Synthesis and polymerization of novel octa-substituted phthalocyanines

CHED 876

Elizabeth J.O. Atkinson and Verina F. Kranak. Department of Chemistry, Linfield College, 900 SE Baker st, McMinnville, OR 97128
Metallated octa-substituted phthalocyanines (R8MPc’s) form ordered, liquid crystalline (LC) supramolecular assemblies when the length of the attached side chains is greater than or equal to eight atoms, and the addition of an aromatic moiety to the side chains helps orient the side chains around the Pc core leading to higher degrees of order. The addition of a polymerizable group within the side chains may further order and stabilize the Pc aggregates formed upon self-assembly. Polymerization of the side chains may act as a zipper to create high molecular weight stacks of oligomers or polymers which may have semi-conductor or lithographic applications. A novel octa-substituted phthalocyanine was synthesized, where the side chains were composed of a three carbon spacer and a cinnamoyl functional group CuPc(OC3H6O2CC2H2Ph)8. The polymerization of the Pc in degassed chloroform using 254 nm UV-light was examined using UV-visible spectroscopy. An average polymerizable rate constant of 4.5X10-4mmin-1 was determined.

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