TY  - JOUR
AB  - 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.
DA  - 2014
DO  - 10.1021/ja506646s
LA  - eng
IS  - 37
M2  - 12832
PY  - 2014
SN  - 0002-7863
SP  - 12832-12835
T2  - Journal of the American Chemical Society
TI  - One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-29137912
Y2  - 2024-11-22T05:24:08
ER  -