Journal article Open Access

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

Christof Storz; Michael Badoux; Christopher M. Hauke; Tomas Solomek; Angelika Kühnle; Thomas Bally; Andreas F.M. Kilbinger

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 providedon 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.

Files (5.1 MB)
Name Size
5.1 MB Download
Views 19
Downloads 39
Data volume 197.3 MB
Unique views 18
Unique downloads 37


Cite as