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Chemistry. 2014 May 12;20(20):5938-45. doi: 10.1002/chem.201304914. Epub 2014 Apr 23.

Synthesis and properties of semiconducting bispyrrolothiophenes for organic field-effect transistors.

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  • 1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL, 60607 (USA).


A series of new highly soluble bispyrrolothiophenes were synthesized from vinyl azides by using transition-metal-catalyzed C-H-bond functionalization. In addition to modifying the substituents present on the end-pyrrolothiophene moieties, the arene linker in between the two units was also varied. The solution-state properties and field-effect-transistor (FET) electrical behavior of these bispyrrolothiophenes was compared. Our investigations identified that the optical properties and oxidation potential of our compounds were dominated by the pyrrolothiophene unit with a λmax  value of approximately 400 nm and oxidation at approximately 1 V. FET devices constructed with thin films of these bispyrrolothiophenes were also fabricated by means of thin-film solution processing. One of these compounds, a bispyrrolothiophene linked with benzothiodiazole, exhibits a mobility of approximately 0.3 cm(2)  V(-1)  s(-1) and the Ion/Ioff value is greater than 10(6).

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


azides; charge transfer; field-effect transistors; heterocycles; semiconductors; thin films

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