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Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene
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SYSNO ASEP 0539547 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene Author(s) Shyam Sundar, Mothuku (UOCHB-X) ORCID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Bednárová, Lucie (UOCHB-X) RID, ORCID
Muller, G. (US)Source Title European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2021, č. 1 (2021), s. 146-150Number of pages 5 s. Language eng - English Country DE - Germany Keywords chiral HPLC ; circular dichroism ; helicenes ; heterohelicenes ; enantiomers ; optical properties OECD category Organic chemistry Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000596696600001 EID SCOPUS 85097318063 DOI 10.1002/ejoc.202001177 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2022 Electronic address https://doi.org/10.1002/ejoc.202001177
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