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J Am Chem Soc. 2014 Sep 17;136(37):12832-5. doi: 10.1021/ja506646s. Epub 2014 Sep 8.

One-pot synthesis and AFM imaging of a triangular aramide macrocycle.

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Department of Chemistry, University of Fribourg , Chemin du Musée 9, CH-1700 Fribourg, Switzerland.


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 macrocyclization 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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