The horseradish peroxidase- (HRP-) catalyzed polyrecombination of N-(4-hydroxyphenyl)-2-furamide (2) and 4-hydroxyphenylmaleimide (1) is described. The resulting copolymer was used to build crosslinked materials via Diels-Alder and cycloaddition reactions. We followed the enzymatic copolymerization process of an equimolar mixture of 1 and 2 using high pressure liquid chromatography (HPLC), size-exclusion chromatography (SEC) and by matrix assisted laser desorption/ionization-time of flight mass spectroscopy (MALDI-TOF MS) analysis and found that the polymerization of 2, which has a significant higher highest occupied molecular orbital (HOMO) energy, proceeds much faster. The HOMO energies of 1 and 2 were calculated using a differential Fourier transform (DFT) method. Furthermore, we tested copolymers consisting of the monomer units 4-hydoxybenzaldehyde-methylnitrone (3) and N-methacryloyl-11-aminoundecanoyl-4-hydroxyanilide (4) on their ability to form networks via 1,3-dipolaric cycloaddition reactions upon heating. The crosslinking of all copolymers was proven by Fourier transform infrared (FT-IR) spectroscopy.
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Reihmann et al. (2001) studied this question.