Syntheses, via precursor polymers, of polyethers containing 9,10-diacetoxyanthracene units or 9,10-anthraquinone units: chemical reactions of some of these polymers

Abstract

Reaction of the bisphenol that is formally the Diels–Alder adduct of 2,6-dihydroxy-9,10-diacetoxyanthracene and dimethyl maleate with bis-acid chlorides and base in phase transfer catalysed reactions gives precursor polyethers. On heating the latter in a vacuum at 250–280°C retro-Diels–Alder reactions occur, with the loss of dimethyl maleate, to afford polymers containing 9,10-diacetoxyanthracene residues. Treating the precursor polyethers with sodium ethoxide in N,N-dimethylformamide converts them into soluble polymers containing units which are the disodium salts of the hydroanthraquinone. Aerial oxidation of these solutions gives polymers containing anthra-9,10-quinone (AQ) residues. Selected examples of the polymers containing 9,10-diacetoxyanthracene residues were similarly converted into the soluble polymers containing salt residues and thence into the corresponding AQ-containing polymers. Thus, we have shown that AQ-containing polymers can be prepared successfully by this novel type of precursor polymer approach.