ZWITTERIONIC POLYMERIZATION OF 4-[(4-HYDROXY-1-NAPHTHYL)THIO]BUTYL]QUINUCLIDINIUM HYDROXIDE INNER SALT

The zwitterion, 4-[(4-hydroxy-1-naphthyl)thio]butyl]quinuclidinium hyd roxide inner salt, was synthesized from tetrahydro-1-(4-hydroxy-1-naph thyl)thiophenium hydrochloride and quinuclidine and characterized by N MR and IR spectroscopy. Polymerization of the zwitterion was studied o ver the temperature range 175-225 degrees C. The polymer was identifie d as diylethyleneoxy-1,4-naphthylenethiotetramethylene) based on NMR a nd IR spectroscopy. The polymer was found to contain 3-butenylthio and 4-hydroxy-1-naphthyl end groups. Based on the signal area of the olef inic end group, the polymer (M) over bar(n) varied between 8500 and 13 ,000. The highest molecular weight was achieved at the lowest temperat ure, indicating that termination became more favored at higher tempera ture. A mechanism is proposed to describe the polymerization. (C) 1996 John Wiley & Sons, Inc.