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
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- English
- Classification
- Chemistry
- License
- License undefined
- Identifiers
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- RERO DOC 233083
- DOI 10.1021/ja506646s
- Persistent URL
- https://folia.unifr.ch/unifr/documents/304006
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