Our paper “Dinaphtho[1,2‑b:2′,1’‑d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π‑Electronic Cores” is available online in Chemistry of Materials.
Dinaphtho[1,2‑b:2′,1’‑d]chalcogenophenes: Comprehensive Investigation of the Effect of the Chalcogen Atoms in the Phenacene-Type π‑Electronic Cores
C. Mitsui, T. Okamoto*, H. Matsui, M. Yamagishi, T. Matsushita, J. Soeda, K. Miwa, H. Sato, A. Yamano, T. Uemura, and J. Takeya*
Chem. Mater. 25, 3952−3956 (2013).
We report dinaphtho[1,2-b:2′,1′-d]chalcogenophenes as a new class of highly potential p-type semiconductors. As the result of comprehensive investigations including computational studies based on single-crystal structures successfully determined by X-ray analysis, the impacts of the chalcogen atoms are substantially manifested in their molecular orbitals, crystal packing structures, charge-transporting properties, and the device performances at the end. Among them, dinaphtho[1,2-b:2′,1′-d]thiophene and dinaphtho[1,2-b:2′,1′-d]selenophene achieved a hole mobility of up to 1.6 and 2.0 cm2 V–1 s–1, respectively, accompanied by an Ion/Ioff ratio as high as 104–105 in their single-crystal organic field-effect transistors. Such high performances are attributed to the large orbital coefficient on the chalcogen atoms and the ideal packing structures induced by chalcogen-bridged W-shaped molecules.