Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates

Rybacek J, Huerta-Angeles G, Kollarovic A, Stara IG, Stary I, Rahe P, Nimmrich M, Kühnle A (2011)
European Journal of Organic Chemistry (5): 853-860.

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Abstract
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 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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Rybacek J, Huerta-Angeles G, Kollarovic A, et al. Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates. European Journal of Organic Chemistry. 2011;(5):853-860.
Rybacek, J., Huerta-Angeles, G., Kollarovic, A., Stara, I. G., Stary, I., Rahe, P., Nimmrich, M., et al. (2011). Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates. European Journal of Organic Chemistry(5), 853-860. doi:10.1002/ejoc.201001110
Rybacek, J., Huerta-Angeles, G., Kollarovic, A., Stara, I. G., Stary, I., Rahe, P., Nimmrich, M., and Kühnle, A. (2011). Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates. European Journal of Organic Chemistry, 853-860.
Rybacek, J., et al., 2011. Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates. European Journal of Organic Chemistry, (5), p 853-860.
J. Rybacek, et al., “Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates”, European Journal of Organic Chemistry, 2011, pp. 853-860.
Rybacek, J., Huerta-Angeles, G., Kollarovic, A., Stara, I.G., Stary, I., Rahe, P., Nimmrich, M., Kühnle, A.: Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates. European Journal of Organic Chemistry. 853-860 (2011).
Rybacek, Jiri, Huerta-Angeles, Gloria, Kollarovic, Adrian, Stara, Irena G., Stary, Ivo, Rahe, Philipp, Nimmrich, Markus, and Kühnle, Angelika. “Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates”. European Journal of Organic Chemistry 5 (2011): 853-860.
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