AIE‐Switching and Enantioselective Reactivity at Jammed Liquid‐Liquid Interface

Abstract

The jammed liquid‐liquid interface offers an elegant approach to achieve non‐equilibrium shapes of liquids. The interfacial jamming subsequently brings about formation of 2D “solid‐like” assembly. In this work, biphasic reaction between a perylenediimide based luminogen benzoperylenediimide monoanhydride (Bp(Im)₂MA) and diamines are demonstrated that rendered amide bond formation and in turn amide nanoconjugates across the oil‐water interface. Amide nanoconjugates formed with different diamines showed diamine alkyl chain length dependent varied interfacial properties and sizes. Jamming of the interface is judiciously utilized to induce aggregation of amide nanoconjugates which successfully established macroscopic Aggregation Induced Emission‐switching (AIE‐switching) behavior. Further, the versatility of this approach is extended to analyze the reactivity of chiral amino acids. The reaction between the Bp(Im)₂MA luminogen and chiral amino acids exhibits macroscopic enantioselectivity at jammed interface via diverse surface coverage of the amino acids‐based amide nanoconjugates. The formation of discrete nanoscopic amide interfacial assembly for each of the L‐ and D‐ amino acids isomers is corroborated with Atomic Force Microscopy (AFM) images. This study extends a fascinating pathway to aid in understanding and fabrication of structurally diverse jammed interfaces and aggregation of organic molecules across an oil‐water interface.