Ormosils (Organically Modified Silicates) have been used in the past as hosts for various organic molecules. In this work, seven different photochromic dyes most of which belong to the spirooxazine / merocyanine family were doped into thin films that were prepared using several increasingly inorganic Ormosil formulations. These dyes were either physically incorporated into the pores of the film or covalently bound to the matrix via a siloxane substituent. The dyes, which undergo a reversible color change upon irradiation, are relatively stable, although they will ultimately degrade after prolonged exposure to ultraviolet irradiation. This work focuses on identifying the variables that influence the rate of dye degradation, including rigidity of the Ormosil matrix, wavelength of irradiation, and the presence of oxygen. The silylated dyes, which are generally regarded as having reduced mobility within the pores of the Ormosil, degraded more slowly, suggesting a link between stability and rotational and translational freedom. Irradiation wavelength also affected dye stability in that limiting exposure to wavelengths in the near UV (and eliminating visible light) causes the least degradation. This is attributed to the photostability of the photomerocyanine isomer. Finally, the presence of oxygen was shown to cause dramatic enhancement in degradation. The mechanisms of each of these effects are discussed.
Worcester Polytechnic Institute
Chemistry & Biochemistry
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Koppetsch, Karsten J., "Photodegradation of Organic Photochromic Dyes Incorporated in Ormosil Matrices" (2000). Masters Theses (All Theses, All Years). 795.
photochromic, spirooxazine, Ormosil, Photochromism, Dyes and dyeing, Photochromic materials, Photochemistry