Functionalization of Poly(2-ethynylpyridinium bromide) via Copper-catalyzed Azide-alkyne Click Chemistry
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Poly(2-ethynylpyridinium bromide) is one of the conjugated polyacetylenes containing ionic pendent groups. Since poly(2-ethynylpyridinium bromide) can be prepared by the direct polymerization of 2-ethynylpyridine and propargyl bromide under mild reaction condition, several kinds of function groups have been introduced into the polymer chains. In this study, the copper-catalyzed azide-alkyne click (CuAAc) chemistry is applied as a method of introducing functional groups into poly(2-ethynylpyridinium bromide). For CuAAc reaction, we prepared poly(N-propargyl-2-ethynylpyridinium bromide) having a “clickable” propargyl side chain. By using the copper catalyzed reaction between the propargyl group of poly(N-propargyl-2-ethynylpyridinium bromide) and azide containing compounds, we demonstrate that several functional groups are successfully introduced into the side chain of the ionic conjugated polymer through post-polymerization modification.