Michael Heinenberg, B. Menges, S. Mittler
Apr 23, 2002
Citations
0
Influential Citations
18
Citations
Journal
Macromolecules
Abstract
Various vinylbenzaldehydes were prepared using the Heck reaction: 4-vinylbenzaldehyde (14), 3-vinylbenzaldehyde (15), 2-vinylbenzaldehyde (18a), 2-hydroxy-4-vinylbenzaldehyde (16) and 4-[(4-vinylbenzyl)oxy]benzaldehyde (6). The four monomers (6, 14, 15, 16) were polymerized using AIBN as initiator at 70 °C for 24 h to yield the corresponding homopolymers (7, 19, 23, 25) and a copolymer (20) with styrene. The molecular weights are about 10 000. The polymer analogous condensation of the aldehyde groups with an excess of N-isopropylhydroxylamine (8) at room temperature produces polymeric nitrons (9, 21, 22, 24, 26) in almost quantitative yields. All nitron functions were irradiated, and the intramolecular cyclization of the nitrons to the corresponding oxaziridines was examined. Waveguide mode spectroscopy of poly(4-vinylbenzaldehyde-N-isopropylnitron) (21) shows that the changes in film thickness are low but the changes in refractive indices are significant after irradiation. Oxaziridine 10 has high therma...