Synthesis and Properties of Poly[2-ethynyl-N-(p-hydroxyphenylethyl) pyridinium bromide] and Poly [2-ethynyl-N-(p-hydroxyphenylethyl) pyridinium tetraphenylborate]

A new hydroxyl group-containing conjugated ionic polymer, poly[2-ethynyl-N-(p-hydroxyphenylethyl)pyridinium bromide], was synthesized by the activated polymerization of 2-ethynylpyridine with p-(2-bromoethyl) phenol without any additional initiator or catalyst. The polymerization proceeded well to give a moderate yield (65%) of polymer at a reaction temparature of 90$^{\circ}C$. Another polymer, poly[2-ethynyl-N-(p-hydroxyphenylethyl)pyridinium tetraphenylborate], was readily prepared by the ion-exchange reaction of poly[2-ethynyl-N-(p-hydroxyphenylethyl)pyridinium bromide] with sodium tetraphenylborate. These polymers were completely soluble in organic solvents such as DMF, DMSO, and acetone, but insoluble in water and ether. Instrumental analyses, such as NMR, IR, and UV-Vis spectroscopies, indicated that the new materials have conjugated polymer backbone systems with the designed substituents and counter anions. X-Ray diffraction analyses of the polymers indicated that they were mostly amorphous.