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Synthesis of chiral molecules for understanding and revealing the expression, transfer, and amplification of chirality is beneficial to explore effective chiral medicines and high-performance chiroptical materials. Herein, we report a series of square-planar phosphorescent platinum­(II) complexes adopting a dominantly closed conformation that exhibit efficient chiroptical transfer and enhancement due to the nonclassical intramolecular C–H···O or C–H···F hydrogen bonds between bipyridyl chelating and alkynyl auxiliary ligands as well as the intermolecular π–π stacking and metal–metal interactions. The spectroscopic and theoretical calculation results demonstrate that the chirality and optic properties are regulated from the molecular level to hierarchical assemblies. Notably, a 154 times larger g abs value of the circular dichroism signals is obtained. This study provides a feasible design principle to achieve large chiropticity and control the expression and transfer of the chirality.

The development of photocontrolled assembly of smart materials with time‐dependent optical characteristics is a promising strategy to fabricate multiple optical materials for advanced information encryption. Herein, this work reports the integration of photochoromic spiropyran and square‐planar platinum(II) as a photocontrolled switching motif that endows the materials with dynamic assembly‐induced optical characteristics. Importantly, the time‐resolved multilevel optical switching processes have been achieved based on the synergism of the reversible photochoromism and fluorescence resonance energy transfer (FRET) processes through regulating the intramolecular isomerization and intermolecular self‐assembly processes. The excellent temporal multicolor features promote the photocontrolled switches as a promising candidate for time‐resolved confidential materials including multilevel displays and dynamic 4 dimension (4D) codes, with the achievement of relative encrypted data that can only be identified at a specified time. This synergistical strategy for constructing advanced materials provides an inspiring guidance for information encryption with higher security requirements.

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