Dibenzo[ f,h]furazano[3,4- b]quinoxalines: Synthesis by Intramolecular Cyclization through Direct Transition Metal-Free C-H Functionalization and Electrochemical, Photophysical, and Charge Mobility Characterization

Yuriy A Kvashnin; Egor V Verbitskiy; Oleg S Eltsov; Pavel A Slepukhin; Alexey R Tameev; Natalia V Nekrasova; Gennady L Rusinov; Jean-Michel Nunzi; Oleg N Chupakhin; Valery N Charushin

doi:10.1021/acsomega.0c00479

Dibenzo[ f,h]furazano[3,4- b]quinoxalines: Synthesis by Intramolecular Cyclization through Direct Transition Metal-Free C-H Functionalization and Electrochemical, Photophysical, and Charge Mobility Characterization

ACS Omega. 2020 Mar 30;5(14):8200-8210. doi: 10.1021/acsomega.0c00479. eCollection 2020 Apr 14.

Authors

Yuriy A Kvashnin¹, Egor V Verbitskiy^{1

2}, Oleg S Eltsov², Pavel A Slepukhin^{1

2}, Alexey R Tameev^{1

3}, Natalia V Nekrasova³, Gennady L Rusinov^{1

2}, Jean-Michel Nunzi⁴, Oleg N Chupakhin^{1

2}, Valery N Charushin^{1

2}

Affiliations

¹ Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Street 22, Ekaterinburg, 620108, Russia.
² Ural Federal University, Mira Street 19, Ekaterinburg, 620002, Russia.
³ Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, Leninsky Prospekt, 31 bld. 4, Moscow, 119071, Russia.
⁴ Department of Physics, Engineering Physics and Astronomy, Department of Chemistry, 90 Bader Lane, Queens University, Kingston, Ontario K7L-3N6, Canada.

Abstract

Herein, we describe the synthesis of unsymmetrically substituted dibenzo[f,h]furazano[3,4-b]quinoxalines by intramolecular cyclization through direct transition metal-free C-H functionalization. The electrochemical and photophysical properties for several polycycles have been measured. In thin films of the dibenzo[f,h]furazano[3,4-b]quinoxalines, hole mobility is in the order of 10^-4 cm² V^-1 s^-1. The results show that the HOMO and LUMO energy levels are appropriate for using the compounds as hole-transport materials in thin-film devices, in particular, organic and perovskite solar cells.