Substituent group induced fluorescence emission transformation and supramolecular chirality inversion in glutamide based amphiphile assemblies

•Both the amphiphiles form assemblies and show obvious CD signals.•The cyano moiety can induce the fluorescent emission transformation.•The existence of cyano moiety lead to the supramolecular chirality inversion in DMSO/H2O co-solvents. To modulate both the emission and the chirality in assembly system is important but challenging. Here, we design and synthesize two glutamide based amphiphiles bearing cyanostilbene or stilbene moieties. Both the amphiphiles can self-assemble in DMSO/H2O mixed solvent. The existence of cyano group not only induces the fluorescent emission transformation but also leads to supramolecular chirality inversion. Density functional theory and molecular dynamic simulation are conducted and the results reveal that the cyano group has influence on both the charge distribution and the stacking mode. We believe our work will bring some insights into the modulation of supramolecular chirality by precise control of molecular structure. [Display omitted]