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This paper reports a comprehensive study on the synthesis and self-assembly of two model series of molecular shape amphiphiles, namely, hydrophilic [60]fullerene (AC₆₀) tethered with one or two polystyrene (PS) chain(s) at one junction point (PS_n–AC₆₀ and 2PS_n–AC₆₀). The synthesis highlighted the regiospecific multiaddition reaction for C₆₀ surface functionalization and the Huisgen 1,3-dipolar cycloaddition between alkyne functionalized C₆₀ and azide functionalized polymer to give rise to shape amphiphiles with precisely defined surface chemistry and molecular topology. When 1,4-dioxane/DMF mixture was used as the common solvent and water as the selective solvent, these shape amphiphiles exhibited versatile self-assembled micellar morphologies which can be tuned by changing various parameters, such as molecular topology, polymer tail length, and initial molecular concentration, as revealed …