Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
18-17823S
Grantová Agentura České Republiky
PubMed
33830567
DOI
10.1002/chem.202100759
Knihovny.cz E-zdroje
- Klíčová slova
- catalysis, circularly polarized luminescence, enantioselective cyclotrimerization, helical compounds, indenofluorene,
- MeSH
- fluoreny MeSH
- katalýza MeSH
- luminiscence MeSH
- rhodium * MeSH
- stereoizomerie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- fluoreny MeSH
- rhodium * MeSH
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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