The construction of chiroptical materials with controllable chirality is of special importance in biology and chemistry. Although tunable chirality can be realized in various systems, it remains a fundamental challenge to realize multimodulated chiral inversion. Herein, we report that chiral alanine derivative and fluorescent cyanostilbene derivative co-assemble to prepare supramolecular chiral systems, where twist nanofibers with totally inverted supramolecular chirality and circularly polarized luminescence are obtained through stoichiometric modulation. The supramolecular handedness can be inverted by means of altering the cooling rate and incorporating metal ions. The mechanism study reveals that the synergistic effect among hydrogen bonds, coordination interactions, and π–π stacking interactions contributes to the chirality inversion. This work establishes an effective strategy to precisely modulate supramolecular chirality in multiple ways, which shows great potential in developing smart chiroptical materials capable of achieving complex functionalities.

Regulation of self-assembly morphology is an effective strategy to obtain advanced functional materials with expected properties. However, achieving remarkable morphological transformation by light irradiation is still a challenge. Herein, three simple spiropyran derivatives (SP1, SP2, and SP3) are constructed, achieving different degrees of morphological transformation from nanospheres to hollow tadpole-like structures (SP3), tubular structures (SP2), and microsheets (SP1) after ultraviolet light irradiation. Interestingly, the hollow tadpole-like structures (SP3) can further extend to Y-shaped or T-shaped tubular morphology. In the process, SP1, SP2, and SP3 can be isomerized from a closed-ring form (hydrophobicity) to an open-ring form (hydrophilicity) in different degrees, interacting differently with methanol solvent molecules. The formation of hollow structures or microsheets along with the isomerization of spiropyran derivatives contributes to the adjustment of the hydrophilicity of the interface. Therefore, SP1, SP2, and SP3 with photoregulated morphological transformation show promising applications in tunable interface materials.