Iptycene-Containing Poly(aryleneethynylene)s

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 diethynylphenyl monomers via a Sonogashira−Hagihara coupling to afford both r...

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Bibliographic Details
Published in:Macromolecules 2000-05, Vol.33 (11), p.4069-4073
Main Authors: Williams, V. E, Swager, T. M
Format: Article
Language:English
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Summary: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 diethynylphenyl monomers via a Sonogashira−Hagihara coupling to afford both regiodefined polymers and random terpolymers. Terpolymers derived from coupling 5 and 2,5-dihexadecyloxy1,1,4-diiodobenzene with a diethynylpentiptycene exhibit emission spectra that are only slightly perturbed from solution to the solid state, suggesting that polymer association is effectively inhibited in condensed phases. An “all-iptycene” polymer (13) derived from the copolymerization 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.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma991938j