TY  - JOUR
AB  - 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).
DA  - 2011
DO  - 10.1002/ejoc.201001110
KW  - Arenes
KW  - Alkynes
KW  - Cyclotrimerisation
KW  - Nanostructures
KW  - Scanning probe
KW  - microscopy
LA  - eng
IS  - 5
M2  - 853
PY  - 2011
SN  - 1434-193X
SP  - 853-860
T2  - European Journal of Organic Chemistry
TI  - Racemic and Optically Pure Heptahelicene-2-carboxylic Acid: Its Synthesis and Self-Assembly into Nanowire-Like Aggregates
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-29138258
Y2  - 2024-11-21T16:33:54
ER  -