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Synthesis of a polyphenol with a mesoionic 6-oxo-1,6-dihydropyrimidin-3-ium-4-olate as pendant group and its photochemical behavior

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons48202

Kobayashi,  S.
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48416

Menges,  B.
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48442

Mittler,  Silvia
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48852

Theis,  A.
MPI for Polymer Research, Max Planck Society;

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Citation

Tonami, H., Uyama, H., Kobayashi, S., Menges, B., Mittler, S., Theis, A., et al. (2003). Synthesis of a polyphenol with a mesoionic 6-oxo-1,6-dihydropyrimidin-3-ium-4-olate as pendant group and its photochemical behavior. Macromolecular Chemistry and Physics, 204(8), 1079-1084.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-61E3-2
Abstract
This study deals with synthesis of a polyphenol bearing photosensitive groups, and its photochemical behavior upon UV radiation. Mesoionic 5-(4-hydroxybenzyl)-6-oxo-1,2,3-triphenyl-1,6-dihydropyrimidin-3-ium-4-olate was prepared by condensation of 4-benzyloxybenzylmalonic acid with N,N'-diphenylbenzamidine using dicyclohexylcarbodiimide as condensing agent, followed by deprotection of the benzyl group. The monomer was polymerized by an iron-salen complex to give a polymer with a mesoionic 6-oxo-1,6-dihydropyrimidin-3-ium-4-olate moiety as the pendant group. Spin coated polymer films were prepared and characterized. It was shown by IR spectroscopy that irradiation with UV light converted the mesoionic structure to a bis(β-lactam) structure. Waveguide spectroscopy showed a large decrease in the film thickness without refractive index changes during irradiation.