Non-stoichiometric effect in the superacid-catalyzed polyhydroxyalkylation of biphenyl and 1-propyl isatin

Abstract

An experimental study on the superacid-catalyzed polyhydroxyalkylation of biphenyl (A2 monomer) and 1-propyl isatin (B2 monomer) at non-stoichiometric conditions is presented. The produced high-performance polymers were characterized by gel permeation chromatography matrix-assisted laser-desorption/ionization-time-of-flight (MALDI-TOF), nuclear magnetic resonance and diffusion-ordered spectroscopy (DOSY). High molecular weights (Mw > 150,000 Da) and ultra-high molecular weights (Mw ∼ 900,000 Da) are obtained when B2 is used in excess, which agrees with the behavior observed at non-stoichiometric conditions for other superacid catalyzed polyhydroxyalkylations, contrary to the case when A2 is used in excess, where a reduction in molecular weight is obtained, as reported in a previous study from our group. A, B, and M types of linear polymer molecules, as well as C-type cycles, were observed from the MALDI-TOF data.