Synthesis and properties of benzene ring-substituted [1,2′-biindenylidene]-1′,3,3′(2H)-triones

Synthesis and properties of benzene ring-substituted [1,2′-biindenylidene]-1′,3,3′(2H)-triones Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2026, Volume: 75, Number: 1, Pages: 196-203 Pages count : 8 DOI: 10.1007/s11172-026-4875-8

Tags

[1,2´-biindenylidene]-1´,3,3´(2H)-trione, synthesis, dimerization, bulk heterojunction solar cells, 1H-indene-1,3(2H)-diones, UV-vis spectra of dyes.

Authors

Usova S.D. ¹ , Knysh M.I. ^1,2 , Golovanov I.S. ¹ , Pospelov E.V. ¹ , Knyazeva E.A. ¹ , Rakitin O.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Dmitry Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047 Moscow, Russian Federation

Benzene ring-substituted bindones, 5,5´,6,6´-tetrahalo-[1,2´-biindenylidene]- 1´,3,3´(2H)-triones (halogen is Cl, Br, F), were fi rst synthesized by condensation of the corresponding 5,6-dihalo-1H-indene-1,3(2H)-diones. 4,5,6,7-Tetrachloro-1H-indene-1,3(2H)-dione was unreactive under the reaction conditions; however, it reacted with unsubstituted 1H-indene-1,3(2H)-dione to give 4´,5´,6´,7´-tetrachloro-[1,2´-bi indenylidene]- 1´,3,3´(2H)-trione. The reasons for this behavior were revealed using quantum mechanical calculations. The product of condensation of two different 1H-indene-1,3(2H)- diones showed an intense absorption maximum at 505 nm absent or very weak in the case of the symmetrical bindones thus indicating the intramolecular charge transfer between unsubstituted benzene ring and electron-withdrawing tetrachlorobenzene moiety. The discovered properties make 4´,5´,6´,7´-tetrachloro-[1,2´-biindenylidene]-1´,3,3´(2H)- trione promising as end groups in bulk heterojunction solar cells.

Usova S.D. , Knysh M.I. , Golovanov I.S. , Pospelov E.V. , Knyazeva E.A. , Rakitin O.A.
Synthesis and properties of benzene ring-substituted [1,2′-biindenylidene]-1′,3,3′(2H)-triones
Russian Chemical Bulletin. 2026. V.75. N1. P.196-203. DOI: 10.1007/s11172-026-4875-8 Scopus OpenAlex

Усова С.Д. , Кныш М.И. , Голованов И.С. , Поспелов И.В. , Князева Е.А. , Ракитин О.А.
Синтез и свойства замещенных в бензольном кольце [1,2´-биинденилиден]-1´,3,3´(2H)-трионов
Известия Академии наук. Серия химическая. 2026. Т.75. №1. С.196-203.

Submitted:	Jun 3, 2025
Accepted:	Jul 15, 2025
Published online:	Dec 10, 2025

≡ Scopus:	2-s2.0-105034870638
≡ OpenAlex:	W7144240233