A route toward multifunctional polyurethanes using triple click reactions

Abstract

The aliphatic polyurethane with pendant alkyne, perfluorophenyl, and anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracene, alkyne, and perfluorophenyl functional-diols with hexamethylenediisocyanate in the presence of dibutyltindilaurate (DBTL) in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-(anthracene-co-alkyne-co-perfluorophenyl) (Mn,GPC = 15,400 g/mol, Mw/Mn= 1.37, relative to PS standards) was sequentially clicked with benzyl azide, octylamine, and 4-(2-hydroxyethyl)−10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (adduct alcohol) via copper-catalyzed azide-alkyne cycloaddition, active ester substitution and Diels–Alder reactions, respectively, to finally yield PU-(hydroxyl-co-benzyltriazole-co-octylamine). The PUs were characterized using 1H NMR, GPC, and DSC. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015