Facile synthesis of 3-thiosubstituted 9-oxo-1-hetaryl-9H-indeno[2,1-c]pyridine-4-carbonitriles as end-groups for non-fullerene acceptors

Facile synthesis of 3-thiosubstituted 9-oxo-1-hetaryl-9H-indeno[2,1-c]pyridine-4-carbonitriles as end-groups for non-fullerene acceptors Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2025, DOI: 10.1055/a-2681-5727

Authors

Usova Sofia D. ¹ , Knysh Margarita L. ¹ , Knyazeva Ekaterina A. ¹ , Mikhalchenko Ludmila V. ¹ , Rakitin Oleg Alekseevich ¹

Affiliations

1	Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation

We developed mild synthetic conditions for the formation of 3-thio-substituted 9-oxo-1-hetaryl-9H-indeno[2,1-c]pyridine-4-carbonitriles in quantitative yields via the reaction of readily available 2-(3-oxo-2-arylidene-2,3-dihydro-1H-inden-1-ylidene)malononitrile with S-nucleophiles. The developed protocol demonstrated superior efficiency to N-nucleophiles via a two-step approach compared to the known methods. The potential application of the synthesized thio-substituted 2-azafluorenones as terminal groups in non-fullerene acceptors (NFAs) for organic solar cells was successfully demonstrated. The key characteristics of these novel end-group-functionalized NFAs were evaluated and compared with well-established literature analogs.

Usova S.D. , Knysh M.L. , Knyazeva E.A. , Mikhalchenko L.V. , Rakitin O.A.
Facile synthesis of 3-thiosubstituted 9-oxo-1-hetaryl-9H-indeno[2,1-c]pyridine-4-carbonitriles as end-groups for non-fullerene acceptors
Synthesis-Stuttgart. 2025. DOI: 10.1055/a-2681-5727 WOS Scopus OpenAlex

Web of science:	WOS:001586843400001
Scopus:	2-s2.0-105018617311
OpenAlex:	W4413210053

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