We designed glutamide-derived amphiphilic Schiff bases containing three different aldehyde moieties for the fabrication of circularly polarized luminescence (CPL) emitting materials. Upon self-assembly in acetonitrile, Schiff bases featuring 4-(dimethylamino)-2-hydroxylbenzaldehyde and 1-hydroxy-2-naphthaldehyde groups form supramolecular gels with twist and fiber structures, respectively, whereas Schiff bases featuring 2-hydroxy-l-naphthaldehyde groups form precipitation with flake structures. Although emission and circular dichroism signals can be detected from the supra molecular gels formed by amphiphilic Schiff bases, none of them exhibits a circularly polarized luminescence (CPL). Although Mg2+, Zn2+, and Al3+ can significantly enhance the fluorescence of the Schiff bases, interestingly, only Al3+ ion is able to turn on the CPL emission. This study on the one hand provides a simple method for the fabrication of CPL-emitting supramolecular materials and on the other hand offers a novel way for the sensing of aluminum ion with supramolecular materials.