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<p>Benzene ring-substituted bindones, 5,5′,6,6′-tetrahalo-[1,2′-biindenylidene]-1′,3,3′(2<i>H</i>)-triones (halogen is Cl, Br, F), were first synthesized by condensation of the corresponding 5,6-dihalo-1<i>H</i>-indene-1,3(2<i>H</i>)-diones. 4,5,6,7-Tetrachloro-1<i>H</i>-indene-1,3(2<i>H</i>)-dione was unreactive under the reaction conditions; however, it reacted with unsubstituted 1<i>H</i>-indene-1,3(2<i>H</i>)-dione to give 4′,5′,6′,7′-tetrachloro-[1,2′-biindenylidene]-1′,3,3′(2<i>H</i>)-trione. The reasons for this behavior were revealed using quantum mechanical calculations. The product of condensation of two different 1<i>H</i>-indene-1,3(2<i>H</i>)-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′(2<i>H</i>)-trione promising as end groups in bulk heterojunction solar cells.</p>

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

  • 期刊论文

  • 发表日期：

    2026年1月1日

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

摘要

Benzene ring-substituted bindones, 5,5′,6,6′-tetrahalo-[1,2′-biindenylidene]-1′,3,3′(2H)-triones (halogen is Cl, Br, F), were first 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′-biindenylidene]-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.