1,4-Bis[(3’-fluoro-4’-n-alkoxyphenyl)ethynyl]toluenes mimic the thermotropic behavior of poly{5-[[[2’,5’-bis[(4’-n-alkoxybenzoyl)oxy]benzyl]oxy]carbonyl]bicyclo[2.2.1]hept-2-ene}s better than 1,4-bis[(3’-fluoro-4’-n-alkoxyphenyl)ethynyl] do. Polymers with approximately 50 repeat units and narrow polydispersity (pdi = 1.08-1.23) were prepared by ring-opening metathesis polymerization of 5-{[[2’,5’-bis[2-(3’-fluoro-4’-n-alkoxyphenyl)ethynyl]benzyl]oxy]carbonyl}bicyclo[2.2.1]hept-2-enes in THF using Mo(CHCMe2Ph)(N-2,6-(Pr2Ph)-Pr-i)((OBu)-Bu-t)(2) as the initiator. All of the polymers exhibit an enantiotropic nematic mesophase in addition to the glass transition, and those with n = 3-12 slowly organize into a crystalline or s(E) phase that occurs over an extremely narrow temperature range. Whereas 1,4-bis[(3’-fluoro-4’-n-alkoxyphenyl)ethynyl]benzenes exhibit a k-s(E)-s(C)-n-i phase sequence when n = 6-12, all of the 1,4-bis[(3’-fluoro-4’-n-alkoxyphenyl)ethynyl]toluenes exhibit a nematic mesophase, and those with n = 9-12 also exhibit either a monotropic s(C) mesophase or an enantiotropic s(C) mesophase over a very narrow temperature range.