Synthesis and Stereochemical Behavior of Dioxa[6]helicene Derivatives
Result description
We constructed a helically chiral dioxa[6]helicene by assembling simple phenol building blocks by a combination of two simple reactions involving oxidative cross-coupling followed by dehydrative cyclization. X-ray analysis and density functional calculations (DFT) revealed that the compound dioxa[6]helicene has a helical structure that undergoes helical inversion rapidly at room temperature. We were able to detect the presence of resolvable helical isomers of (−)-menthyloxycarbonyl derivative of dioxa[6]helicene by recording 1H NMR spectra below 0 °C. The investigations of photo physical properties by cyclic voltammetry, UV/Vis- and fluorescence properties with the aid of time-dependent DFT calculations were undertaken.
Keywords
density functional calculationsdynamic resolutionhelicenessingle-crystal analysisvariable temperature NMR spectroscopy
The result's identifiers
Result code in IS VaVaI
Result on the web
DOI - Digital Object Identifier
Alternative languages
Result language
angličtina
Original language name
Synthesis and Stereochemical Behavior of Dioxa[6]helicene Derivatives
Original language description
We constructed a helically chiral dioxa[6]helicene by assembling simple phenol building blocks by a combination of two simple reactions involving oxidative cross-coupling followed by dehydrative cyclization. X-ray analysis and density functional calculations (DFT) revealed that the compound dioxa[6]helicene has a helical structure that undergoes helical inversion rapidly at room temperature. We were able to detect the presence of resolvable helical isomers of (−)-menthyloxycarbonyl derivative of dioxa[6]helicene by recording 1H NMR spectra below 0 °C. The investigations of photo physical properties by cyclic voltammetry, UV/Vis- and fluorescence properties with the aid of time-dependent DFT calculations were undertaken.
Czech name
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Czech description
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Classification
Type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
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
ChemistrySelect
ISSN
2365-6549
e-ISSN
2365-6549
Volume of the periodical
6
Issue of the periodical within the volume
17
Country of publishing house
DE - GERMANY
Number of pages
6
Pages from-to
4035-4040
UT code for WoS article
000656879800001
EID of the result in the Scopus database
2-s2.0-85107551059
Result type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
OECD FORD
Organic chemistry
Year of implementation
2021