9-(3-Acetoxy-1-methylpropyl)-8,13-difluoro-1,4-dimethyltriptycene and 9-(1-methyl-2-propenyl)-8,13-difluoro-1,4-dimethyl- and 1,2,3,4-tetrachloro-triptycenes were prepared. Their barriers to internal rotation around the C(9)–C(alkyl) bonds were measured by the classical kinetics. The barrier was affected a little by the substituent, being ca. 25–26 kcal mol-1. Rotamer distributions in these compounds and possible causes for these indifferent barriers to rotation are discussed.