Photochemistry of 2-dialkylamino-1,4-naphthoquinones

Shishkina, R. P.; Berezhnaya, V. N.

doi:10.1070/rc1994v063n02abeh000076

Cited by 6 publications

(5 citation statements)

References 9 publications

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“…When it is illuminated, N-naphthoquinonylamine undergoes a transformation first to a metastable state before it is transformed into its final stable form. 8 A portion of the chromophore detaches from the polymer and is free to diffuse as discussed above.…”

Section: -3mentioning

confidence: 99%

Holographic recording in a photopolymer by optically induced detachment of chromophores

et al. 2000

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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. 

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Section: -3mentioning

confidence: 99%

Holographic recording in a photopolymer by optically induced detachment of chromophores

et al. 2000

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“…In the present work reactions of quinones I and III with amines were examined with a view to elucidate regioselectivity of the process. By analogy with light-sensitive amino-substituted 1,4-naphthoquinones [14], the resulting aminothioxanthenones could be promising as nonsilver photographic materials.…”

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Amination of thioxanthene-1,4,9-trione and its chloro derivatives

Loskutov

2011

Russ J Org Chem

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Thioxanthene-1,4,9-trione and its 2(3)-chloro and 2,3-dichloro derivatives reacted with amines to give the corresponding 2-amino-substituted products.R 1 = H, R 2 = Ph (a); R 1 = H, R 2 = 4-BuC 6 H 4 (b); R 1 = H, R 2 = cyclohexyl (c); R 1 R 2 N = piperidino (d).Quinones are known to react with amines according to nucleophilic 1,4-addition pattern with intermediate formation of aminohydroquinones which undergo oxidation with the initial quinone (or other oxidant) to give aminoquinones [1][2][3]. The site of nucleophile addition to benzo-, naphtho-, and anthraquinones is obvious, whereas formation of different regioisomers is possible in reactions with unsymmetrical quinones, e.g., those in which the quinoid ring is fused to a heteroring or a substituted benzene ring. In these cases, the quinone carbonyl groups are nonequivalent, and each of them may be involved in nucleophile addition at the conjugated bond system. In this respect, nitrogen-containing heterocyclic quinones were studied most thoroughly; the direction of their reactions with amines is determined by the solvent nature, substitution pattern in the substrate, and catalysis by metal salts. A classical example illustrating the above stated is given by 5,8-quinolinequinone and its monochloro derivatives [4]. Unsubstituted 5,8-quinolinequinone reacts with aniline to produce addition products at positions 6 and 7 at a ratio of ~1 : 1 (in ethanol) or 6.5 : 1 (in acetic acid), whereas 6-phenylamino derivative is formed exclusively in the presence of CeCl 3 · 7 H 2 O as catalyst (in ethanol). 6-Chloro-5,8-quinolinequinone in the absence of catalyst reacts mainly according to the addition pattern to form 7-phenylamino derivative, while replacement of the 6-chlorine atom becomes the only process under catalytic conditions. 7-Chloro-5,8-quinolinequinone is converted into 7-chloro-6-phenylamino derivative as the only product both in the absence and in the presence of catalyst. Analogous studies were performed for other nitrogencontaining quinones, such as indole-4,7-quinone [5], isoquinoline-5,8-quinone [6], and phenanthridine-7,10-quinone [7], as well as for 5-substituted 1,4-naphthoquinones [8].There are no published data on the regioselectivity of amination of sulfur-containing heterocyclic quinones. Known quinones of the thioxanthene series are thioxanthene-1,4,9-trione (I), which is available via oxidation of 1,4-dihydroxythioxanthen-9-one (II) with potassium bromate [9], ammonium cerium(IV) nitrate [10], or moist iodous acid [11], and its 2,3-dichloro derivative III obtained by oxidative chlorination of thioxanthenone II with molecular chlorine [12] or

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“…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].…”

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“…A practically important property of the synthesized quaternary piperazinium salts is their ability to undergo photochemical reduction [1,2]. Therefore, we estimated photosensitivity of these salts by preparing materials in which latent image is obtained via reductive formation of catalytically active centers (materials with physical development of latent image).…”

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confidence: 99%

“…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].…”

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Synthesis of photoactive 1-methyl-1-R-4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts

2011

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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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Photochemistry of 2-dialkylamino-1,4-naphthoquinones

Cited by 6 publications

References 9 publications

Holographic recording in a photopolymer by optically induced detachment of chromophores

Holographic recording in a photopolymer by optically induced detachment of chromophores

Amination of thioxanthene-1,4,9-trione and its chloro derivatives

Synthesis of photoactive 1-methyl-1-R-4-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)piperazinium salts

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