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Issue 36, 2014
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Tetracyano isoindigo small molecules and their use in n-channel organic field-effect transistors

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Abstract

N,N′-Dihexyl-6,6′-dicyanoisoindigo, N,N′-didecyl-5,5′,6,6′-tetracyanoisoindigo, N,N′-dihexyl-5,5′,6,6′-tetracyanoisoindigo, and N,N′-dihexyl-5,5′,6,6′-tetracyanothienoisoindigo have been synthesised in moderate yields by the reaction of corresponding di and tetrabromo species with CuCN, with microwave heating leading to higher yields and fewer side products for the tetrasubstituted species. Di- and tetracyano substitution anodically shifts the molecular reduction potential relative to the unsubstituted cores by ca. 0.4 and 0.8 V, respectively, with the resultant values for the tetracyano derivatives (−0.58 to −0.67 V vs. FeCp2+/0) suggesting the possibility of air-stable electron transport. All the synthesised cyano derivatives operate in n-channel OFETs, while the tetrabromothienoisoindigo derivative functions in a p-channel transistor. The tetracyanothienoisoindigo derivative exhibits the highest field-effect electron mobility values – up to 0.04 and 0.09 cm2 V−1 s−1 in spin-coated and inkjet-printed devices respectively – and OFETs incorporating this compound have been shown to operate in air without significant degradation of their mobility values in the saturation regime.

Graphical abstract: Tetracyano isoindigo small molecules and their use in n-channel organic field-effect transistors

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Supplementary files

Article information


Submitted
02 Jun 2014
Accepted
29 Jul 2014
First published
07 Aug 2014

Phys. Chem. Chem. Phys., 2014,16, 19345-19350
Article type
Paper

Tetracyano isoindigo small molecules and their use in n-channel organic field-effect transistors

R. R. Dasari, A. Dindar, C. K. Lo, C. Wang, C. Quinton, S. Singh, S. Barlow, C. Fuentes-Hernandez, J. R. Reynolds, B. Kippelen and S. R. Marder, Phys. Chem. Chem. Phys., 2014, 16, 19345
DOI: 10.1039/C4CP02427C

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