0000000000374678
AUTHOR
Adrian Kollárovič
Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates
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)/PPh(3) 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 spectr…
Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates (Eur. J. Org. Chem. 5/2011)
The cover picture shows heptahelicene-2-carboxylic acid, whose synthesis and self-assembly are central to the article. The background features Prague's riverbank, which is intermixed with the nanowire-like aggregates of heptahelicene-2-carboxylic acid. The alignment of the swans makes the link between self-assembly and the Prague view. Details are discussed in the article by I. G. Stara, I. Starý, A. Kuhnle et al. on p. 853 ff. Background photo by M. Bělohradský.