Cargando…

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

[Image: see text] 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 measu...

Descripción completa

Detalles Bibliográficos
Autores principales: Kvashnin, Yuriy A., Verbitskiy, Egor V., Eltsov, Oleg S., Slepukhin, Pavel A., Tameev, Alexey R., Nekrasova, Natalia V., Rusinov, Gennady L., Nunzi, Jean-Michel, Chupakhin, Oleg N., Charushin, Valery N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7161064/
https://www.ncbi.nlm.nih.gov/pubmed/32309730
http://dx.doi.org/10.1021/acsomega.0c00479
_version_ 1783522881969324032
author Kvashnin, Yuriy A.
Verbitskiy, Egor V.
Eltsov, Oleg S.
Slepukhin, Pavel A.
Tameev, Alexey R.
Nekrasova, Natalia V.
Rusinov, Gennady L.
Nunzi, Jean-Michel
Chupakhin, Oleg N.
Charushin, Valery N.
author_facet Kvashnin, Yuriy A.
Verbitskiy, Egor V.
Eltsov, Oleg S.
Slepukhin, Pavel A.
Tameev, Alexey R.
Nekrasova, Natalia V.
Rusinov, Gennady L.
Nunzi, Jean-Michel
Chupakhin, Oleg N.
Charushin, Valery N.
author_sort Kvashnin, Yuriy A.
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-7161064
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-71610642020-04-17 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 Kvashnin, Yuriy A. Verbitskiy, Egor V. Eltsov, Oleg S. Slepukhin, Pavel A. Tameev, Alexey R. Nekrasova, Natalia V. Rusinov, Gennady L. Nunzi, Jean-Michel Chupakhin, Oleg N. Charushin, Valery N. ACS Omega [Image: see text] 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. American Chemical Society 2020-03-30 /pmc/articles/PMC7161064/ /pubmed/32309730 http://dx.doi.org/10.1021/acsomega.0c00479 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kvashnin, Yuriy A.
Verbitskiy, Egor V.
Eltsov, Oleg S.
Slepukhin, Pavel A.
Tameev, Alexey R.
Nekrasova, Natalia V.
Rusinov, Gennady L.
Nunzi, Jean-Michel
Chupakhin, Oleg N.
Charushin, Valery N.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7161064/
https://www.ncbi.nlm.nih.gov/pubmed/32309730
http://dx.doi.org/10.1021/acsomega.0c00479
work_keys_str_mv AT kvashninyuriya dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT verbitskiyegorv dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT eltsovolegs dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT slepukhinpavela dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT tameevalexeyr dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT nekrasovanataliav dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT rusinovgennadyl dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT nunzijeanmichel dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT chupakhinolegn dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization
AT charushinvaleryn dibenzofhfurazano34bquinoxalinessynthesisbyintramolecularcyclizationthroughdirecttransitionmetalfreechfunctionalizationandelectrochemicalphotophysicalandchargemobilitycharacterization