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

Abstract

Abstract Herein, we focus on constructing Gemini-shaped amphiphilic hexa-peri-hexabenzocoronene (HBC) derivatives, CHBCs and FHBCs, carrying chiral hydrophilic substituents. Compared with CHBCs, FHBCs 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. CHBCs self-assembling to form a nanotubular structure under certain conditions, while FHBCs self-assembling to give non-tubular aggregates. All the ordered assemblies formed by CHBCs and FHBCs are CD-active.