Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00539547" target="_blank" >RIV/61388963:_____/21:00539547 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/ejoc.202001177" target="_blank" >https://doi.org/10.1002/ejoc.202001177</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.202001177" target="_blank" >10.1002/ejoc.202001177</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis, Chiral Resolution, and Optical Properties of 2,18-Dihydoxy-5,10,15-trioxa[9]helicene
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
1099-0690
Volume of the periodical
2021
Issue of the periodical within the volume
1
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
146-150
UT code for WoS article
000596696600001
EID of the result in the Scopus database
2-s2.0-85097318063