The photodegradation of a variety of donor-acceptor-substituted azobenzene nonlinear optical chromophores has been studied. The variables examined that influence the rate of degradation include chromophore and host polymer structure, irradiation wavelength, temperature, and atmosphere.
2‐(4′‐Hydroxyphenylbenzoyl)benzoic acid is readily available from phenolphthalein by reaction with hydroxylamine. On treatment with hydrazine, 4‐(4‐hydroxyphenyl)phthalazin‐1‐one is formed in high yield. Under conditions conventionally used for the synthesis of poly(aryl ether)s the phthalazinone reacts with 4,4‐difluorobenzophenone or 4,4′‐difluorodiphenyl sulfone to yield high molecular weight linear polymers which are thermooxidatively stable and have Tg's approaching 300°C. The phthalazinone NH groups behave like phenolic OH groups and the resulting polymers contain O‐C and N‐C linkages. Phenyl‐substituted phenolphthaleins have also been synthesized and converted to the corresponding phthalazinone polymers.
The wavelength dependence of the one-photon absorption-induced photodegradation rate has been measured from the visible to the near IR for a variety of electro-optic chromophore-doped polymers. Systematic behavior is identified. The lifetime of the electro-optic activity is found to increase exponentially over 4-6 orders of magnitude for wavelengths ranging from peak of absorption, typically in the visible, to ~1000 nm. Many popular chromophores developed for electro-optics over the past 10 years are compared.
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