Počet záznamů: 1
Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene
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SYSNO ASEP 0539547 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene Tvůrce(i) Shyam Sundar, Mothuku (UOCHB-X) ORCID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Bednárová, Lucie (UOCHB-X) RID, ORCID
Muller, G. (US)Zdroj.dok. European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2021, č. 1 (2021), s. 146-150Poč.str. 5 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova chiral HPLC ; circular dichroism ; helicenes ; heterohelicenes ; enantiomers ; optical properties Obor OECD Organic chemistry Způsob publikování Omezený přístup Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000596696600001 EID SCOPUS 85097318063 DOI 10.1002/ejoc.202001177 Anotace Herein, we report a simple and efficient approach to synthesize a functionalized 2,18-dimethoxy-5,10,15-trioxa[9]helicene. It was synthesized from simple phenol building blocks using two subsequent reactions namely oxidative coupling and dehydrative cyclization or palladium mediated cyclization. The molecular integrity of the helical core was determined by single-crystal X-ray diffraction and NMR techniques. Its crystal structure showed the spontaneous resolution which was attributed to the conglomerate formation of the same helical isomer via C−H⋅⋅⋅O and π⋅⋅⋅π or H⋅⋅⋅π interactions. Then, it was converted to racemic 2,18-dihydoxy-5,10,15-trioxa[9]helicene. Enantiomers were separated on preparative HPLC with high optical purity (>99 % ee). Based on electronic circular dichroism, the absolute configurations of dextrorotary and levorotatory antipodes were assigned as P and M, respectively. We also studied the absorption, emission and chiroptical behavior of these helical compounds in the solution state. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2022 Elektronická adresa https://doi.org/10.1002/ejoc.202001177
Počet záznamů: 1