Gold-catalyzed synthesis of π-extended carbazole-based systems and their application as organic semiconductors

Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties - namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and th...

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Main Authors: Hendrich, Christoph (Author) , Hannibal, Valentin D. (Author) , Eberle, Lukas (Author) , Hertwig, Leif E. (Author) , Zschieschang, Ute (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Klauk, Hagen (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 01 February 2021
In: Advanced synthesis & catalysis
Year: 2021, Volume: 363, Issue: 5, Pages: 1401-1407
ISSN:1615-4169
DOI:10.1002/adsc.202001461
Online Access:Resolving-System, kostenfrei, Volltext: https://doi.org/10.1002/adsc.202001461
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202001461
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Author Notes:Christoph M. Hendrich, Valentin D. Hannibal, Lukas Eberle, Leif E. Hertwig, Ute Zschieschang, Frank Rominger, Matthias Rudolph, Hagen Klauk, and A. Stephen K. Hashmi
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Summary:Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties - namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and the gold-catalyzed key step comprises of a cascade reaction starting from stable di-azido compounds. The obtained molecules were fully characterized and their optical and electronic properties as well as their performance in organic thin-film transistors generated by vacuum deposition were studied. Charge-carrier mobilities of up to 0.3 cm2/Vs were measured.
Item Description:Version of record online: Februar 1, 2021
Gesehen am 07.05.2021
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.202001461