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Novel Conjugated Polymer Containing Aromatic Ring and Selenium in Backbone. Kinetics of the Addition Reaction as the Model for Addition Polymerization

The addition reaction mechanism of benzeneselenol to ethynylbenzene was studied as a model for the addition polymerization (so called polyaddition) of 1,4-benzenediselenol to 1,4-diethynylbenzene. The addition reaction occurred without an appreciable side reaction in the presence of AIBN and an adduct of the anti-Markownikoff’s structure (⌬–Se–CH = CH–⌬) was quantitatively obtained. The addition reaction is very similar to the addition polymerization of 1,4-benzenediselenol to 1,4-diethynylbenzene from the point of the geometrical structure of the polymer chain. A kinetic study showed that a rate-determining step of the addition reaction was the addition step of the benzeneseleno radical to ethynylbenzene. The results were compared with those of the addition reaction of benzenethiol to ethynylbenzene. By the competitive addition reaction, ethynylbenzene had 80 times higher reactivity than styrene toward benzeneselenol at 60°C in benzene.