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Synthesis
DOI: 10.1055/a-2681-5727
Paper

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

Sofia D. Usova
1   Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Margarita L. Knysh
1   Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Ekaterina A. Knyazeva
1   Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Ludmila V. Mikhalchenko
1   Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
,
Oleg Alekseevich Rakitin 
1   Laboratory of Polysulphur-Nitrogen Heterocycles (N31), FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, Russian Federation (Ringgold ID: RIN68429)
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Supported by: Russian Science Foundation 24-23-00026
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We developed mild synthetic conditions for the formation of 3-thiosubstituted 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.



Publication History

Received: 05 May 2025

Accepted after revision: 11 August 2025

Accepted Manuscript online:
11 August 2025

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