Study On Preparation And Photochromic Properties Of1,3,3-trimethylspiro [Indoline-2,3’-naphth-[2,1-b][1,4] Oxazine]

Organic photochromic materials arising from the many potential applications, it is a major issue in the field of new materials. Such materials with reversible photochromic which are associated with their ability to undergo reversible, light-induced color change. Two chemical species showing reversible transformation differ from one another not only in the absorption spectra but in their physical and chemical properties as well. Organic photochromic materials are used most widely in ophthalmic sun-screening applications, and also find applications in security printing, optical recording and switching, solar energy storage, nonlinear optics and biological systems. Spirooxazines are a particularly significant group of organic photochromic materials. However, the synthesis method affords Spirooxazines in low yields, and their photoeolorability and fatigueresistanee must be promoted for the practical application. Based on these, this paper focuses on the synthesis process of the spirooxazine compounds and photochromic properties.Our research work initial focused on the synthesis of1,3,3-trimethyl-spiro [indoline-2,3’-naphth [2,1-b][1,4] oxazine](TMSO).2-naphthol, phenylhydrazine,3-methyl-2-butanone and1-amino-2-naphthol (ANP) were selected as main starting materials for synthesis of TMSO. The synthesis process on key intermediates such as1-nitroso-2-naphthol (NNP),2,3,3-trimethyl-3H-indole (TMI),1,2,3,3-tetramethyl-3H-indole iodide(TMII),1,3,3-trimethyl-2-methylene-indoline (TMMI) and target compound TMSO were researched By orthogonal test and single factor test, and their optimum conditions were geted. The nealy colorless single crystal of TMSO was prepared successfully. The new synthesis method to improve the yield (yield:50.2%、75.0respectively), mild reaction conditions, and the operation is simple and it was suitable for practical manufacture. The structures of compounds were confirmed by EA, HPLC, FT-IR,1H-NMR, MS and XRD.In addition to photochromic properties of TMSO in solid and liquid states were studied, the influence of external factors such as concentration of solution, pH value, polarity of solvents, temperature, polymer medium etc were investigated. These research results provide some new ideas to improve photochromism of other Spirooxazines (SO) compounds.