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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 Nečas Dr Reinhard P Kaiser Dr Ludovic Favereau Dr Ivana Císařová Assoc Prof Róbert Gyepes Assoc Prof Dr Jana Hodačová 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., Dolejškova 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 |