Pushing the limits of chiral amplification in supramolecular polymers

N,N',N''-trialkylated-benzene-1,3,5-tricarboxamides (BTAs) self-assemble via strong, threefold αhelix 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 apolar 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 BTAbased supramolecular polymers by introducing H/D isotope chirality into the alkyl side chains of BTAs at the a-position. We determine the relative stabilities of the leftand 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 to a cooperative self-assembly process, which is highly sensitive to the applied solvent.