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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F11%3A00358625" target="_blank" >RIV/61388963:_____/11:00358625 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201001110" target="_blank" >http://dx.doi.org/10.1002/ejoc.201001110</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201001110" target="_blank" >10.1002/ejoc.201001110</a>

Result language
angličtina
Original language name
Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates
Original language description
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).
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year
2011
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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