The syntheses of two novel iptycene monomers, 1,4-diiodotriptycene (5) and
2,3-diiodo-4,9-dihydro-4,9-benzonaphtho[2,3,c]thiophene (10), are described
herein. These monomers were subsequently copolymerized with a number of di
ethynylphenyl monomers via a Sonogashira-Hagihara coupling to afford both r
egiodefined polymers and random terpolymers. Terpolymers derived from coupl
ing 5 and 2,5-dihexadecyloxyl,1,4-diiodobenzene with a diethynylpentiptycen
e exhibit emission spectra that are only slightly perturbed from solution t
o the solid state, suggesting that polymer association is effectively inhib
ited in condensed phases. An "all-iptycene" polymer (13) derived from the c
opolymerization of 10 with a diethynylpentiptycene monomer is also notable
in that it owes its solubility to a combination of its nonlinearity and the
presence of rigid iptycene groups rather than to flexible side chains.