Competition between chiral solvents and chiral monomers in the helical bias of supramolecular polymers

Marcin L Ślęczkowski, Mathijs F.J. Mabesoone, Piotr Ślęczkowski, Anja R.A. Palmans (Corresponding author), E.W. Meijer (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

63 Citations (Scopus)


Solute-solvent interactions are key for the assembly and proper functioning of biomacromolecules and play important roles in many fields of organic and polymer chemistry. Despite numerous reports describing the effects of (chiral) solvents on helical conformations of (supramolecular) polymers, the combination of chiral solvents and chiral monomers is unexplored. Here we report diastereomeric differences in the supramolecular polymerization of enantiomers of chiral triphenylene-2,6,10-tricarboxamides in chiral chlorinated solvents. Competition between the preferences induced by the stereocentres of the assembled monomers and those present in the solvent molecules results in unforeseen temperature-dependent solvation effects. By combining experiments and mathematical modelling, we show that the observed differences between enantiomers originate from the combined additive entropic effects of stereocentres present in the monomer and in the solvent. Remarkably, copolymerizations show that the chiral solvent can bias the copolymer helicity and thereby overrule the helical preference of the monomers. Our results highlight the importance of cumulative solvation effects in supramolecular polymerizations.

Original languageEnglish
Pages (from-to)200-207
Number of pages8
JournalNature Chemistry
Issue number2
Early online date30 Nov 2020
Publication statusPublished - Feb 2021


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