0000000000374680

AUTHOR

Jiří Rybáček

showing 3 related works from this author

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

2010

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…

chemistry.chemical_classificationStereochemistryCarboxylic acidOrganic ChemistryReactive intermediateArenes530High-performance liquid chromatographyNanostructureschemistry.chemical_compoundHydrolysisScanning probechemistryAlkynesPolymer chemistryCyclotrimerisationmicroscopySelf-assemblyPhysical and Theoretical ChemistryEnantiomerTrifluoromethanesulfonateNaphthaleneEuropean Journal of Organic Chemistry
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Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates (Eur. J. Org. Chem. 5/2011)

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.

chemistry.chemical_classificationCrystallographyChemistryStereochemistryCarboxylic acidOrganic ChemistryNanowireCover (algebra)Self-assemblyPhysical and Theoretical ChemistryEuropean Journal of Organic Chemistry
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Molecular Self-Assembly of Enantiopure Heptahelicene-2-Carboxylic Acid on Calcite (1014)

2012

Chirality can have a decisive influence on the molecular structure formation upon self-assembly on surfaces. In this paper, we study the structures formed by enantiopure (M)-heptahelicene-2-carboxylic acid ((M)-[7]HCA) on the calcite (10 (1) over bar4) cleavage plane under ultrahigh vacuum conditions. Previous noncontact atomic force microscopy studies have revealed that the racemic mixture of (M)-[7]HCA and (P)-[7]FICA (1:1) self-assembles into well-defined molecular double rows that are oriented along the calcite [01 (1) over bar0] direction. Here, we investigate the enantiopure (M)[7]HCA compound, resulting in distinctly different molecular structures upon deposition onto calcite (10 (1)…

chemistry.chemical_classificationCalciteStereochemistryCarboxylic acid530Surfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsCrystallographychemistry.chemical_compoundGeneral EnergyEnantiopure drugchemistryMoleculeRacemic mixtureMolecular self-assemblyPhysical and Theoretical ChemistryEnantiomerChirality (chemistry)
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