Reversible Manipulation of Supramolecular Chirality using Host–Guest Dynamics between β‐Cyclodextrin and Alkyl Amines

Host–guest interactions are widely employed in constructing responsive materials, although less is known to manipulate the chiral property of materials using such host–guest dynamics. With the supramolecular self‐assembly based on β‐cyclodextrin (β‐CD) and alkyl amines (CH3(CH2)n‐1NH2), we report that faster host–guest dynamics induces a dipole located above the cavity of β‐CD, whereas slower dynamics create in‐cavity dipole. These two scenarios correspond to negative and positive chiral signals, respectively. Considering that a larger fraction of amines facilitates faster exchange between the threaded and unthreaded amines, the chiral signal for the right‐handed helical ribbons can be manipulated simply by alternatively increasing the fraction of amines and β‐CD. Excitingly, enzyme responsive supramolecular chirality is obtained as a result of shifting the molar ratio by enzyme triggered hydrolysis of β‐CD. We expect that this strategy may open up an area of rationally designed chiral supramolecular materials based on host–guest chemistry. The host‐to‐guest molar fraction can affect the location of the dipole of the alkyl amine guests in the cavity of β‐cyclodextrin(β‐CD), inducing positive or negative chiral signals. Thus, the supramolecular chirality can be simply manipulated by alternatively increasing the fraction of amines and β‐CD, or by enzyme‐triggered hydrolysis of β‐CD, which reduces the molar fraction of β‐CD.