Benzodipyrrolenine-based biscyanine dyes: Synthesis, molecular structure and spectroscopic characterization

Klochko, Oleksiy P.; Fedyunyayeva, Iryna A.; Khabuseva, S.U.; Semenova, O.; Terpetschnig, Ewald; Patsenker, L. D.

doi:10.1016/j.dyepig.2009.09.007

Cited by 16 publications

(18 citation statements)

References 26 publications

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“…Because of this the delocalized positive charge in bis-styryl molecules 3ae3c is shifted from the terminal nitrogens (q Term ) to the central benzodipyrrolenine nitrogens (q Centr ), which results in a positive Dq ¼ q Centr À q Term (Table 2). At the same time opposite effect (negative Dq) was observed for bistrimethine dyes such as 1a, where a positive charge predominated on the terminal heterocyclic end-groups [18].…”

Section: Molecular Structuresmentioning

confidence: 94%

“…Similarly to bis-trimethine dyes 1ae1e [18], the spinespin coupling constant (J) of the methine hydrogens are in the range of 13.5e15.0 Hz indicating that the polymethine chain in both series 3ae3c and 4ae4c is in all-trans conformation. This conformation seems not to depend on the terminal end-groups (1a, 3a, 3b, 4a, 4b) or the chain length (dimethines 3a and 4a or tetramethines 3c and 4c).…”

Section: Molecular Structuresmentioning

confidence: 96%

“…4-(3,5-diphenyl-4,5-dihydro-1H-1-pyrazolyl) benzaldehyde was synthesized according to [37]. 2-(3-1,3,3,5,7,7-hexamethyl-6-[3-(1,3,3-trimethyl-3H-2-indoliumyl)-2-propenylidene]-1,2,3,5,6,7-hexahydropyrrolo[2,3-f]indol-2-yliden-1-propenyl)-1, 3,3-trimethyl-3H-indolium (1a) was synthesized according to [18]. Other chemicals, reagents and solvents were from Merck.…”

Section: Generalmentioning

confidence: 99%

“…Recently we reported the synthesis, molecular structures and spectral properties of a series of bis-trimethine cyanine dyes 1ae1e (Scheme 1) all containing a centrosymmetrical benzodipyrrolene moiety and variable terminal heterocyclic end-groups [18]. Conjugation of two uniform "monomeric" trimethine chromophores to form a bis-trimethine molecule was found to cause splitting of the long-wavelength absorption band of the parent "monomeric" dye into two bands, which was in good agreement with Kiprianov's theory [17].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

et al. 2011

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Section: Molecular Structuresmentioning

confidence: 94%

Section: Molecular Structuresmentioning

confidence: 96%

Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

et al. 2011

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“…Cyanine dyes [1][2][3][4][5][6][7][8][9][10][11][12][13][14] are a class of organic heterocyclic dyes, which have long captured the interest of the scientific community. This is because the class of cyanine dyes has proved to be particularly useful in a diverse and a broad area of science, technology and engineering.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photosensitization Evaluation of Some Novel Polyheterocyclic Cyanine Dyes

Shindy¹,

Khalafalla²,

Goma³

et al. 2015

European Reviews of Chemical Research

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New polyheterocyclic compound, namely 4-methyl-6-oxo-2-phenyl-furo [(3,2-d)pyrazole; (  3 ,  2 -d) imidazole] was prepared and oriented to synthesis of some novel monomethine cyanine dyes, dimethine cyanine dyes and mono/di-mixed methine cyanine dyes. The electronic visible absorption spectra of all the synthesized cyanine dyes were investigated in 95% ethanol solution to evaluate their photosensitization properties. Structural identification was carried out via the elemental analysis, visible spectra, mass spectrometry, IR and 1 H NMR spectroscopic data.Keywords: cyanine dyes, synthesis, photosensitization, monomethine cyanine dyes, dimethine cyanine dyes, mixed methine cyanine dyes. IntroductionCyanine dyes [1][2][3][4][5][6][7][8][9][10][11][12][13][14] are a class of organic heterocyclic dyes, which have long captured the interest of the scientific community. This is because the class of cyanine dyes has proved to be particularly useful in a diverse and a broad area of science, technology and engineering. Their uses and applications includes but not limited to color and non color (black and white) photography, in high energy laser and digital image storage, analytical reagents over a wide range of pH of media, indicators for solvent polarity, in biological and biomedical use as molecular probes and as fluorescent dyes commonly used for DNA visualization assays. In addition, cyanine dyes [15][16][17][18][19][20][21][22][23][24][25][26][27][28] are widely used as optical recording materials, thermal writing display, laser printers, laser filters, absorptivity and antimicrobial efficiency, for probing lipophilic environments, halophobic pockets of enzymes and components of supramolecular structures.Taking into account and consideration the above significant benefits of cyanine dyes, in this research paper we prepared new photosensitizers cyanine dyes as new synthesis contribution and spectroscopic investigation in this field and may be used and/or applied in any of the wide mentioned application field of cyanine dyes, particularly as photographic sensitizers in photosensitive material industry, as probes for determining solvent polarity in solution chemistry, and/or as indicators in operations of acid/base titrations.

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Chemical Sensors and Probes for Bioimaging

2023

Sensors and Probes for Bioimaging

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Benzodipyrrolenine-based biscyanine dyes: Synthesis, molecular structure and spectroscopic characterization

Cited by 16 publications

References 26 publications

The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

The synthesis, structure and spectral properties of new long-wavelength benzodipyrroleninium-based bis-styryl dyes

Synthesis and Photosensitization Evaluation of Some Novel Polyheterocyclic Cyanine Dyes

Chemical Sensors and Probes for Bioimaging

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