Thermally Activated Stereoinversion in Benzotrithiophene-Based Supramolecular Polymers with Water as the Effector.

ABSTRACT: We report the synthesis of the chiral benzotrithiophene (BTT) derivative 1, which self-assembles into helical supramolecular polymers. The C₃ symmetry of BTT 1 enables a unique temperature-dependent stereomutation process in which water acts as a key effector. Circular dichroism measurements reveal that a higher water content induces a double stereomutation, ultimately restoring the original helicity. In contrast, reducing the water content leads to a single, stable stereomutation, which duration depends on the amount of water in solution. To elucidate the stereomutation mechanism, we conducted a multi-level computational study, identifying two main conformations for the monomeric species that lead to diastereomeric helices with different preferred handedness, thus resulting in

SUBMITTER: Lopez-Gandul L 

PROVIDER: S-EPMC12723459 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature