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  Polymeric nitrons. 2. Synthesis, irradiation and waveguide mode spectroscopy of polymeric nitrons derived from polymeric benzaldehydes and N-isopropylhydroxylamine

Heinenberg, M., Menges, B., Mittler, S., & Ritter, H. (2002). Polymeric nitrons. 2. Synthesis, irradiation and waveguide mode spectroscopy of polymeric nitrons derived from polymeric benzaldehydes and N-isopropylhydroxylamine. Macromolecules, 35(9), 3448-3455.

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Heinenberg, M., Autor
Menges, B.1, Autor           
Mittler, Silvia1, Autor           
Ritter, H., Autor
Affiliations:
1MPI for Polymer Research, Max Planck Society, ou_1309545              

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 Zusammenfassung: 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 degreesC 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 hydroxyphenyl-modified polynitron (26). A low molecular weight model compound (2- hydroxybenzaldehyde-N-methylnitron, 28) was prepared in order to examine this abnormal photochemical behavior and also showed that it is highly resistant to UV irradiation.

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Sprache(n): eng - English
 Datum: 2002-04-23
 Publikationsstatus: Erschienen
 Seiten: -
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Keine Begutachtung
 Identifikatoren: eDoc: 28503
ISI: 000175112100022
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Titel: Macromolecules
  Alternativer Titel : Macromolecules
Genre der Quelle: Zeitschrift
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Affiliations:
Ort, Verlag, Ausgabe: -
Seiten: - Band / Heft: 35 (9) Artikelnummer: - Start- / Endseite: 3448 - 3455 Identifikator: ISSN: 0024-9297