QUINODIMETHANE POLYMERS.

Abstract

Monomers and polymers containing the quinodimethane unit were synthesized. The infrared, nuclear magnetic resonance (NMR) and ultraviolet spectra of these materials were also reported. Oxidation of the enolate dianoion of α, α'-di(carbomethoxy)-α, α'-diphenylquinodimethane (DMPQH₂) with iodine gave 7,8-di(carbomethoxy)-7,8-diphenylguinodimethane (DMPQ) in greater than 50% yield. This compound had a reduction potential of -0.85V (Ag/AgCl reference) but would not form charge transfer complexes with electron donors. Attempted polymerization reactions of DMPQ were also discussed. A series of donor - acceptor substituted quinodimethanes was synthesized and a discussion of their electronic properties was included. Condensation copolyesterification of two of these materials was performed. Polymers with inherent viscosities ranging from 0.11 dL/g to 0.45 dL/g were obtained. The polymers were soluble at room temperature in hexafluoroisopropanol (HFIP) and a 1 : 1 solution of phenol/chlorobenzene. The polymers were also soluble at elevated temperatures in dipolar aprotic solvents.