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One-pot synthesis and AFM imaging of a triangular aramide macrocycle

  • Storz, Christof Department of Chemistry, University of Fribourg, Switzerland
  • Badoux, Michael Department of Chemistry, University of Fribourg, Switzerland
  • Hauke, Christopher M. Institut für Physikalische Chemie, Johannes Gutenberg Universität Mainz, Germany - Graduate School of Excellence Materials Science in Mainz, Germany
  • Šolomek, Tomáš Department of Chemistry, University of Fribourg, Switzerland - RECETOX and Department of Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic
  • Kühnle, Angelika Institut für Physikalische Chemie, Johannes Gutenberg Universität Mainz, Germany
  • Bally, Thomas Department of Chemistry, University of Fribourg, Switzerland
  • Kilbinger, Andreas F. M. Department of Chemistry, University of Fribourg, Switzerland
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    17.09.2014
Published in:
  • Journal of the American Chemical Society. - 2014, vol. 136, no. 37, p. 12832–12835
English 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.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/304006
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