The widespread use of graphene as a next-generation material in various applications requires developing an environmentally friendly and efficient method for fabricating functionalized graphene. Chemically, graphene can be used as an electron donor or attractor. Here, graphite was successfully exfoliated, and an in situ Diels-Alder reaction (D-A) was carried out to fabricate functionalized graphene with sole functional groups via mechanochemical ball milling. The reactivities of graphene acting as a diene or a dienophile were investigated. Few-layer (≤2 layers) graphene specimens were obtained by wet ball milling, heating in a nitrogen atmosphere, and solvent ultrasonic treatment. The ball-milling method was more effective than heating in a nitrogen atmosphere, and the [2 + 4] D-A of graphene was more dominant than the [4 + 2] D-A in the ball-milling process. The surface tension of functionalized graphene decreased, which provided a theoretical basis for the dispersion and exfoliation of graphite in a suitable solvent. Functionalized graphene still had a high electrical conductivity, which has far-reaching significance for functionalized graphene to be applied in electronic semiconductors and related applications. Meanwhile, functionalized graphene was applied to polymer composite fibers, the tensile strength and the Young's modulus could reach 780 MPa and 19 GPa. The volume resistivity was two orders of magnitude lower than that of pure fiber. Thus, the use of ball milling to efficiently exfoliate and in situ functionalize graphite will help to develop a strategy that can be widely used to manufacture nanomaterials for various application fields.
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