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

• Autoři: STORZ C.; BADOUX M.; HAUKE CM.; ŠOLOMEK Tomáš; KUHNLE A.; BALLY Thomas Walter; KILBINGER AFM.
• Rok publikování: 2014
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: Journal of the American Chemical Society
• Fakulta / Pracoviště MU: Přírodovědecká fakulta
• Doi: http://dx.doi.org/10.1021/ja506646s
• Obor: Vliv životního prostředí na zdraví
• Klíčová slova: SHAPE-PERSISTENT MACROCYCLES; P-AMINOBENZOIC ACID; BUILDING-BLOCKS; SUPRAMOLECULAR CHEMISTRY; DIRECTED SYNTHESIS; ORGANIC NANOTUBES; OLIGOMERS; EFFICIENT; TEMPLATE; ARYLENE
• Popis: 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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