The syntheses of two novel iptycene monomers, 1,4-diiodotriptycene (I) and 2,3-diiodo-4,9-dihydro-4,9-benzonaphtho[2,3,c]thiophene (II), are described herein. These monomers were subsequently copolymd. with a no. of diethynylphenyl monomers via a Sonogashira-Hagihara coupling to afford both regiodefined polymers and random terpolymers. Terpolymers derived from coupling I and 2,5-dihexadecyloxy1,1,4-diiodobenzene with a diethynylpentiptycene exhibit emission spectra that are only slightly perturbed from soln. to the solid state, suggesting that polymer assocn. is effectively inhibited in condensed phases. An äll-iptycene\" polymer derived from the copolymn. of II with a diethynylpentiptycene monomer is also notable in that it owes its soly. to a combination of its nonlinearity and the presence of rigid iptycene groups rather than to flexible side chains. [on SciFinder(R)]