A novel method for the preparation of monomethine cyanine dyes

Deligeorgiev, Todor; Zaneva, D.; Katerinopoulos, Haralambos E.; Kolev, Vihren N.

doi:10.1016/s0143-7208(98)00061-8

Cited by 20 publications

(7 citation statements)

References 7 publications

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“…In this letter, we have developed an unprecedented, original two-component, one-pot approach for the synthesis of highly substituted methine cyanine dyes 3,6,7,8,9,10,11,12,14 …”

Section: Resultsmentioning

confidence: 99%

“…Thiocarbamoyls also play a decisive role in the evolution of heterocyclic chemistry and are extensively used as benecial synthons incorporating -N]C]S moiety in organic synthesis. [2][3][4][5] Additionally, for the last several years, there has been considerable progress 6,7 in the synthesis and applications of methine cyanine dyes, which are among the most inuential functional organic dyes. They have been used as photographic sensitizers, 8 optical recording materials in laser disks 9 and sensitizers in photovoltaic cells.…”

Section: Introductionmentioning

confidence: 99%

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Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

El‐Mekawy

Fadda

2017

RSC Adv.

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In this study, we have introduced an outlook dealing with synthetic heteroarenium-substituted pyridines 1 that are suitable as starting materials for the synthesis of a potential new thiocarbamoyl derivative 3 that may be of value in preparative organic and biological chemistry. Herein, a new series of twelve bis-mono and dimethine cyanine dyes incorporating different heterocyclic compounds were designed by efficient and simple reaction of compound 3 with various organic reagents to overcome the obstacles of energetic reactions, because they took long times. Moreover, the electronic behaviors of these compounds were studied because of their significant activity in many medical and other fields. The photosensitizers were elucidated by spectral and analytical analyses.

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“…In this letter, we have developed an unprecedented, original two-component, one-pot approach for the synthesis of highly substituted methine cyanine dyes 3,6,7,8,9,10,11,12,14 …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

El‐Mekawy

Fadda

2017

RSC Adv.

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“…[30][31][32][33][34][35] Some have significant drawbacks such as the evolution of methyl thiol, 30 while other methods were not appropriate for our purposes due to the absence of suitable functional groups on the N-(2,6diisopropylphenyl)-3,4-perylenedicarboximide (PMI) moiety. [30][31][32][33][34][35] Some have significant drawbacks such as the evolution of methyl thiol, 30 while other methods were not appropriate for our purposes due to the absence of suitable functional groups on the N-(2,6diisopropylphenyl)-3,4-perylenedicarboximide (PMI) moiety.…”

Section: Resultsmentioning

confidence: 99%

Enhanced Intramolecular Charge Transfer in New Type Donor–Acceptor Substituted Perylenes

et al. 2012

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Here we report the facile synthesis and physical characterization of new type N-(2,6-diisopropylphenyl)-3,4-perylenedicarboximides (PMI) with alkyl-substituted quinoline-4(1H)-ylidenemethyl or acridine-9(10H)-ylidenemethyl units as strong donors in the 9-position. When compared to parent PMI, these perylene dyes, 9-((1-methylquinoline-4(1H)-ylidene)methyl)-PMI, 9-((1-benzylquinoline-4(1H)ylidene)methyl)-PMI, 9-((1-heptylquinoline-4(1H)-ylidene)methyl)-PMI, and 9-((10-methylacridine-9(10H)-ylidene)methyl)-PMI, show a pronounced bathochromic shift of their electronic absorption with solvatochromism because of their intramolecular charge transfer. The solvatochromic behavior of these dyes is further confirmed by second-order nonlinear optical experiments. Remarkably high second-order nonlinear optical values (βHRS up to 1300 ± 50 × 10–30 esu at 880 nm in dichloromethane) are obtained by femtosecond hyper-Rayleigh scattering. The one-step synthesis together with the spectroscopic, solvatochromic, and nonlinear optical characteristics qualify these new types of perylene dyes as promising candidates for solvent polarity probes, photovoltaics, or nonlinear optical applications.

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“…Our synthesis of 3-(2-carbamoylethyl)-2-methylbenzoxazolium bromide 3e, which is the intermediate for many cyanine dyes (for example YO and the YOYOfamily), from 2-methylbenzoxazole and 1a is important because of the instability of the benzoxazolium quaternary salts in many solvents [18]. The reaction could be performed successfully in acetic anhydride due to the stability of the benzoxazole ring and the quaternization product in this medium.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel intermediates for cyanine dyes by the quaternization of -heterocycles with acrylamide and -alkyl acrylamides

2005

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A novel method for the preparation of monomethine cyanine dyes

Cited by 20 publications

References 7 publications

Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

Thiocarbamoyl in synthesis of the absorbent bis-mono and dimethine cyanine dyes incorporating porphyrin, thiazoles, thiazolones, thiadiazoles, pyrazoles and pyrazolones

Enhanced Intramolecular Charge Transfer in New Type Donor–Acceptor Substituted Perylenes

Synthesis of novel intermediates for cyanine dyes by the quaternization of -heterocycles with acrylamide and -alkyl acrylamides

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