Imidazole-substituted ROMP polymers: Post-modification of poly(norbornenediester) derivatives with aminolysis reactions

Abstract

In this study, ring-opening metathesis polymerization (ROMP) polymers bearing imidazole and morpholine functionalities were synthesized using an efficient and inexpensive post-modification procedure. First, dimethyl-5-norbornene-2,3-dicarboxylate was polymerized (Mn: 130kDa, Ð: 1.23) in the presence of Grubbs third-generation catalysts through ROMP reactions. Second, these ROMP polymers were modified using octylamine, 1-(3-aminopropyl)imidazole, and 1-(3-aminopropyl)morpholine in the presence of catalytic amounts of tin(II)hexanoate; Sn(Oct)2, titanium(IV)isopropoxide; Ti(O-i-Pr)4; and 1,5,7-triazabicyclo[4.4.0]dec-5-ene. Modified polymers were characterized by 1H, 13C NMR, FT-IR, differential scanning calorimetry, thermogravimetric analysis, and gel permeation chromatography. Quantitative conversions were achieved using 1-(3-aminopropyl)imidazole as a modification agent in the presence of 10% Sn(Oct)2.