Self-assembly of bent-core amphiphiles joining the ethylene-oxide/lithium ion tandem

•The synthesis of bent-core amphiphiles with a TEG tail and their materials containing [1/1] lithium ions are reported.•TEG-decorated bent-core molecules are versatile amphiphiles to build nanostructured soft materials.•The Li-doped materials stabilize layered bent-core liquid crystal phases such as the SmCP or HNF-like organizations.•The compounds form organogels with nonpolar solvents that provide platelets, helical fibers, and tubular morphologies.•By self-assembly, non-chiral bent core-based materials transfer conformational chirality to nanostructures. The synthesis, supramolecular self-assembly and structural characterization of a new family of tetraethylene oxide (TEG)-based bent-core compounds and their 1/1 lithium-containing complexes are reported. TEG-based bent-core amphiphiles, even joining the TEG/Li+ tandem, are suitable building-blocks to achieve supramolecular nanostructures, in some cases showing chiral features from achiral molecules either in the mesophase or in solvents. The thermal and liquid crystal behavior of these materials studied by polarizing optical microscopy and X-ray diffraction confirmed that Li-based materials stabilized polar smectic C and helical nanofilament-type mesophases, in contrast to the non-liquid crystalline pure TEG-compounds. Alternatively, both the pure amphiphiles and the lithium-doped materials self-assemble into physical gels in non-polar solvents, displaying three-dimensional networks composed of long fibers with lamellar molecular organizations as shown by transmission electron microscopy and X-ray diffraction. Interestingly, biphenyl- and azobenzene-based bent core amphiphiles aggregate in solvent into chiral nanostructured morphologies with supramolecular trends comparable to their molecular arrangement in their liquid crystalline phases.