Synthesis, electrochemistry, and photophysical properties of pyrazolino[60]fullerene-1,8-naphthalimide fluorescent derivatives

A series of pyrazolino[60]fullerene-1,8-naphthalimide (Pz[60]-NI) fluorescent derivatives were synthesized in one pot by a [3+2] dipolar cycloaddition between C60 and functionalized hydrazones in good yield. In contrast with 4-aziridino[60]fullerene-1,8-naphtalimide dyads, Pz[60]-NI derivatives present stronger fluorescence intensity. Electrochemical study revealed that Pz[60]-NI presents better electron accepting character than the parent C60. The natural bond orbital of the dyads were calculated using density functional theory method and found that the sp3 nitrogen atom in the pyrazoline ring plays a key role in the charge transfer process.