The synthesis of four side-chain liquid crystalline polymethacrylates containing either 4-alkanyloxy-4’-flourodiphenyldiactylenes or 4-alkanyloxy-3’,4’-difluorodiphenyldiacetylenes side groups is presented. The phase behavior of both monomeric and polymeric liquid crystals was characterized by differential scanning calorimetry and optical polarizing microscopy. All synthesized polymethacrylates present nematic mesomorphism. The glass transition temperature of the obtained polymers decreases as the spacer length increases. The mesomorphic behavior of the prepared polymers depends very much on the degree of substitution of the mesogenic side groups on the polymer backbones.