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By dealing CrCl₃∙3THF with the corresponding ligands (<b>L1</b>–<b>L5</b>), an array of fluoro-substituted chromium (III) chlorides (<b>Cr1</b>–<b>Cr5</b>) bearing 2-[1-(2,4-dibenzhydryl-6-fluoro- phenylimino)ethyl]-6-[1-(arylimino)ethyl]pyridine (aryl = 2,6-Me₂Ph <b>Cr1</b>, 2,6-Et₂Ph <b>Cr2</b>, 2,6-iPr₂Ph <b>Cr3</b>, 2,4,6-Me₃Ph <b>Cr4</b>, 2,6-Et₂-4-MePh <b>Cr5</b>) was synthesized in good yield and validated via Fourier Transform Infrared (FT-IR) spectroscopy and elemental analysis. Besides the routine characterizations, the single-crystal X-ray diffraction study revealed the solid-state structures of complexes <b>Cr2</b> and <b>Cr4</b> as the distorted-octahedral geometry around the chromium center. Activated by either methylaluminoxane (MAO) or modified methylaluminoxane (MMAO), all the chromium catalysts exhibited high activities toward ethylene polymerization with the MMAO-promoted polymerizations far more productive than with MAO (20.14 × 10⁶ g (PE) mol⁻¹ (Cr) h⁻¹ vs. 10.03 × 10⁶ g (PE) mol⁻¹ (Cr) h⁻¹). In both cases, the resultant polyethylenes were found as highly linear polyethylene waxes with low molecular weights around 1–2 kg mol⁻¹ and narrow molecular weight distribution (MWD range: 1.68–2.25). In general, both the catalytic performance of the <i>ortho</i>-fluorinated chromium complexes and polymer properties have been the subject of a detailed investigation and proved to be highly dependent on the polymerization reaction parameters (including cocatalyst type and amount, reaction temperature, ethylene pressure and run time).