Adaptive Chirality of an Achiral Cucurbit[8]uril-Based Supramolecular Organic Framework for Chirality Induction in Water

Chiral framework materials have been developed for many applications including chiral recognition, chiral separation, asymmetric catalysis, and chiroptical materials. Herein, we report that an achiral cucurbit[8]uril-based supramolecular organic framework (SOF-1) with the dynamic rotational conformation of tetraphenylethene units can exhibit adaptive chirality to produce M-SOF-1 or P-SOF-1 with mirror-image circular dichroism (CD) with g(abs)approximate to +/- 10(-4) and circularly polarized luminescence (CPL) with g(lum)approximate to +/- 10(-4) induced by L-/D-phenylalanine in water, respectively. The chirality induction in CD (g(abs)approximate to-10(-4)) and CPL (g(lum)approximate to-10(-4)) of P-SOF-1 from achiral SOF-1 can be presented by using a small amount of adenosine-5 '-triphosphate disodium (ATP) or adenosine-5 '-diphosphate disodium (ADP) (only 0.4 equiv) in water. Furthermore, the adaptive chirality of SOF-1 can be used to determine dipeptide sequences (e.g., Phe-Ala and Ala-Phe) and distinguish polypeptides/proteins (e.g., somatostatin and human insulin) with characteristic CD spectra. Therefore, achiral SOF-1 as an ideal chiroptical platform with adaptive chirality may be applied to determine the enantiopurity of amino acids (e.g., L-/D-phenylalanine), develop aqueous CPL materials, and distinguish biological chiral macromolecules (e.g., peptides/proteins) via chirality induction in water.

Automated summary

Achiral supramolecular organic framework (SOF-1) can exhibit adaptive chirality induced by specific compounds in water, leading to mirror-image circular dichroism and circularly polarized luminescence. This adaptive chirality can be utilized for determining the enantiopurity of amino acids and distinguishing biological chiral macromolecules.