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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

✍ Scribed by Hiroyuki Tonami; Hiroshi Uyama; Shiro Kobayashi; Bernhard Menges; Silvia Mittler; Alexander Theis; Helmut Ritter

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 126 KB
Volume: 204
Category: Article
ISSN: 1022-1352
DOI: 10.1002/macp.200390076

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✦ Synopsis

Abstract

This study deals with the synthesis of a polyphenol bearing photosensitive groups, and its photochemical behavior upon UV irradiation. 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.

Time development of the refractive index and the film thickness measured with p‐polarized light.

magnified imageTime development of the refractive index and the film thickness measured with p‐polarized light.

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