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

Storz C, Badoux M, Hauke CM, Solomek T, Kühnle A, Bally T, Kilbinger AFM (2014)
Journal of the American Chemical Society 136(37): 12832-12835.

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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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Storz C, Badoux M, Hauke CM, et al. One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle. Journal of the American Chemical Society. 2014;136(37):12832-12835.
Storz, C., Badoux, M., Hauke, C. M., Solomek, T., Kühnle, A., Bally, T., & Kilbinger, A. F. M. (2014). One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle. Journal of the American Chemical Society, 136(37), 12832-12835. doi:10.1021/ja506646s
Storz, C., Badoux, M., Hauke, C. M., Solomek, T., Kühnle, A., Bally, T., and Kilbinger, A. F. M. (2014). One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle. Journal of the American Chemical Society 136, 12832-12835.
Storz, C., et al., 2014. One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle. Journal of the American Chemical Society, 136(37), p 12832-12835.
C. Storz, et al., “One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle”, Journal of the American Chemical Society, vol. 136, 2014, pp. 12832-12835.
Storz, C., Badoux, M., Hauke, C.M., Solomek, T., Kühnle, A., Bally, T., Kilbinger, A.F.M.: One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle. Journal of the American Chemical Society. 136, 12832-12835 (2014).
Storz, Christof, Badoux, Michael, Hauke, Christopher M., Solomek, Tomas, Kühnle, Angelika, Bally, Thomas, and Kilbinger, Andreas F. M. “One-Pot Synthesis and AFM Imaging of a Triangular Aramide Macrocycle”. Journal of the American Chemical Society 136.37 (2014): 12832-12835.
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PMID: 25178114
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