Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00490755" target="_blank" >RIV/61388963:_____/18:00490755 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/acs.joc.8b00538" target="_blank" >http://dx.doi.org/10.1021/acs.joc.8b00538</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.8b00538" target="_blank" >10.1021/acs.joc.8b00538</a>

Result language
angličtina
Original language name
Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films
Original language description
Alternative ways of preparing nonracemic 2-amino[6]helicene derivatives were explored. The enantioselective [2 + 2 + 2] cycloisomerization of a nonchiral triyne under Ni(cod)(2)/(R)-QUINAP catalysis delivered the enantioenriched (+)-(P)-2-aminodibenzo[6]helicene derivative in 67% ee. An ultimate “point-to-helical” chirality transfer was observed in the cyclization of enantiopure triynes mediated by Ni(CO)(2)(PPh3)(2) affording (-)-(M)- or (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amine in >99% ee as well as its benzoderivative in >99% ee. The latter mode of stereocontrol was inefficient for a 2-aminobenzo[6]helicene congener with an embedded five-membered ring. The rac-, (-)-(M)-, and (+)-(P)-7,8-bis(p-tolyl)hexahelicen-2-amines formed Langmuir monolayers at the air water interface featuring practically identical surface pressure vs mean molecular area isotherms. The corresponding Langmuir-Blodgett films on quartz or silicon substrates were characterized by UV vis/ECD spectroscopy and AFM microscopy, respectively.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

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)

Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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