Self-assembly of bistriazole BDT based bolaamphiphiles into SmA phase and helical organogels

Bistriazole benzo[1,2-b:4,3-b′]dithiophene (BDT) contained bolaamphiphiles have been synthesized via Sonogashira coupling and click reactions as key steps. For such compounds, the central bent bistriazole BDT core, the flexible methylene spacer led the rodlike core together with the terminal diol groups to twist to be U-shaped polar region. Micro-segregation of U-shaped polar region from the lipophilic chains generated a SmA phase. Furthermore, these compounds can act as super organogelators to gel different kinds of solvents with the lowest critical gelation concentration (CGC) of 0.2 mg/ml. Gel morphologies with scarcely reported nanostructures including nanofibers, nanobelts, nanodisks, nanotrumpets and nanotubes were firstly observed in bolaamphiphilic self-assembly system. [Display omitted] •Bolaamphiphiles based on bistriazole BDT core have been synthesized.•They displayed only SmA phase due to the U shaped polar region.•They can act as super organogelators to form gels with exotic helical nanostructures.