Amino-substituted spirooxazine and fulgimide for the nanostructurized photochromic systems

Abstract

Comparative spectral kinetic studies of the photochromic properties of a novel N amino fulgimide and the previously synthesized aminospirooxazine intended for the synthesis of ogranic inorganic photochromic systems based on cyclotriphosphazene were performed. The results from the spectral kinetic studies evidence the fundamental suitability of these com pounds for design of the multifunctional photochromic systems based on cyclotriphosphazene. Computer molecular models of aminospirooxazine and N aminofulgimide were developed and optimization of geometric parameters was performed by the semiempirical quantum chemical method AM1.In recent years, the interest in studying nanosized struc tures for various application fields, 1 in particular, for dif ferent type optical sensors 2 and photochromic aggregated structures for nonlinear optical transformation of laser light, is enhanced. 3 One of the problems of application of photosensitive materials, including photochromic sub stances, for these purposes is design of systems with a high concentration of photosensitive elements. One of the ways for design of such systems is the synthesis of polymers containing the fragments of photochromic compounds. Another way is covalent addition of photochromes to the hybrid organic inorganic matrices. For example, it seems promising to apply as a matrix cyclotriphosphazenes (CTP) capable of supramolecular interactions. 4 Cyclo triphosphazenes are widely applied for design of various multifunctional systems. 5In this regard, we performed studies of the spectral kinetic properties of two photochromic compounds, name ly, the thermally irreversible N aminofulgimide and ther mally relaxing C aminospirooxazine, in order to deter mine the possibility of their application as photosensitive fragments for the nanostructurized photochromic systems. We also developed computer structural models of the above mentioned photochromic compounds. Results and DiscussionAs the subjects of present research, we chose the photo chromic C aminospirooxazine 1 and N aminofulgimide 2.Synthesis of photochromic compounds. Spirooxazine 1 was synthesized according to a known procedure. 6