The synthesis and "living" cationic polymerization of 3-fluoro-4’-(11-vinyloxyundecanyloxy)-4-biphenylyl (2R,3S)-2-fluoro-3-methylpentanoate (12-11) and 3-fluoro-4’-(8-vinyloxyoctyloxy) -4-biphenylyl (2R,3S)-2-fluoro-3-methylpentanoate (12-8) are presented. Poly(12-11)s and poly(12-8)s with degrees of polymerization from 4.0 to 16.5 and polydispersities less than or equal to 1.13 have been synthesized and characterized by differential scanning calorimetry (DSC) and thermal optical polarized microscopy. Over the entire range of molecular weights poly(12-11)s and poly(12-8)s exhibit an enantiotropic S-A and an unidentified S-X phase. In addition, regardless of its molecular weight, poly(12-8) exhibits a S-c* phase in between the S-A and S-X phases. Poly(12-11) and poly(12-8) show lower transition temperatures and broader temperature ranges of all their mesophases as compared to the corresponding polymers without a fluorine atom on the biphenyl group. The role of the connecting group between the biphenyl and chiral group of the mesogenic unit on the phase behavior of these polymers is also discussed. Copolymers of 12-8 with (2R,3S)-2-fluoro-3-methylpentyl 4’-(11-vinyloxyundecanyloxy)biphenyl-4-carboxylate (13-11) {i.e., poly- [(12-8)-co-(13-11)] (X/Y), where X/Y represents the molar ratio of monomer 12-8 to monomer 13-11} with DP of ca. 11 and polydispersities lower than 1.23 were also synthesized and characterized. Their S-A and S-C* mesophases exhibit continuous dependences of composition and this supports the assignment of the mesophases exhibited by poly(12-8).