Poly(DMI-1, 2-Diazinediylethene-l, 2-Diols)

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Abstract
Oligomers of 2 to 9 units having a diazinediylethene-1, 2-diol repeating unit have been prepared by a cyanide ion-catalyzed self-condensation of pyridazine-3, 6-, pyrazine-2, 5-, or pyrimidine-4, 6-dialdehyde. These are the first known representatives of a class of conjugated polymeric enediol materials derivable specifically from these three structurally related diazine dialdehydes. The oligomers, isolated as their potassium salts, are soluble in acid and base with an isoelectric point at pH 6.5. In base, they give dark red-brown solutions whose color, attributable to their semidione ion radical form, is rapidly discharged by oxygen (air) or by the addition of ferric ion, which gives an immediate precipitation of the black chelate. Of several possible methods evaluated for the preparation of the free dialdehydes, only that involving ozonization of the distyryldiazines was found to be of preparative value.