Synthesis and Electrochemistry of Novel Dumbbell-Shaped Bis-pyrazolino[60]fullerene Derivatives Formed Using Microwave Radiation

Mohammad H BinSabt; Hamad M Al-Matar; Alan L Balch; Mona A Shalaby

doi:10.1021/acsomega.1c02245

Synthesis and Electrochemistry of Novel Dumbbell-Shaped Bis-pyrazolino[60]fullerene Derivatives Formed Using Microwave Radiation

ACS Omega. 2021 Jul 27;6(31):20321-20330. doi: 10.1021/acsomega.1c02245. eCollection 2021 Aug 10.

Authors

Mohammad H BinSabt¹, Hamad M Al-Matar¹, Alan L Balch², Mona A Shalaby¹

Affiliations

¹ Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait.
² Department of Chemistry, University of California at Davis, One Shields Avenue, Davis, California 95616, United States.

Abstract

The design of covalently linked [60]fullerene dimers has gained increased attention, as the linked electron donors or acceptors are in close proximity to the surface of the C₆₀, providing a valuable approach to novel molecular electronic devices. Herein, new compounds involving C₆₀ dumbbells covalently connected by the π-conjugated system from azobenzene and diaryl ether linkers were synthesized following the bifunctional cycloaddition reactions to C₆₀ using microwave radiation. The structural identity of the fullerene dimers has been determined using spectroscopic techniques including Fourier transform infrared (FT-IR), matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF), and NMR spectroscopy, and the photophysical and the electrochemical properties for the new dumbbells have been examined using UV-vis spectroscopy, fluorescence spectroscopy, cyclic voltammetry, and square wave voltammetry. Both new dimers show electronic interaction with the fullerene cage and higher electron affinity than the pristine C₆₀.