Thienoacene-fused pentalenes: Syntheses, structures, physical properties and applications for organic field-effect transistors

Abstract
Three soluble and stable thienoacene-fused pentalene derivatives (1-3) with different π-conjugation lengths were synthesized. X-ray crystallographic analysis and density functional theory (DFT) calculations revealed their unique geometric and electronic structures due to the interaction between the aromatic thienoacene units and antiaromatic pentalene moiety. As a result, they all possess a small energy gap and show amphoteric redox behaviour. Time dependent (TD) DFT calculations were used to explain their unique electronic absorption spectra. These new compounds exhibited good thermal stability and ordered packing in solid state and thus their applications in organic field-effect transistors (OFETs) were also investigated. The highest field-effect hole mobility of 0.016, 0.036 and 0.001 cm2 V-1 s-1 was achieved for solution-processed thin films of 1-3, respectively.

Citation
Dai, G., Chang, J., Shi, X., Zhang, W., Zheng, B., Huang, K.-W., & Chi, C. (2014). Thienoacene-Fused Pentalenes: Syntheses, Structures, Physical Properties and Applications for Organic Field-Effect Transistors. Chemistry - A European Journal, 21(5), 2019–2028. doi:10.1002/chem.201405652

Acknowledgements
C.C. acknowledges financial support from MOE AcRF Tier 1 grants R-143-000-510-112, R-143-000-573-112 and NUS start up grant R-143-000-486-133. K.W.H. acknowledges financial support from KAUST.

Publisher
Wiley

Journal
Chemistry - A European Journal

DOI
10.1002/chem.201405652

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