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Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes |
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| Authors: | Dr Timothée Cadart Dr David Ne?as Dr Reinhard P Kaiser Dr Ludovic Favereau Dr Ivana Císa?ová Assoc?Prof Róbert Gyepes Assoc?Prof?Dr Jana Hoda?ová Assoc?Prof?Dr Květa Kalíková Dr Lucie Bednárová Dr Jeanne Crassous Prof?Dr Martin Kotora |
| Institution: | 1. Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic;2. Université de Rennes, CNRS, ISCR-UMR 6226, 35000 Rennes, France;3. Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic;4. Academy of Sciences of the Czech Republic, J. Heyrovský Institute of Physical Chemistry, v.v.i., Dolej?kova 2155/3, 182 23 Praha 8, Czech Republic;5. Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, 166 28 Praha 6, Czech Republic;6. Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic;7. Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, 166 10 Prague 6, Czech Republic |
| Abstract: | The enantioselective synthesis of chiral 7]-helical dispirodihydro2,1-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). |
| Keywords: | catalysis circularly polarized luminescence enantioselective cyclotrimerization helical compounds indenofluorene |