Počet záznamů: 1

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

  1. 1.
    0358625 - UOCHB-X 2012 RIV DE eng J - Článek v odborném periodiku
    Rybáček, Jiří - Huerta-Angeles, Gloria - Kollárovič, Adrian - Stará, Irena G. - Starý, Ivo - 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. -, č. 5 (2011), s. 853-860 ISSN 1434-193X
    Grant CEP: GA ČR(CZ) GAP207/10/2207; GA MŠk LC512
    Grant ostatní: FP6-European Commission(XE) 015847
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: arenes * alkynes * cyclotrimerisation
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 3.329, rok: 2011

    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).
    Trvalý link: http://hdl.handle.net/11104/0196595