AbstractPoly(arylene ether oxadiazole) telechelics with fluorine and hydroxyl end groups were synthesized by nucleophilic substitution polymerizations of 2,5‐bis(4‐fluorophenyl)‐1,3,4‐oxadiazole monomer with bishydroxy compounds containing C(CH3)2, C(CF3)2 and SO2 groups. Fluorotelechelics were obtained with about 3 repeating units (molecular weight about 2 000 g · mol−1) using a rather excess (100 mol‐%) of bis(fluorophenyl) oxadiazole compound. On the other hand, hydroxytelechelics were synthesized with about 9 repeating units (molecular weight about 5 000 g · mol−1) using a small excess of bishydroxy compound (monomer molar ratio of 0.93). Sulfonated poly(arylene ether oxadiazole) hydroxytelechelics were also synthesized using sulfonated and unsulfonated bishydroxy compounds. All sulfonated hydroxytelechelics were partially water soluble, even when only 40 mol‐% of sulfonated monomers was used. The number of repeating units of hydroxytelechelics increased up to 12 (molecular weight about 9 000 g · mol−1) using sulfonated monomers, probably because of the higher reactivity of sulfonated phenoxide. The molecular weights estimated by 1H NMR were in agreement to the results obtained by SEC. The telechelics can be used as precursor for the synthesis of block copolymer.Structure of the hydroxytelechelics.magnified imageStructure of the hydroxytelechelics.