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Abstract
Chiral photoswitchable cages offer a versatile platform for light-controlled modulation of cavity size and conformation—critical features for enantioselective recognition and catalysis. We report the synthesis of a BINOL-derived chiral dialdehyde that forms a macrocycle and a cage via imine condensation with aliphatic bis and trisamines, respectively. All three systems exhibit reversible azobenzene E↔Z isomerisation under 370/456 nm irradiation. Notably, macrocyclization and cage formation enhance photoisomerisation efficiency and improve the thermal stability of the Z-isomer. The cage shows pronounced light-induced cavity modulation, accompanied by significant CD spectral shifts, supported by DFT analysis. These results highlight the promise of such architectures as responsive chiral hosts with tunable optical and structural features.
Supplementary materials
Title
From Macrocycle to Cage: Structural Effects on Photo-Switching and Chiroptical Properties
Description
Chiral photoswitchable cages offer a versatile platform for light-controlled modulation of cavity size and conformation—critical features for enantioselective recognition and catalysis. We report the synthesis of a BINOL-derived chiral dialdehyde that forms a macrocycle and a cage via imine condensation with aliphatic bis and trisamines, respectively. All three systems exhibit reversible azobenzene E↔Z isomerisation under 370/456 nm irradiation. Notably, macrocyclization and cage formation enhance photoisomerisation efficiency and improve the thermal stability of the Z-isomer. The cage shows pronounced light-induced cavity modulation, accompanied by significant CD spectral shifts, supported by DFT analysis. These results highlight the promise of such architectures as responsive chiral hosts with tunable optical and structural features.
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