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

Deligeorgiev, Todor; Vasilev, Aleksey; Drexhage, K. H.

doi:10.1016/j.dyepig.2004.09.013

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…Several novel heterocyclic N ‐2‐hydroxypropyl quaternary salts ( 7 , 8 ) have been prepared by the reaction of propylene oxide or epichlorohydrin ( 6 ) with the appropriate heterocyclic base ( 4 , 5 ) in the presence of perchloric or hydrobromic acid (Scheme 2) [5]. The quaternisation of different N ‐heterocycles ( 9 , 10 ) with acrylamide ( 11 ) or N ‐alkyl acrylamide has also been described (Scheme 3) [6], resulting in compounds 12 and 13 .…”

Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

“…Several novel heterocyclic N-2-hydroxypropyl quaternary salts (7,8) have been prepared by the reaction of propylene oxide or epichlorohydrin (6) with the appropriate heterocyclic base (4,5) in the presence of perchloric or hydrobromic acid (Scheme 2) [5]. The quaternisation of different N-heterocycles (9,10) with acrylamide (11) or N-alkyl acrylamide has also been N X + R-I CH 3 CN, reflux 24 h N + X R I -X = S, Se, O, C(CH 3 ) 2, CH=CH; R = C 2 H 5, C 6 H 13, C 10 H 21 described (Scheme 3) [6], resulting in compounds 12 and 13. N-Alkylphosphonate quaternary ammonium salts are novel precursors for cyanine dyes, with heterocycles bearing a phosphonate moiety as the N-substituent obtained by a classical nucleophilic substitution reaction (Scheme 4) [7].…”

Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

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Styryl dyes – synthesis and applications during the last 15 years

Deligeorgiev

Vasilev

Kaloyanova

et al. 2010

Coloration Technology

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One of the most widely used and important groups of functional dyes are the styryl dyes and a review of this functional dye class has not been published for more than 15 years. In this review article, we describe the new trends in the synthesis of a range of novel intermediates and styryl dyes and include the most interesting examples of their high‐tech applications. However, this review is not intended to be comprehensive because of the large number of styryl dye studies that have been carried out in this time. Styryl cyanine dyes are widely used in optical recording media in laser discs, as flexible dyes, laser dyes, as optical sensitisers and in various other fields, for example dye‐sensitised solar cells and dyes with non‐linear optical properties. Additionally, the most important applications for these dyes are in bio‐labelling and in medicinal analysis.

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Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

Section: Intermediates For Styryl Dyesmentioning

confidence: 99%

Styryl dyes – synthesis and applications during the last 15 years

Deligeorgiev

Vasilev

Kaloyanova

et al. 2010

Coloration Technology

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“…Hemicyanine dyes (Kim, 2006;Hammer, 1964;Raue, 1990;Pardal et al, 2002;Deligeorgiev, 2005;Mazinres, 2007;Nagarajan, Perumal, 2004;Lai et al, 1997;Kabatc et al, 2015;Malegoll et al, 2005;Narayan, Ansari, 2008;Davis et al, 2004) are one of the most widely used and important class of functional dyes. They are used as sensitizers and other additives in the photographic industry, chemosensors, indicator dyes, in optical recording media in laser disks, as flexible dyes, in textile industry, laser dyes, as optical sensitizers and in various other fields, for example dye-sensitized solar cells and dyes with non-linear optical properties.…”

Section: Introductionmentioning

confidence: 99%

Novel Hemicyanine and Aza-Hemicyanine Dyes: Synthesis, Spectral Investigation and Antimicrobial Evaluation

2016

European Journal of Molecular Biotechnology

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Novel hemicyanine dyes and aza-hemicyanine dyes having the nucleus of furo [(3,2- )imidazol] iodide salt were prepared. The electronic visible absorption spectra of all the synthesized hemicyanine dyes and aza-hemicyanine dyes were investigated and in 95 % ethanol solution to evaluate their spectral characterization. The antimicrobial effects of some selected dyes were tested against various bacterial and fungal strains (Escherichia coli, Staphylococcus aureus, Aspergillus flavus and Candida albicans) to assess their antimicrobial (bactericidal and fungicidal) properties. The results discussed in this study revealed that both the spectral characterization and the antimicrobial properties of the examined dyes is highly effected by the type of the X substituted in the phenyl ring system for the hemicyanine dyes and by the type of the phenyl and/or the naphthyl ring system for the aza-hemicyanine dyes. Structural confirmations were identified by elemental analysis, visible spectra, IR and 1 H NMR spectroscopic data.Keywords: cyanine dyes, hemicyanine dyes, synthesis, absorption spectra, antimicrobial activity, aza-hemicyanine dyes. IntroductionHemicyanine dyes (Kim, 2006;Hammer, 1964;Raue, 1990; Pardal et al., 2002;Deligeorgiev, 2005;Mazinres, 2007;Nagarajan, Perumal, 2004; Lai et al., 1997;Kabatc et al., 2015;Malegoll et al., 2005; Narayan, Ansari, 2008;Davis et al., 2004) are one of the most widely used and important class of functional dyes. They are used as sensitizers and other additives in the photographic industry, chemosensors, indicator dyes, in optical recording media in laser disks, as flexible dyes, in textile industry, laser dyes, as optical sensitizers and in various other fields, for example dye-sensitized solar cells and dyes with non-linear optical properties. The most important applications for these dyes are in bio-labeling and in medicinal analysis. In addition, hemicyanine dyes (Davis et al., 2004;Shindy, Koraiem, 2008;Shindy et al., 2014;Davis et al., 2006;Wuskell et al., 2006;Banerji et al., 1982;Jha, Banerji, 1985;Jha, 1986;Heilbron, Walter, 1925;Ren et al., 2012; Shindy, 2015;Shindy, 2007) is common fluorescence probe for electrical membrane potential in biochemistry and biophysical area. It is also a very important fluorescence dyes applied in lasers, molecular electronics and nonlinear optical photolimiting devices. Besides,

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References

2010

Handbook of Heterocyclic Chemistry

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

Cited by 10 publications

References 14 publications

Styryl dyes – synthesis and applications during the last 15 years

Styryl dyes – synthesis and applications during the last 15 years

Novel Hemicyanine and Aza-Hemicyanine Dyes: Synthesis, Spectral Investigation and Antimicrobial Evaluation

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