期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 5, 页码 853-860出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001110
关键词
Arenes; Alkynes; Cyclotrimerisation; Nanostructures; Scanning probe microscopy
资金
- European Commission [FP6-015847]
- Czech Science Foundation [P207/10/2207]
- Ministry of Education, Youth and Sports of the Czech Republic [LC512]
- Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [Z4 055 0506]
Heptahelicene-2-carboxylic acid was effectively synthesised from suitably functionalised naphthalene building blocks. Methoxy-substituted 1,1'-ethyne-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).
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