Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes
- Resource Type
- Authors
- Květa Kalíková; Ludovic Favereau; Róbert Gyepes; Lucie Bednárová; David Nečas; Jana Hodačová; Ivana Císařová; Reinhard P. Kaiser; Timothée Cadart; Jeanne Crassous; Martin Kotora
- Source
- Chemistry-A European Journal
Chemistry-A European Journal, Wiley-VCH Verlag, 2021, ⟨10.1002/chem.202100759⟩
Chemistry-A European Journal, 2021, 27 (44), pp.11279-11284. ⟨10.1002/chem.202100759⟩
- Subject
- Luminescence
Stereochemistry
chemistry.chemical_element
010402 general chemistry
01 natural sciences
helical compounds
Catalysis
Rhodium
chemistry.chemical_compound
[CHIM]Chemical Sciences
Fluorenes
SEGPHOS
catalysis
010405 organic chemistry
Organic Chemistry
Enantioselective synthesis
Stereoisomerism
circularly polarized luminescence
General Chemistry
Fluorescence
Cycloaddition
0104 chemical sciences
enantioselective cyclotrimerization
chemistry
Intramolecular force
indenofluorene
- Language
- English
- ISSN
- 0947-6539
1521-3765
International audience; 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).