We demonstrate holographic recording in a new photopolymer system. The recording material is created by copolymerization of an optically inert monomer, methyl methacrylate, and a second monomer that is optically sensitive. On exposure of the recording material to light, a portion of the optically sensitive component detaches from the polymer matrix and causes hologram amplif ication through diffusion of the free molecules. We measured postrecording grating amplif ications as high as 170% by this process. The recorded holograms are persistent at room temperature under continuous illumination at the recording wavelength.
Thiofluorescein was synthesized in a preparative yield by successive demethylation of 3,3'-dimethoxydiphenyl sulfide to 3,3'-dihydroxydiphenyl sulfide and condensation of the latter with phthalic anhydride in H 2 SO 4 . The title compound was also obtained in a higher yield from 3,3'-dimethoxydiphenyl sulfide directly in a one-pot process combining the condensation in H 2 SO 4 and demethylation in 2 Py · H 2 SO 4 .Bromo-and iodo-substituted xanthene dyes are used in photopolymerization processes [14] due to high yield of the triplet state which gives rise to effective electron transfer from the donor molecule with formation of free radicals. Analogous increase in the yield of the triplet excited state is attained by replacement of the ring oxygen atom in Fluorescein by sulfur (Thiofluorescein) [5].A reliable synthesis of Thiofluorescein (3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-[9H]thioxanthen]-3-one) was reported for the first time in patent [6]. 3,3'-Dimethoxydiphenyl sulfide (I) obtained by reaction of sodium 3-methoxybenzenethiolate with 3-iodo-1-methoxybenzene was demethylated to 3,3'-dihydroxydiphenyl sulfide (II), and the latter was brought into condensation with phthalic anhydride in 80% sulfuric acid. However, neither the yield nor other parameters of the condensation product were given. According to Pfoertner [7], the condensation of sulfide II with phthalic anhydride was performed in molten ZnCl 2 , but no experimental procedure was given. Eltsov et al. [5] synthesized Thiofluorescein (III) using as starting compound sulfide I rather than II. The condensation and demethylation stages were combined into a onepot process which was carried out in 80% sulfuric acid. The target product was isolated in 32% yield after triple reprecipitation, washing, dissolution, filtration, and additional purification. The product was characterized only by the analytical data (C, H) and molar absorption coefficient in a sodium hydroxide solution.The goal of the present work was to experimentally check the above procedures for the synthesis of Thiofluorescein (III) and improve them using both methoxy sulfide I and hydroxy sulfide II as initial compound. The first stage in the synthesis of Thiofluorescein (III) is preparation of sulfides I and II. According to the data of [57], sulfide I was obtained by heating a mixture of sodium-3-methoxybenzenethiolate with 3-iodo-1-methoxy-benzene (Scheme 1) above 200°C in the presence of copper powder [8]. Our attempts to reproduce this procedure showed that the yield of sulfide I does not exceed 52%. Schopfer and Schlapback [9] proposed to use tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 as efficient catalyst for analogous condensations. Under the conditions reported in [9] [100°C, Pd 2 (dba) 3 ], we synthesized sulfide I in 80% yield.Demethylation of I was effected [6,7] by treatment with hydrogen iodide in acetic acid. We applied a more 0H2 6+ , 20H 3G GED '3(SKRV W%X2. 3K0H R & K 6 0H2 20H , Scheme 1. Deceased.DPEphos is 2,2'-bis(diphenylphosphino)diphenyl ether.
A new holographic photopolymer material is developed. The photopolymer material is sensitized by dyes of xanthene and thioxanthene series which contain iodine and bromine heavy atoms. Holographic recording was carried out during excitation of forbidden singlet–triplet electron transitions of dyes. Thioerythrosin triethylammonium was identified as the most effective sensitizer among a number of tested dyes. The spectral absorption area of the singlet–triplet electronic transition of the dye is conveyed in the red spectral range from 600 to 700 nm. The sensitivity of the photopolymer material to radiation with 633 nm wavelength is 180 mJ cm−2. Optimization of concentration of the main components of the photopolymer compositions was carried out in order to achieve maximum efficiency of holographic recording.
No abstract
Photoactive 4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts were synthesized by alkylation of 3-chloro-2-(piperazin-1-yl)-and 2-arylamino-3-(4-methylpiperazin-1-yl)-1,4-naphthoquinones. Light sensitivities of materials obtained by adsorption of the synthesized piperazinium salts from solution onto oxidized aluminum support were estimated. R = C 4 H 9 (a), C 5 H 11 (b), C 7 H 15 (c), C 10 H 21 (d), NCCH 2 CH 2 (e), PhCH 2 (f), MeCH(OH)CH 2 (g), ClCH 2 CH(OH)CH 2 (h), Me (i).2-Dialkylamino-1,4-naphthoquinone derivatives are known to exhibit photochemical activity [1,2], and some compounds of this series were proposed as lightsensitive components of non-silver photographic materials [3, 4]. With a view to extend the scope of application of 2-dialkylamino-1,4-naphthoquinones via improvement of their solubility in water, arylamino groups containing a carboxy or sulfo group were introduced into the quinoid ring [5] or a sulfo group was introduced into the aromatic ring of 1,4-naphthoquinone [6][7][8]. In the present work we tried to synthesize amphiphilic derivatives of dialkylamino-1,4-naphthoquinones by quaternization of 2-(piperazin-1-yl)-substituted 1,4-naphthoquinones. Appearance of a positive charge on the piperazine fragment converts neutral molecule into organic salt and enhances its hydrophilicity, so that the piperazine fragment becomes hydrophilic while the naphthoquinone fragment remains hydrophobic.It is known [9] that in most cases quaternization of tertiary amines with alkyl halides is not complicated provided that the basicity of the amine is sufficiently high and that there are no unfavorable steric factors. The most probable site of electrophilic attack by alkyl halide on 2-(piperazin-1-yl)-1,4-naphthoquinone molecule is the nitrogen atom linked to alkyl substituent rather than that linked to the naphthoquinone fragment. By reactions of 3-chloro-2-(piperazin-1-yl)-1,4-naphthoquinone (I) with butyl bromide, benzyl chloride, and 1,2-epoxypropane in the presence of a base we previously obtained only monoalkylation products, whereas the reaction with methyl iodide gave quaternary salt.In the present work quaternary 4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts were synthesized by double alkylation of quinone I using an extended series of alkylating agents (alkyl halides and 1-chloro-2,3-epoxypropane). The reaction of I with
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