Amphiphilic Corannulene Derivatives: Synthetic Access and Development of a Structure/Property Relationship in Thermoresponsive Buckybowl Amphiphiles

Eight new derivatives of corannulene have been synthesized, characterized, and examined for their water solubility and thermally triggered assembly behavior. To achieve this, the hydrophobic corannulene core was attached to the hydrophilic polyethylene glycol arm(s). Here, the substitution pattern as well as the arm length was varied systematically. Furthermore, the hydrophobic/hydrophilic ratio was adjusted by incorporating a phenyl ring at the junction point of the two moieties. A properties study revealed that a proper balance among the number, length, and chemical nature of the arm was required to ensure water solubility and thermoresponsive character. Remarkably, the lower critical solution temperature could be modulated within the range of 30-50 °C simply through adjusting the molecular structure of the assembling building block. This work, therefore, demonstrates synthetic feasibility of a wide range of amphiphilic corannulene derivatives and opportunity for modulation of their thermoresponsive behavior.