Novel nitrogen containing polymers via Reissert chemistry

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Virginia Tech

Novel A-A and A-B difunctional monomers were synthesized by utilizing Reissert compound chemistry and via the use of bis(α-aminonitrile)s. These monomers were produced in high yields with preformed heterocyclic nuclei which included benzothiazole, isoquinoline and quinoline. Acylated linear polyamine derivatives were obtained by the step growth condensation polymerization of open chain bis(Reissert compound)s with suitable dihaloalkanes; intrinsic viscosities of up to 0.48 dl/g were obtained in unoptimized runs. The constitutional repeat unit of these polymers consists of four independent structural variables and thus provides versatility for tailor made macromolecular syntheses.

Novel bis(Schiff base) monomers based on 1,4-trans-diamino cyclohexane were synthesized and these could be used either directly in the production of poly(azomethine aryl ether)s or synthesis of diamines and dicarboxylic acids containing the trans cyclohexyl moiety.

Novel aromatic diamine based bis(α-aminonitrile)s were synthesized from commercially available diamines and are currently being used in the syntheses of post-reaction modifiable co-polyamides.

A novel and unique product of rearrangement of benzothiazole Reissert compounds was isolated and characterized. It was postulated that the reaction proceeds via a bimolecular reaction between 2-cyanobenzothiazole and the’ ring opened azomethinethiophenoxide followed by an intramolecular acyl transfer and eventual reaction with methyl iodide leading to a novel benzothiazine.

A novel nucleophilic aromatic substitution reaction was discovered which involved the reaction of a masked carbonyl carbanion synthon with activated aromatic fluorides. Hitherto unknown poly(aryl ketone sulfone)s were synthesized when this chemistry was extended with the use of bis(α-aryl aminonitrile)s.

A novel quinodimethane was synthesized in quantitative yield by an intramolecular dehydrocyanation. Its structural features are unique in that one end is substituted by a donor moiety while the other end is captodative: this makes it attractive in the fields where electrical conductance and non linear optical (NLO) applications are important.