Synthesis and self-assembly of chiral Gemini-shaped hexabenzocoronene amphiphiles

Abstract Herein, we focus on constructing Gemini-shaped amphiphilic hexa- peri -hexabenzocoronene (HBC) derivatives, CHBC s and FHBC s, carrying chiral hydrophilic substituents. Compared with CHBC s, FHBC s bears four fluorine substituents at the periphery of the core. The self-assembly behaviors of the HBCs were systematically investigated by scanning electron microscopy (SEM), transmission electron microscopy (TEM) and circular dichroism (CD) spectra. CHBC s self-assembling to form a nanotubular structure under certain conditions, while FHBC s self-assembling to give non-tubular aggregates. All the ordered assemblies formed by CHBC s and FHBC s are CD-active.