Hydroxy-terminated poly(2,2 -substituted- 1, 3-propylene oxide) telechelics and co-telechelics bearing semifluorinated (R = -CH2OCH2(CF2)(n)CF3, n = 0, 1) and/or bromomethyl pendant groups were synthesized from the corresponding 3,3-substituted oxetanes. The new telechelics were incorporated in polyurethanes (PUs) with isophorone diisocyanate (IPDI) and 1,4-butanediol (BD) as the hard block. Surface properties were evaluated using tapping mode atomic force microscopy (TM-AFM) and dynamic contact angle (DCA) analysis. Interestingly, polyurethanes containing P(3FOx-BrOx) have higher theta(adv) and lower theta(rec) than the homo-telechelic PUs [P(3FOx) = poly(2-methyl-2-trifluoroethoxymethyl-1,3-propylene oxide; P(BrOx) = poly(2-methyl-2-bromomethyl-1,3-propylene oxide)]. For IPDI-BD(40)/P(3F0x/BrOx-1:1), theta(adv) (116 degrees) is higher and theta(rec) (32 degrees) is lower (Delta theta, 84 degrees) than any other homo- or co-telechelic polyurethane. The unusual wetting behavior for P(FOx/BrOx) polyurethanes is correlated with FOx-BrOx dyad content, and a reversible H-bonding mechanism is proposed to explain the results.