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

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• 作者：Christof Storz ; Michael Badoux ; Christopher M. Hauke ; Tom谩拧 艩olomek ; Angelika K眉hnle ; Thomas Bally ; Andreas F. M. Kilbinger
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：September 17, 2014
• 年：2014
• 卷：136
• 期：37
• 页码：12832-12835
• 全文大小：387K
• ISSN：1520-5126

文摘

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.