Počet záznamů: 1
Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films
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SYSNO ASEP 0490755 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Asymmetric Synthesis of Nonracemic 2-Amino[6]helicenes and Their Self-Assembly into Langmuir Films Tvůrce(i) Karras, Manfred (UOCHB-X)
Holec, Jan (UOCHB-X) RID
Bednárová, Lucie (UOCHB-X) RID, ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Schmidt, B. (DE)
Stará, Irena G. (UOCHB-X) RID, ORCID
Starý, Ivo (UOCHB-X) RID, ORCIDZdroj.dok. Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 83, č. 10 (2018), s. 5523-5538Poč.str. 16 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova aminohelicene ; asymmetric synthesis ; self-assembly Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA16-08294S GA ČR - Grantová agentura ČR Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000432900800019 EID SCOPUS 85046399326 DOI 10.1021/acs.joc.8b00538 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2019
Počet záznamů: 1