12Н-quinoxaline[2,3-b]phenoxazines: Synthesis, optical, electrochemical properties and insight into photovoltaic application

Eugeny P. Ivakhnenko; Pavel A. Knyazev; Nikolay I. Omelichkin; Nadezhda I. Makarova; Andrey G. Starikov; Alexey E. Aleksandrov; Artem V. Ezhov; Alexey R. Tameev; Oleg P. Demidov; Vladimir I. Minkin

doi:10.1016/j.dyepig.2021.109848

12Н-quinoxaline[2,3-b]phenoxazines: Synthesis, optical, electrochemical properties and insight into photovoltaic application

Eugeny P. Ivakhnenko, Pavel A. Knyazev, Nikolay I. Omelichkin, Nadezhda I. Makarova, Andrey G. Starikov, Alexey E. Aleksandrov, Artem V. Ezhov, Alexey R. Tameev, Oleg P. Demidov, Vladimir I. Minkin

Research output: Contribution to journal › Article › peer-review

Abstract

A series of N-aryl derivatives of heteropentacyclic 12Н-quinoxaline[2,3-b]phenoxazine (QOPO) system were synthesized and spectral, luminescent, electrochemical and optoelectronic properties of the prepared compounds studied. The compounds are well soluble in nonpolar and polar solvents, absorb in the strongest emissive part of the solar spectrum and exhibit sufficiently high photostability at air conditions. The HOMO, LUMO energy levels of the obtained QOPOs were calculated by the DFT B3LYP/6–311++G(d,p) method and assessed using the electrochemical methodology. The double-layered p-n heterojunction organic solar cells constructed on the basis of QOPOs as electron donor components, bathocuproine as the exciton blocking layer and fullerene C₆₀ as electron acceptor displayed promising values of photovoltaic (open circuit voltage and short-circuit current density) parameters.

Original language	English
Article number	109848
Journal	Dyes and Pigments
Volume	197
DOIs	https://doi.org/10.1016/j.dyepig.2021.109848
Publication status	Published - 1 Jan 2022
Externally published	Yes

Keywords

DFT calculations
Electrochemistry
Fluorescence
Organic solar cells
Photostability
Quinoxalinophenoxazines
Triphenodioxazines

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.dyepig.2021.109848

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Ivakhnenko, E. P., Knyazev, P. A., Omelichkin, N. I., Makarova, N. I., Starikov, A. G., Aleksandrov, A. E., Ezhov, A. V., Tameev, A. R., Demidov, O. P., & Minkin, V. I. (2022). 12Н-quinoxaline[2,3-b]phenoxazines: Synthesis, optical, electrochemical properties and insight into photovoltaic application. Dyes and Pigments, 197, Article 109848. https://doi.org/10.1016/j.dyepig.2021.109848

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title = "12Н-quinoxaline[2,3-b]phenoxazines: Synthesis, optical, electrochemical properties and insight into photovoltaic application",

abstract = "A series of N-aryl derivatives of heteropentacyclic 12Н-quinoxaline[2,3-b]phenoxazine (QOPO) system were synthesized and spectral, luminescent, electrochemical and optoelectronic properties of the prepared compounds studied. The compounds are well soluble in nonpolar and polar solvents, absorb in the strongest emissive part of the solar spectrum and exhibit sufficiently high photostability at air conditions. The HOMO, LUMO energy levels of the obtained QOPOs were calculated by the DFT B3LYP/6–311++G(d,p) method and assessed using the electrochemical methodology. The double-layered p-n heterojunction organic solar cells constructed on the basis of QOPOs as electron donor components, bathocuproine as the exciton blocking layer and fullerene C60 as electron acceptor displayed promising values of photovoltaic (open circuit voltage and short-circuit current density) parameters.",

keywords = "DFT calculations, Electrochemistry, Fluorescence, Organic solar cells, Photostability, Quinoxalinophenoxazines, Triphenodioxazines",

author = "Ivakhnenko, \{Eugeny P.\} and Knyazev, \{Pavel A.\} and Omelichkin, \{Nikolay I.\} and Makarova, \{Nadezhda I.\} and Starikov, \{Andrey G.\} and Aleksandrov, \{Alexey E.\} and Ezhov, \{Artem V.\} and Tameev, \{Alexey R.\} and Demidov, \{Oleg P.\} and Minkin, \{Vladimir I.\}",

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year = "2022",

month = jan,

day = "1",

doi = "10.1016/j.dyepig.2021.109848",

language = "English",

volume = "197",

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T1 - 12Н-quinoxaline[2,3-b]phenoxazines

T2 - Synthesis, optical, electrochemical properties and insight into photovoltaic application

AU - Ivakhnenko, Eugeny P.

AU - Knyazev, Pavel A.

AU - Omelichkin, Nikolay I.

AU - Makarova, Nadezhda I.

AU - Starikov, Andrey G.

AU - Aleksandrov, Alexey E.

AU - Ezhov, Artem V.

AU - Tameev, Alexey R.

AU - Demidov, Oleg P.

AU - Minkin, Vladimir I.

PY - 2022/1/1

Y1 - 2022/1/1

N2 - A series of N-aryl derivatives of heteropentacyclic 12Н-quinoxaline[2,3-b]phenoxazine (QOPO) system were synthesized and spectral, luminescent, electrochemical and optoelectronic properties of the prepared compounds studied. The compounds are well soluble in nonpolar and polar solvents, absorb in the strongest emissive part of the solar spectrum and exhibit sufficiently high photostability at air conditions. The HOMO, LUMO energy levels of the obtained QOPOs were calculated by the DFT B3LYP/6–311++G(d,p) method and assessed using the electrochemical methodology. The double-layered p-n heterojunction organic solar cells constructed on the basis of QOPOs as electron donor components, bathocuproine as the exciton blocking layer and fullerene C60 as electron acceptor displayed promising values of photovoltaic (open circuit voltage and short-circuit current density) parameters.

AB - A series of N-aryl derivatives of heteropentacyclic 12Н-quinoxaline[2,3-b]phenoxazine (QOPO) system were synthesized and spectral, luminescent, electrochemical and optoelectronic properties of the prepared compounds studied. The compounds are well soluble in nonpolar and polar solvents, absorb in the strongest emissive part of the solar spectrum and exhibit sufficiently high photostability at air conditions. The HOMO, LUMO energy levels of the obtained QOPOs were calculated by the DFT B3LYP/6–311++G(d,p) method and assessed using the electrochemical methodology. The double-layered p-n heterojunction organic solar cells constructed on the basis of QOPOs as electron donor components, bathocuproine as the exciton blocking layer and fullerene C60 as electron acceptor displayed promising values of photovoltaic (open circuit voltage and short-circuit current density) parameters.

KW - DFT calculations

KW - Electrochemistry

KW - Fluorescence

KW - Organic solar cells

KW - Photostability

KW - Quinoxalinophenoxazines

KW - Triphenodioxazines

UR - https://www.scopus.com/pages/publications/85116907525

U2 - 10.1016/j.dyepig.2021.109848

DO - 10.1016/j.dyepig.2021.109848

M3 - Article

AN - SCOPUS:85116907525

SN - 0143-7208

VL - 197

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 109848

ER -

12Н-quinoxaline[2,3-b]phenoxazines: Synthesis, optical, electrochemical properties and insight into photovoltaic application

Abstract

Keywords

UN SDGs

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