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Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates
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SYSNO ASEP 0358625 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates Author(s) Rybáček, Jiří (UOCHB-X) RID, ORCID
Huerta-Angeles, Gloria (UOCHB-X)
Kollárovič, Adrian (UOCHB-X)
Stará, Irena G. (UOCHB-X) RID, ORCID
Starý, Ivo (UOCHB-X) RID, ORCID
Rahe, P. (DE)
Nimmrich, M. (DE)
Kühnle, A. (DE)Number of authors 8 Source Title European Journal of Organic Chemistry - ISSN 1434-193X
-, č. 5 (2011), s. 853-860Number of pages 8 s. Language eng - English Country DE - Germany Keywords arenes ; alkynes ; cyclotrimerisation Subject RIV CC - Organic Chemistry R&D Projects GAP207/10/2207 GA ČR - Czech Science Foundation (CSF) LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000287163400004 DOI 10.1002/ejoc.201001110 Annotation Heptahelicene-2-carboxylic acid was effectively synthesised from suitably functionalised naphthalene building blocks. Methoxy-substituted 1,1'thyne-1,2-diylbis(2-but-3-yn-1-ylnaphthalene) was cyclised in the presence of CpCo(CO)2/PPh3 to 2-methoxy-7,8,11,12-tetrahydroheptahelicene, which was converted into heptahelicen-2-yl trifluoromethanesulfonate. This reactive intermediate underwent Pd(OAc)2/dppp-catalysed methoxycarbonylation reaction to provide, after hydrolysis, heptahelicene-2-carboxylic acid. The racemate was resolved into enantiomers by semipreparative HPLC on a chiral column. The helicity of (+)-(P)-heptahelicene-2-carboxylic acid was assigned by correlating its CD spectrum to that of the known (+)-(P)-heptahelicene. Racemic heptahelicene-2-carboxylic acid was deposited on calcite (10-14) to undergo self-assembly into nanowire-like aggregates as demonstrated by noncontact atomic force microscopy (NC-AFM). Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2012
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