One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle

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Authors

STORZ C. BADOUX M. HAUKE CM. ŠOLOMEK Tomáš KUHNLE A. BALLY Thomas Walter KILBINGER AFM.

Year of publication 2014
Type Article in Periodical
Magazine / Source Journal of the American Chemical Society
MU Faculty or unit

Faculty of Science

Citation
Doi http://dx.doi.org/10.1021/ja506646s
Field Environment influence on health
Keywords SHAPE-PERSISTENT MACROCYCLES; P-AMINOBENZOIC ACID; BUILDING-BLOCKS; SUPRAMOLECULAR CHEMISTRY; DIRECTED SYNTHESIS; ORGANIC NANOTUBES; OLIGOMERS; EFFICIENT; TEMPLATE; ARYLENE
Description Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocydization to occur. Linear polymers are formed exclusively in the absence of this Li-chelating group. A model that explains the lack of formation of other cyclic congeners and the demand for an N-(o-alkoxybenzyl) protecting group is provided on the basis of DFT calculations. High-resolution AFM imaging of the prepared molecular triangles on a calcite(10.4) surface shows individual molecules arranged in groups of four due to strong surface templating effects and hydrogen bonding between the molecular triangles.
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