Chiral induction by natural biomolecules can reveal the indispensable role of chiral structures in life and can be used to develop the chirality-sensing biomolecular recognition. Here, we present the synthesis and characterization of an achiral supramolecular organic framework (SOF-1) constructed from cucurbit[8]uril (CB[8]) and hexaphenylbenzene (HPB) derivative (1) in water. Due to the propeller-like rotational chiral conformation of HPB units and the specific recognition properties of CB[8], SOF-1 demonstrates chiral adaptive induction in water when interacting with the N-terminal Trp-/Phe-containing dipeptides including L-TrpX and L-PheX (X is an amino acid residue), respectively, exhibiting contrasting circular dichroism (CD) and circularly polarized luminescence (CPL) spectra. Consequently, SOF-1 has been developed as a supramolecular host and chiroptical sensor capable of recognizing and distinguishing the sequence-opposite Trp-/Phe-containing dipeptide pairs including L-TrpX/L-XTrp and L-PheX/L-XPhe based on the sequence-selective CD responses.
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