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As a conventional strategy to modulate the structure and properties of inorganic single crystals, hydration/solvation is rarely found to function in pure organic single crystal. Herein, we report chalcone single crystals with CHCl3-dependent emission color and jumping behavior. Two crystals: a pure crystal phase (1) with green-yellow emission and a CHCl3-containing co-crystal phase (1•2CHCl3) with orange-red emission were constructed by fine-controlling the crystallization conditions. The special halogen bond network in the crystal packing structure effectively narrows the bandgap and thereby redshift the emission of 1•2CHCl3. 1•2CHCl3 would revert to 1 together with emission color change when losing CHCl3. These findings are similar to the effect of H2O in hydrated inorganic crystals. Notably, owing to a special pre-organized “molecular pair” structure for [2 + 2] cycloaddition, the pure crystal phase 1 exhibits violently photo-induced jumping phenomenon, indicating large potentials in intelligent devices. This work would overturn the previous perception that the structurally simple solvent molecules without conjugation cannot greatly affect the structure and properties of pure organic single crystals and provide a new strategy to construct multi-colored organic fluorescent crystals.

CHCl3-Dependent Emission Color and Jumping Behavior of Cyclic Chalcone Single Crystals: The Halogen Bond Network Effect