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

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. Copyright © 2020 American Chemical Society.Russian Foundation for Basic Research, RFBR: 18-33-00103-mol_aRussian Science Foundation, RSF: 18-13-00409The research was financially supported by the Russian Science Foundation (project no. 18-13-00409). Y.A.K would like to acknowledge the financial support for the part of the synthetic section from the Russian Foundation for Basic Research (research project no. 18-33-00103-mol_a). The authors are grateful to Grigory A. Kim for carrying out the DFT calculations, which were performed by using “Uran” supercomputer of the Institute of Mathematics and Mechanics of the Ural Branch of the Russian Academy of Sciences. NMR experiments were carried out by using equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences