Synthesis of Long Oxahelicenes by Polycyclization in a Flow Reactor
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475338" target="_blank" >RIV/61388963:_____/17:00475338 - isvavai.cz</a>
Alternative codes found
RIV/68407700:21230/17:00311607
Result on the web
<a href="http://dx.doi.org/10.1002/anie.201700341" target="_blank" >http://dx.doi.org/10.1002/anie.201700341</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.201700341" target="_blank" >10.1002/anie.201700341</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of Long Oxahelicenes by Polycyclization in a Flow Reactor
Original language description
A series of oxahelicenes composed of ortho/meta-annulated benzene/pyridine and 2H-pyran rings were synthesized on the basis of the cobalt(I)-mediated (or rhodium(I)- or nickel(0)-mediated) double, triple, or quadruple [2+2+2] cycloisomerization of branched aromatic hexa-, nona-, or dodecaynes, thus allowing the construction of 6, 9, or 12 rings in a single operation. The use of a flow reactor was found to be beneficial for the multicyclization reactions. The stereogenic centers present in some of the oligoynes steered the helical folding in such a way that the final oxa[9]-, [13]-, [17]- and [19] helicenes were obtained in both enantiomerically and diastereomerically pure form. Specifically, the oxa[19]helicenes beat the current record in the length of a helicene backbone. Single-molecule conductivity was studied by the mechanically controllable break-junction method with a pyridooxa[9]helicene.
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
<a href="/en/project/GA16-08294S" target="_blank" >GA16-08294S: Giant nonplanar aromatics: The quest for new functional materials</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Angewandte Chemie - International Edition
ISSN
1433-7851
e-ISSN
—
Volume of the periodical
56
Issue of the periodical within the volume
21
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
5839-5843
UT code for WoS article
000400755800033
EID of the result in the Scopus database
2-s2.0-85018612093