96915-62-7Relevant academic research and scientific papers
Polymeric nitrons. 2. Synthesis, irradiation and waveguide mode spectroscopy of polymeric nitrons derived from polymeric benzaldehydes and N-isopropylhydroxylamine
Heinenberg, Michael,Menges, Bernhard,Mittler, Silvia,Ritter, Helmut
, p. 3448 - 3455 (2007/10/03)
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 thermal stability with respect to ring opening. No structural change was detected after irradiation of the hydrexyphenyl-modified polynitron (26). A low molecular weight model compound (2-hydroxybenzaldehyde-N-methylnitron, 28) was prepared id order to examine this abnormal photochemical behavior and also showed that it is highly resistant to UV irradiation.
