27333-47-7Relevant articles and documents
Synthesis of photochromic spirooxazines from 1-amino-2-naphthols
Lokshin, Vladimir,Samat, Andre,Guglielmetti, Robert
, p. 9669 - 9678 (1997)
A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2- naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to further spiroheterocyclic oxazines are possible.
Photochromic Processes in Spiro(1,3,3-trimethylindolo-2,2'-naphth-1,4-oxazine) studied using Two-laser Two-colour Techniques
Bohne, C.,Fan, M. G.,Li, Z. J.,Lusztyk, J.,Scaiano, J. C.
, p. 571 - 572 (1990)
The photochemistry of the photomerocyanine from the title compound shows dramatic differences between polar and non-polar media; in the latter it involves the intermediacy of a ground state species with a lifetime of ca. 4 μs which regenerates the merocyanine almost quantitatively.
Structures and photochromic properties of substituted spiroindolinonaphthoxazines
Aldoshin,Chuev,Filipenko,Utenyshev,Lokshin,Laregenie,Samat,Guglielmetti
, p. 1089 - 1097 (1998)
Six indolinospironaphthoxazines were studied by X-ray diffraction analysis. It was demonstrated that the electronic nature of the substituents in the naphthoxazine and indoline fragments has no substantial effect on the Cspiro-O and Cspiro-N bond lengths. Photocolorability of the compounds under study depends only slightly on the above-mentioned bond lengths and correlates mainly with the energy of steric strain of the oxazine ring. The stability of the open forms of spiroindolinonaphthoxazines that formed upon photoirradiation is determined to a large extent by the electronic and steric nature of the substituents. The exception is the compound that contains the NO2 group in the indoline fragment. In the last-mentioned case, the cleavage of the ring occurs through a substantially different pathway.
A method for synthesizing spiroxime photochromic dyes using a microchannel reactor
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Paragraph 0032-0034, (2022/01/20)
The present invention relates to a method of synthesizing a photochromic dye using a microchannel reactor. In the coupling ring process in the late stage of dye synthesis, after the temperature of the mobile phase system containing the reaction raw material is adjusted to the reaction temperature by the pre-reaction system, the above-mentioned mobile phase is pumped into the microchannel reactor by means of a constant current pump for mixed temperature control reaction, and a solution containing photochromic dye is obtained, and the photochromic dye is obtained by concentration, recrystallization, decolorization and drying. This method uses the high mixing and heat exchange efficiency of the microchannel to ensure the full mixing of the reactants and the accuracy of temperature control, the energy saving effect is good, the production cost is reduced, the purity of the product is high, the difficulty of subsequent processing is reduced, the mobile phase can be reused, and it is convenient for large-scale production, which has a broad application prospect.
Spiropyrans and spirooxazines and preparation method thereof
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Paragraph 0074; 0076; 0080; 0081; 0124; 0125, (2019/01/22)
The invention provides spiropyrans, naphthospiropyrans and spirooxazines. The invention also relates to a method for preparing the spiropyrans, the naphthospiropyrans and the spiroxazines by reactionof indole compounds, especially indole iodide, with alde
Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
Balmond, Edward I.,Tautges, Brandon K.,Faulkner, Andrea L.,Or, Victor W.,Hodur, Blanka M.,Shaw, Jared T.,Louie, Angelique Y.
, p. 8744 - 8758 (2016/10/14)
Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.
