One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle
| Authors | |
|---|---|
| Year of publication | 2014 |
| Type | Article in Periodical |
| Magazine / Source | Journal of the American Chemical Society |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1021/ja506646s |
| Field | Environment influence on health |
| Keywords | SHAPE-PERSISTENT MACROCYCLES; P-AMINOBENZOIC ACID; BUILDING-BLOCKS; SUPRAMOLECULAR CHEMISTRY; DIRECTED SYNTHESIS; ORGANIC NANOTUBES; OLIGOMERS; EFFICIENT; TEMPLATE; ARYLENE |
| Description | 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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