Synergistic chiroptical and energy transfer mediated by hydrogen bonding in a Binary System based on a histidine-functionalized Cyanostilbene

• C4CNHis forms double-helix showing CD & fluorescence. • H-bond (His-carboxylate) locks dual CT/ET synergy mechanism. • Strategy for tunable chiroptical materials established. Achieving synergistic control of chiral transfer (CT) and energy transfer (ET) in co-assembled systems presents a fundamental challenge for designing advanced chiroptical materials. We address this by synthesizing a histidine-headed cyanostilbene amphiphile ( C4CNHis ) and constructing a multicomponent co-assembly platform. Single-crystal X-ray diffraction reveals a double-helical superstructure for C4CNHis, which exhibits distinct circular dichroism (CD) signals and blue fluorescence in DMF/H₂O mixed solvents. Crucially, co-assembly with a carboxyl-functionalized triarylamine acceptor enables simultaneous ET and CT, whereas a non-carboxylated acceptor facilitates only ET without CT. Fourier transform infrared (FTIR) spectroscopy and molecular dynamics simulations demonstrate that hydrogen bonding between the imidazolium group of histidine and the carboxylate group underpins this synergistic transfer. This work establishes a hydrogen-bond-locked mechanism for dual CT/ET synergy, providing a rational design strategy for tunable chiroptical materials.