Synthesis and Properties of [60]Fullerene Derivatives Functionalized through Copper Catalyzed Huisgen Cycloaadition Reactions.

Abstract

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 [60]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. Keywords: Alkynes, azides, click chemistry, cycloaddition, fullerene, synthetic methods.