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Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes.
Cadart, Timothée; Necas, David; Kaiser, Reinhard P; Favereau, Ludovic; Císarová, Ivana; Gyepes, Róbert; Hodacová, Jana; Kalíková, Kveta; Bednárová, Lucie; Crassous, Jeanne; Kotora, Martin.
Afiliación
  • Cadart T; Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
  • Necas D; Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
  • Kaiser RP; Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
  • Favereau L; Université de Rennes, CNRS, ISCR-UMR 6226, 35000, Rennes, France.
  • Císarová I; Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
  • Gyepes R; Academy of Sciences of the Czech Republic, J. Heyrovský Institute of Physical Chemistry, v.v.i., Dolejskova 2155/3, 182 23, Praha 8, Czech Republic.
  • Hodacová J; Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28, Praha 6, Czech Republic.
  • Kalíková K; Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
  • Bednárová L; Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, 166 10, Prague 6, Czech Republic.
  • Crassous J; Université de Rennes, CNRS, ISCR-UMR 6226, 35000, Rennes, France.
  • Kotora M; Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Praha 2, Czech Republic.
Chemistry ; 27(44): 11279-11284, 2021 Aug 05.
Article en En | MEDLINE | ID: mdl-33830567
The enantioselective synthesis of chiral [7]-helical dispirodihydro[2,1-c]indenofluorenes (DSF-IFs) was achieved for the first time in good yields with high er values (er up to 99 : 1). The crucial step of the whole reaction sequence was the enantioselective intramolecular [2+2+2] cycloaddition of tethered triynediols to indenofluorenediols, which was catalyzed by a Rh/SEGPHOS® complex. Further transformations led to the corresponding DSF-IFs. The prepared helically chiral DSF-IFs combine circularly polarized luminescence (CPL) activity (glum =∼10-3 ) with exceptionally high fluorescence quantum yields (up to Φlum =0.97).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Rodio Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: República Checa Pais de publicación: Alemania
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Rodio Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: República Checa Pais de publicación: Alemania