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

0542907 - ÚFCH JH 2022 RIV DE eng J - Článek v odborném periodiku
Cadart, T. - Nečas, D. - Kaiser, R. P. - Favereau, L. - Císařová, I. - Gyepes, Robert - Hodačová, J. - Kalíková, K. - Bednárová, Lucie - Crassous, J. - Kotora, M.
Rhodium-Catalyzed Enantioselective Synthesis of Highly Fluorescent and CPL-Active Dispiroindeno[2,1-c]fluorenes.
Chemistry - A European Journal. Roč. 27, č. 44 (2021), s. 11279-11284. ISSN 0947-6539. E-ISSN 1521-3765
Institucionální podpora: RVO:61388955 ; RVO:61388963
Klíčová slova: circularly-polarized electroluminescence * photophysical properties * intramolecular 2+2+2 * 2+1+2+1 cycloadditions * dibenzohelicenes * chromatography * fluorenols * helicenes * molecules * catalysis * circularly polarized luminescence * enantioselective cyclotrimerization * helical compounds * indenofluorene
Obor OECD: Physical chemistry; Analytical chemistry (UOCHB-X)
Impakt faktor: 5.020, rok: 2021
Způsob publikování: Omezený přístup

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).
Trvalý link: http://hdl.handle.net/11104/0321723