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Synthesis and NMR Spectroscopic Study of the Self‐Aggregation of 2‐Substituted Benzene‐1,3,5‐tricarboxamides
Author(s) -
Invernizzi Christian,
Dalvit Claudio,
StoeckliEvans Helen,
Neier Reinhard
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500506
Subject(s) - chemistry , substituent , hydrogen bond , supramolecular chemistry , self assembly , ene reaction , crystallography , proton nmr , ring (chemistry) , alkoxy group , stereochemistry , alkyl , molecule , organic chemistry , crystal structure
The self‐assembly of N , N′ , N″ ‐trialkylbenzene‐1,3,5‐tricarboxamides (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 onto 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 1 H NMR experiments, is impaired by hydrogen‐bond‐accepting substituents but strengthened by non‐hydrogen‐bond‐accepting substituents.