Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules

Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2021, Volume: 6, Number: 24, Pages: 6043-6049 Pages count : 7 DOI: 10.1002/slct.202101491

Tags

Electron-deficient compounds; Fused-ring systems; Polycycles; Solar Cells; Sulfur heterocycles

Authors

Baranov Denis S. ¹ , Nevostruev Danil A. ¹ , Kazantsev Maxim S. ^2,3 , Zinoviev Vladimir A. ⁴ , Zelentsova Ekaterina A. ^2,5 , Dmitriev Alexey A. ¹ , Gritsan Nina P. ¹ , Tsentalovich Yuri P. ^2,5 , Kotova Maria ⁶ , Düreth Johannes ⁶ , Sperlich Andreas Andreas ⁶ , Dyakonov Vladimir Vladimir ⁶ , Kulik Leonid V. ¹

Affiliations

1	Siberian Branch of the Russian Academy of Sciences, Voevodsky Institute of Chemical Kinetics and Combustion, Novosibirsk, 630090, Russian Federation
2	Novosibirsk State University, Novosibirsk, 630090, Russian Federation
3	Siberian Branch of the Russian Academy of Sciences, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk, 630090, Russian Federation
4	Siberian Branch of the Russian Academy of Science, Rzhanov Institute of Semiconductor Physics, Novosibirsk, 630090, Russian Federation
5	Siberian Branch of the Russian Academy of Science, International Tomography Center, Novosibirsk, 630090, Russian Federation
6	Experimental Physics 6, University of Würzburg, Würzburg, 97074, Germany

Two acceptor small molecules consisting of 2-(11-oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile frameworks connected by a bis(thiophen-2-ylethynyl)arene bridge were synthesized by the two-step sequence of Sonogashira cross-coupling and Knoevenagel condensation in order to investigate their performance as non-fullerene acceptors in organic solar cells. Optical, electrochemical and photovoltaic properties of new 2,2′-[2,2′-(5,5′-(arenediyl)bis(ethyne-2,1-diyl)bis(thien-5,2-diyl))bis(11-oxoanthra[2,1-b]thiophen-6-ylidene)]dipropanedinitriles and previously studied analogs of 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were compared to assess the effect of introducing ethynylthiophene units between the arene linker and the 2-(11-oxoanthrathiophen-6-ylidene)propanedinitrile units. Despite the proper energy level alignment and morphology, composites of the newly synthesized compounds with the PBDB-T donor polymer demonstrate a moderate PCE of 0.54 %. The small value of the short circuit current as compared to composites with fullerene acceptors is probably due to the low electron mobility in the newly synthesized compounds. The low electron mobility, in turn, is probably cause by the LUMO localization at the edge units of the acceptor-type molecules, in contrast to the almost uniform LUMO delocalization over the whole π-conjugated system for high-performing non-fullerene acceptors such as ITIC. © 2021 Wiley-VCH GmbH

Baranov D.S. , Nevostruev D.A. , Kazantsev M.S. , Zinoviev V.A. , Zelentsova E.A. , Dmitriev A.A. , Gritsan N.P. , Tsentalovich Y.P. , Kotova M. , Düreth J. , Sperlich Andreas A. , Dyakonov Vladimir V. , Kulik L.V.
Synthesis, Characterization and Photovoltaic Properties of Electron-Accepting (11-Oxoanthra[2,1-b]thiophen-6-ylidene)dipropanedinitrile-Based Molecules
ChemistrySelect. 2021. V.6. N24. P.6043-6049. DOI: 10.1002/slct.202101491 WOS Scopus

Web of science	WOS:000674320500026
Scopus	2-s2.0-85110522112
OpenAlex	W3175975457