,1,3-benzothiadiazole with different combinations of halogen substituents. The compounds pack in brickwall motif of head-to-head dimers featuring intermolecular S−N contacts and short π-π distances, suggesting their suitability as n-channel materials in organic thin film transistors. The halogenated phenazinothiadiazoles show electron mobilities μmax ranging between 0.14 cm2 V−1 s−1 and 0.76 cm2 V−1 s−1.
Item Description:Version des Artikels: November 20, 2023
Gesehen am 10.01.2024
Physical Description:Online Resource
ISSN:2193-5815
DOI:10.1002/ajoc.202300462

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