A strong interface between the single-walled carbon nanotubes (SWNTs) and polymer matrix is necessary to achieve enhanced mechanical properties of composites. In this work a series of sidewall-functionalized SWNTs have been investigated in order to evaluate the effect of functionalization on SWNT aspect ratio and composite interfacial chemistry and their role on mechanical properties of a medium density polyethylene (MDPE) matrix. Fluorinated nanotubes (F-SWNTs) were used as precursors for subsequent sidewall functionalization with long chain alkyl groups to produce an F-SWNT- C₁₁H₂₃ derivative. The latter was refluorinated to yield a new perfluorinated derivative, F-SWNT- C₁₁F_xH_y. The functionalized SWNTs as well as the pristine SWNTs were integrated into an MDPE matrix at a 1 wt% loading. The nanotubes and composite materials were characterized with FTIR, Raman spectroscopy, NMR, XPS, AFM, SEM, TGA, DSC and tensile tests. When incorporated into polyethylene, the new perfluorinated derivative, F-SWNT- C₁₁F_xH_y, yielded the highest tensile strength value among all nanotube/MDPE composite samples, showing a 52% enhancement in comparison with the neat MDPE. The 1 wt% SWNT/MDPE composite contained nanotubes with a larger aspect ratio but, due to a lack of interfacial chemistry, it resulted in less improvement in mechanical properties compared to the composites made with the fluorinated SWNT derivatives.