Dyes for photoelectronics based on (12H-quinoxalino[2,3-B]phenoxazinyl)phenyl derivatives

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Abstract

The acylation reactions of 4-(2,4-di-tert-butyl-10-methoxy-12H-quinoxalino[2,3-b]phenoxazin-12-yl)aniline with acid chlorides of various structures, including substituents with the properties of anchor groups (hydroxyphenyl, carboxyl, acrylamide, methacrylamide), as well as isobenzofuran-1,3-dione and dihydrofuran-2,5-dione led to the formation of the corresponding 4-(2,4-di-tert-butyl-10-methoxy-12H-quinoxalino[2,3-b]phenoxazin-12-yl)anilides in high yield (79–92%). The resulting amides were characterized by strong (ε = 2.94–4.26∙104 M–1·cm–1) absorption bands in the range of 470–630 nm with maxima at 548–551 nm. They also exhibit a photovoltaic effect and high open-circuit parameters (up to 0.57 V) in DSSC solar cells and the ability to exhibit photodiode properties.

About the authors

E. P. Ivakhnenko

Institute of Physical and Organic Chemistry, Southern Federal University

Email: ivakhnenko@sfedu.ru
Rostov-on-Don, 344091 Russia

N. I. Omelichkin

Institute of Physical and Organic Chemistry, Southern Federal University

Rostov-on-Don, 344091 Russia

P. A. Knyazev

Institute of Physical and Organic Chemistry, Southern Federal University

Rostov-on-Don, 344091 Russia

S. E. Kislicin

Institute of Physical and Organic Chemistry, Southern Federal University

Rostov-on-Don, 344091 Russia

A. V. Chernyshev

Institute of Physical and Organic Chemistry, Southern Federal University

Rostov-on-Don, 344091 Russia

A. E. Aleksandrov

A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Moscow, 119071 Russia

A. R. Tameev

A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Moscow, 119071 Russia

V. I. Minkin

Institute of Physical and Organic Chemistry, Southern Federal University

Rostov-on-Don, 344091 Russia

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