N,N',N "-tr(alkylated-benzene-1,3,5-tricatboxamides (BTAs) self-assemble via strong, threefold u-helix type intermolecular hydrogen bonding into well-defined, helical, one dimensional columnar aggregates. The introduction of a stereogenic centre into the alkyl side chains of BTAs gives rise to strong Cotton effects in dilute apoiar solutions Indicating the preference for one helical conformation over the other. Here, we summarise our research on the influence of the position of the stereogenic centre on the aggregate stability and the degree of amplification of chirality in BTAs. In addition, we disclose our results on creating a preferred helical sense in BTA-based supramolecular polymers by introducing H/D isotope chirality info the alkyl side chains of BTAs at the K-posifion. We determine the relative stabilities of the leff-and right-handed helical conformers formed by these deuterated molecules by performing a conformational analysis in different alkane solvents. Our findings show that the subtle difference between the stabilities of the two conformers leads fo a cooperative self-assembly process, which is highly sensitive to the applied solvent.
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