Synthesis of High Performance Aromatic Polymers via Nucleophilic Nitro Displacement Reaction

Abstract

Nucleophilic displacement reaction of activated aromatic nitro groups with various nucleophiles is a useful and versatile method for the synthesis of aromatic compounds such as ethers, thioethers and other functionalized intermediates and polymers. Various strong electron withdrawing groups can activate aromatic nitro groups. Effective activating groups include cyano, nitro, sulfone and carbonyl groups such as ester, ketone, anhydride, imide, etc. The reaction of activated nitro compounds with bisphenols and bisthiophenols yields bisethers and bisthioethers from which various aromatic polymers containing ether and sulfide groups can be derived. In many cases, nitro displacement reactions are essentially quantitative so that high molecular weight polymers are directly prepared by the displacement reaction of difunctional nitro compounds with bisphenols or bisthiophenols. Another type of unique nitro displacement occurs in the presence of catalytic amount of a nucleophile at higher temperatures resulting de-nitro coupling of two molecules of nitro compound to form substituted diarylethers.