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{5-[[[2‘,5‘-Bis[(4‘‘-(n-(perfluoroalkyl)alkoxy)benzoyl)oxy]benzyl]oxy]carbonyl]bicyclo[2.2.1]hept-2-ene}s were polymerized by ring-opening metathesis polymerization in THF at 40 °C using Mo(CHCMe₂Ph)(N-2,6-ⁱPr₂Ph)(O^tBu)₂ as the initiator. 2,5-Bis[(4‘-(n-(perfluoroalkyl)alkoxy)benzoyl)oxy]toluenes mimic both the phases formed by the poly{5-[[[2‘,5‘-bis[(4‘‘-(n-(perfluoroalkyl)alkoxy)benzoyl)oxy]benzyl]oxy]carbonyl]bicyclo[2.2.1]hept-2-ene}s and the general temperatures of their transitions, and are therefore excellent models of the polymers. In contrast to their hydrocarbon analogs which exhibit only nematic mesophases, all of the polymers and their low molar mass model compounds exhibit smectic C and smectic A mesophases. In both cases, all of the transition temperatures decrease with increasing hydrocarbon length and increase with increasing fluorocarbon length.