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Synthesis And Structure Identification Of Photochromic Bisspirooxazine And Oxazine

Posted on:2012-08-05Degree:MasterType:Thesis
Country:ChinaCandidate:R Y YueFull Text:PDF
GTID:2211330338460336Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Photochromism is defined as a reversible phototransformation of a chemical species between two forms having different absorption spectra. Photochromism is a new scientific field born in 90's of twentieth century. It is an interdispline field based on the research of chemistry, physics, materials and photoelectronic technology.During the last decade, organic photochromic compounds have increasingly attracted more attention and interest of chemists and engineers due to their potential applications, especially in optical information storage.This thesis mainly consists of three parts, It may be summarized as follows:In the first part, a brief introduce of the development process a of the organic photochromic compounds, introduced a new oxazine compounds and a series of spiropyranand spirooxazine through the modified, and reviews the recent progress in the study of the photochromic polymers.In the second part, indole was synthesized from aniline diazotization, reduction, Fisher synthesis, and synthesized a series of oxazine compounds with 2-chloromethyl-4- nitrophenol.2- nitro-5a,6,6-trimethyl-5a,6-dihydro-12H-indole [2,1-b] [1,3] oxazine and naphthalene and 2-nitro-5a,6,6- trimethyl-5a,6- dihydro-8- chloro-12H-indole [2,1-b] [1,3] benzoxazine not been reported, the structure of the target product was confirmed by NMR,MS and IR.1-chloromethyl-2-naphthol was synthesized from 2-naphthol, and reaction,with the indole,the results show that oxazine compounds have not been from.In the third part,2,3,3,6,7,7-hexamethyl-3,7-dihydropyrrolo[2,3-f]indole (bisindole)was synthesized from p-phenylenediamine.1,3,3,5,7,7-hexamethyl-2,6-dimethyl-1,2,3,5,6,7-hexahydro pyrrolo [2,3-f] indole was synthesised by methylation. Bisoxazine was synthesized by bisindole and 2-chloromethyl-4- nitrophenol. 1,3,3,5,7,7-hexamethyl-2,6-dimethylene-1,2,3,5,6,7-hexahydro pyrrolo [2,3-f] indole with 1-nitroso-2-naphthol reaction of the double spiraloxazine. Try using 2,2-bis (4-hydroxyphenyl) propane as the raw material to synthesize 2,2- bis (3-nitroso-4-hydroxyphenyl) propane, the result of 2-(4-hydroxyphenyl)-2-(3-NO2-4- hydroxyphenyl) propane(single nitro compound)and 2,2-bis (3-nitro-4-hydroxyphenyl) propane (two nitro compounds). References synthesis of 2,2-bis (3-formyl-4-hydroxyphenyl) propane (bissalicylaldehyde), bissalicylaldehyde and 1,3,3,5,7,7 hexamethyl-2,6-methyl-1,2,3,5,6,7-hexahydro pyrrolo [2,3-f] indole was used as raw material to synthesis of photochromic polymers. We found it requires further research.
Keywords/Search Tags:Photochromism, Oxazine, Bisspirooxazine synthesis, Characterization
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