55 research outputs found
One-pot synthesis and AFM imaging of a triangular aramide macrocycle
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
Chiral Induction in Phenanthroline-Derived Oligoamide Foldamers: An Acid- and Base-Controllable Switch in Helical Molecular Strands
N-Phenylphthalimide-Type Cyclooxygenase (COX) Inhibitors Derived from Thalidomide: Substituent Effects on Subtype Selectivity
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