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 cm 2 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.

Molecular Dynamics and Conductivity of a PTB7:PC71BM Photovoltaic Polymer Blend: A Dielectric Spectroscopy Study

“…The charge mobility was measured by using the charge extraction by linearly increasing the voltage (CELIV) technique according to the procedure described earlier. , The structure of the samples was ITO (100 nm)/SiO 2 (70 nm)/active layer (70–90 nm)/Au­(100 nm). A SiO 2 insulator layer was deposited onto the ITO/glass substrate by conventional magnetron sputtering.…”

Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts

“…1,2,5-Chalcogenadiazoles and their annulated derivatives have received great attention due to the remarkable combination of their interesting properties, synthesis, and applications in materials sciences [32][33][34][35]. Recently, some of us designed and demonstrated the possible applications of [1,2,5]oxadiazolo [3,4-b]pyrazine derivatives (also called furazanopyrazines) as effective multifunctional chemosensors (I) [36,37], charge-transport materials for photovoltaics (II) [38], and compounds with advanced nonlinear optical (NLO) properties (III) (Figure 2) [39]. Phenylene bridges are typical linkers in push-pull structures, even if the aromaticity of the π-linker is directed toward the ICT [40,41].…”

A co-crystal of heterobicyclic isomers as a product of the cyclocondensation reaction of 3,4-diaminofurazan with diethyl-2-oxosuccinate

“…[2][3][4][5][6][7][8][9][10] Significant progress has been achieved in the medicinal chemistry of furazanopyrazines. [11][12][13][14][15] In recent years, some derivatives of this fused bicycle have also found use as organic semiconductors, [16][17][18][19][20][21][22][23][24] fluorescent sensors 25 and even organic magnets. [26][27][28] The fact that research on furazanopyrazines has remained a topic of great interest for more than 50 years confirms the high relevance of their study.…”