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Article Dans Une Revue Chemistry - A European Journal Année : 2021

Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes

Résumé

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 (R) complex. Further transformations led to the corresponding DSF-IFs. The prepared helically chiral DSF-IFs combine circularly polarized luminescence (CPL) activity (g(lum)=similar to 10(-3)) with exceptionally high fluorescence quantum yields (up to phi(lum)=0.97).
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Dates et versions

hal-03245247 , version 1 (11-06-2021)

Identifiants

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Timothee Cadart, David Necas, Reinhard P. Kaiser, Ludovic Favereau, Ivana Cisarova, et al.. Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes. Chemistry - A European Journal, 2021, 27 (44), pp.11279-11284. ⟨10.1002/chem.202100759⟩. ⟨hal-03245247⟩
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