There is a great demand for self-assembled carbon nanomaterials because of their importance in optoelectronics, biomaterials, and so forth. Herein, we report a novel type of self-assembled, nanoscale, crystalline vesicle from nonplanar π-conjugated nanocycles. We designed four different structural [8]cycloparaphenylenes ([8]CPPs) molecules and demonstrated that these nonplanar π-conjugated CPP nanocycles could self-assemble into multilamellar, crystalline vesicles in tetrahydrofuran (THF)/H 2 O mixed solvent. The critical driving force for the assembly of nanoscale CPP vesicles is crystallization and π-π interaction of nonplanar, nanocyclic molecules. The size of CPP vesicles could be regulated by changing water content, temperature, and concentration in solution. Our data demonstrate that these π-conjugated nanocycle-based vesicles show a remarkable ability to enter cells in an energy-or temperature-independent manner and kill cancer cells. When the side groups of the CPP molecule were changed, the CPP vesicles showed a large difference in the cytotoxicity, and two CPP vesicles could effectively kill cancer cells as well as first-class antitumor agents.
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