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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
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.
Erscheinungsjahr
2014
Zeitschriftentitel
Journal of the American Chemical Society
Band
136
Ausgabe
37
Seite(n)
12832-12835
ISSN
0002-7863
Page URI
https://pub.uni-bielefeld.de/record/2913791

Zitieren

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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