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Synthesis and NMR Spectroscopic Study of the Self-Aggregation of 2-Substituted Benzene-1,3,5-tricarboxyamides

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2015
Author Christian Invernizzi, Claudio Dalvit, Helen Stoeckli-Evans, Reinhard Neier,
Project The hydrogenation of calix[4]pyrroles leading to the novel ligand system calix[4]pyrrolidine: Their properties and their application
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Original article (peer-reviewed)

Journal European Journal of Organic Chemistry
Volume (Issue) 1015(23)
Page(s) 5115 - 5127
Title of proceedings European Journal of Organic Chemistry


The self-assembly of N,N’,N’’-trialkylbenzene-1,3,5-tricarboxyamides (BTAs) 1 or of “crowded” BTAs 11 and 12 lead to supramolecular columnar-stacked structures with attractive material properties. The introduction of three alkoxy groups is reported to reinforce the self-assembly process. The influence of a single substituent introduced on the aromatic core of BTA significantly affects the self-assembly process. The aggregation process of 2-substituted BTAs in the bulk and in solution, as studied by DSC, POM, X-ray diffraction and 1H NMR experiments, is impaired by H-bond accepting substituents and strengthened by non-H-bonding substituents.