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Stable 7,14-disubstituted-5,12-dithiapentacenes with quinoidal conjugation
(Organic Letters, American Chemical Society (ACS), 2014-07-14) [Article]
Two 7,14-disubstituted-5,12-dithiapentacenes (1 and 2) with quinoidal conjugation were synthesized. Their ground-state quinoidal structures were proven by X-ray crystallographic analysis. They showed very different electronic and optical properties from those of the corresponding pentacene derivatives with diene conjugation, and their stability was significantly improved. Organic field effect transistors based on solution processed thin films of 1 and 2 exhibited a hole mobility of up to 0.032 cm-2 V-1 s -1. © 2014 American Chemical Society.
Cyanated diazatetracene diimides with ultrahigh electron affinity for n-channel field effect transistors
(Organic Letters, American Chemical Society (ACS), 2013-03-05) [Article]
Several diazatetracene diimides with high electron affinity (up to 4.66 eV!) were prepared and well characterized. The LUMO energy level of these electron-deficient molecules was found to be closely related to their material stability. Compound 7 with ultrahigh electron affinity suffered from reduction and hydrolysis in the presence of silica gel or water. The stable compounds 3 and 6 showed n-channel FET behavior with an average electron mobility of 0.002 and 0.005 cm2 V-1 s-1, respectively, using a solution processing method. © 2013 American Chemical Society.
Stepwise cyanation of naphthalene diimide for n-channel field-effect transistors
(Organic Letters, American Chemical Society (ACS), 2012-05-25) [Article]
Stepwise cyanation of tetrabromonaphthalenediimide (NDI) 1 gave a series of cyanated NDIs 2-5 with the monocyanated NDI 2 and dicyanated NDI 3 isolated. The tri- and tetracyano- NDIs 4 and 5 show intrinsic instability toward moisture because of their extremely low-lying LUMO energy levels. The partially cyanated intermediates can be utilized as air-stable n-type semiconductors with OFET electron mobility up to 0.05 cm 2 V -1 s -1. © 2012 American Chemical Society.
Incorporating TCNQ into thiophene-fused heptacene for n-channel field effect transistor
(Organic Letters, American Chemical Society (ACS), 2012-05-11) [Article]
Incorporation of electron-deficient tetracyanoquinodimethane (TCNQ) into electron-rich thiophene-fused heptacene was successfully achieved for the purpose of stabilizing longer acenes and generating new n-type organic semiconductors. The heptacene-TCNQ derivative 1 was found to have good stability and an expected electron transporting property. Electron mobility up to 0.01 cm 2 V -1 s -1 has been obtained for this novel material in solution processed organic field effect transistors. © 2012 American Chemical Society.
Thiophene-fused tetracene diimide with low band gap and ambipolar behavior
(Organic Letters, American Chemical Society (ACS), 2011-11-18) [Article]
The first tetracene diimide derivative fused with four thiophene rings, TT-TDI, was synthesized by an FeCl3 mediated oxidative cyclodehydrogenation reaction. TT-TDI exhibited a low band gap of 1.52 eV and amphoteric redox behavior. TT-TDI also showed a liquid crystalline property and ambipolar charge transport in thin film field-effect transistors. © 2011 American Chemical Society.