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This work describes a novel technique to prepare a family of polymers which contain a polyquinoneimine backbone. The polymerization utilized a condensation reaction which yielded novel substituted polyanilines. The polymer generating reaction, formation of the imine, was optimized to a quantitative yield via a model compound study. The model quinoneimine was prepared from anthraquinone and two equivalents aniline in the presence of excess of titanium tetrachloride and 1,4-diazabicyclo[2.2.2]octane. The X-ray crystal structure of the model compound from anthraquinone had indicated that the ring system is not planar due to steric hindrance between the peri-hydrogen of anthraquinone and the ortho-hydrogen of the N-phenyl ring. The X-ray crystal structure of the model compound prepared from 4,8-dehydrobenzo-[1,2-b:4,5-b']dithiophene-4,8-dione reveals the quinone moiety to be planar. This indicates that the incorporation of a benzoquinone moiety with two fused thiophene rings in the model compound relieved the steric hindrance observed in the anthraquinone model compound. The model compound synthetic strategy was used to prepare polyquinoneimines from either of the above mentioned quinones and aromatic diamines. The polyquinoneimines were prepared in high yields with molecular weights up to 20,000. The polymers are red powders which are soluble in common organic solvents such as tetrahydrofuran, chloroform and chlorobenzene and form red transparent films. In contrast, polyanilines are typically black insoluble and intractible polymers. Characterization of the polymers prepared from either 4,4'-methylenedianiline or 4,4'-thiodianiline and anthraquinone revealed that 5-20% of the product is a novel low molecular weight macrocyclic quinoneimine.

Block copolymers were made containing peptides coupled to a hydrophobic regions that could be cleaved to obtain a hydrophilic region, similar to globular proteins. These polymers were synthesized by anionic polymerization of t-butyl acrylate followed by coupling with polypeptides. Anionic polymerization allowed control of molecular weight, polydispersity as well as end groups of the polymer. The polymer was terminated with a carboxylic acid or a primary amine, the desired end groups needed to couple this polymer to peptides by conventional peptide coupling reactions. Upon hydrolysis of the esters, the resulting hydrophilic-hydrophobic polymer may be used to act as specific channels through lipid membranes, to increase the solubility of peptides in hydrophilic and hydrophobic solvents or to modify particle growth of inorganic salts.

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