Synthesis and Properties of Fullerene Derivatives Functionalized through Copper Catalyzed Huisgen Cycloaadition Reactions.
José L. Segura, Marta Castelaín and Horacio Salavagione
Affiliation: Departamento de Química Orgánica. Facultad de Química. Universidad Complutense de Madrid. E-28040, Madrid-Spain.
Keywords: Alkynes, azides, click chemistry, cycloaddition, fullerene, synthetic methods.
Fullerenes are fascinating carbon molecules that attract an increasing attention due to their interesting properties and possibilities
of application. For these applications fullerenes need to be connected to the macroscopic world via their exterior. Hence, the modification
of fullerenes to acquire the desired exterior functionality is of major importance to utilize them effectively as bulk materials in
practical applications. In last years, the copper-catalyzed Huisgen’s 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC)
has been revealed as an efficient tool for the preparation of a variety of fullerene derivatives with interesting applications. In this review
we will brush up the variety of fullerene building blocks developed to be used in CuAAC reactions and we will critically examine the variety
of reaction conditions that have been used to perform the CuAAC in connection with the nature of the moieties attached to the
fullerene core. Moreover, the properties and applications of fullerene derivatives obtained via the CuAAC “click” methodology will
be reviewed including their use as mimics of the photosynthetic antenna-reaction center, their biological activity, their use as thermoresponsive
water-soluble polymers and their role in the preparation of supramolecular fullerene motifs.
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