Topochemical polymerization of pyridyl muconates via supramolecular rational design

Topochemical polymerization of pyridyl muconates via supramolecular rational design

Crystalline polymers

Supramolecular chemistry

Whitfield, Wesley Alan

2005

Dinkelmeyer, Brian

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Lattice-controlled reactivity of monomers in the solid state is a method of forming polymers with stereoregularity and high molecular weight. We formed a supramolecular system using a cocrystallization strategy utilizing hydrogen bonding interactions of bis-1, 6-(methylpyridyl)-(E, E)-muconate guests and dicarboxylic acid oxalamide hosts. Oxalamides form well known one-dimensional networks via the amide-amide hydrogen bonding synthon. Pyridyl-carboxylic acid interactions are another proliferate hydrogen bonding synthon. Thus, dipyridyl muconates should form two-dimensional networks via interaction with carboxylic acid-terminated oxalamides self-assembled in a 1-D network via the amide-amide synthon (See Figure 11 for illustration of cocrystallization strategy). The hydrogen bonded assembly of the oxalamides should allow formation of a crystal lattice capable of undergoing topochemical photopolymerization. Topochemical reactivity was observed for the 2-methylpyridyl muconate guest which underwent 1,4- photopolymerization along the diolefin backbone of the pyridyl muconate guest molecules. Cocrystals of the other hosts and guests did not polymerize and these will be studied in the future.

2014-07-22

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