Solvatofluorochromy of cationic cyanine dyes

Ishchenko, A. A.; Svidro, V. A.; Derevyanko, N. A.

doi:10.1016/0143-7208(89)85001-6

Cited by 52 publications

(23 citation statements)

References 2 publications

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“…The solvatochromism of merocyanines 1-3 has a sign oppo site to that of the corresponding symmetrical both cat ionic (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) 14 and anionic cyanines (23-25, see Table 2) and asymmetrical cationic dyes constructed on the basis of various combinations of heterocycles involved in compounds 1-11. For example, λ max and M -1 for merocyanine 1 in CH 2 Cl 2 differ from those in DMF by 1 nm (52 cm -1 ) and 2.4 nm (136 cm -1 ), re spectively, whereas these differences for 3 are 22 nm (586 cm -1 ) and 12.5 nm (372 cm -1 ), respectively.…”

Section: Methodsmentioning

confidence: 99%

“…15 Chromatography was carried out on silica gel 60 and aluminum oxide 80 (Merck). The solvents were purified according to known procedures; 26 CH 2 Cl 2 was stabi lized by adding 1% of anhydrous ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…15 This allowed us to reliably and quantita tively characterize not only the positions (M -1 ) and in tensities ( f ) of the bands but also their shape (σ, γ 1 , γ 2 , and F ). 15 This allowed us to reliably and quantita tively characterize not only the positions (M -1 ) and in tensities ( f ) of the bands but also their shape (σ, γ 1 , γ 2 , and F ).…”

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confidence: 99%

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Synthesis and spectral properties of malononitrile-based merocyanine dyes

2005

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Di , tetra , and hexamethine merocyanines derived from malononitrile and heterocycles with moderate (dyes 1-6), strong (7-9), and weak (10 and 11) electron releasing ability were synthesized. The electronic structures of merocyanines 10 and 11 are similar to the neutral polyene state, whereas those of 7-9 are similar to the ideal polymethine state. These tenden cies become more pronounced with increasing length of the polymethine chain. The merocyanines derived from heterocyclic residues with weak or moderate electron releasing ability exhibit a positive solvatochromism, whereas those with strong electron releasing ability show a negative solvatochromism. An increase in the polarity of the solvent makes the former compounds more similar to polymethines, whereas the latter become more similar to polyenes bearing opposite charges on the end groups. The nature of the factors (nonspecific solvation, specific nucleophilic and electrophilic solvation, and vibronic interactions) responsible for the observed characteristic features was analyzed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and spectral properties of malononitrile-based merocyanine dyes

2005

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“…However, according to the literature (12), the ICG dye has solvatochromic properties. A possible loss of the symmetry of the dipole moment of the dye molecule during an interaction between solvent molecules and the dipole has been proposed, but the exact mechanism underlying the perturbation of charges in the polyamine chain is largely unknown, and there is no consensus regarding that phenomenon (13,14).…”

Section: Biophysical Journal 110(3) 723-732mentioning

confidence: 99%

Voltage-Sensitive Fluorescence of Indocyanine Green in the Heart

Martišienė

Mačianskienė

Treinys

et al. 2016

Biophysical Journal

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So far, the optical mapping of cardiac electrical signals using voltage-sensitive fluorescent dyes has only been performed in experimental studies because these dyes are not yet approved for clinical use. It was recently reported that the well-known and widely used fluorescent dye indocyanine green (ICG), which has FDA approval, exhibits voltage sensitivity in various tissues, thus raising hopes that electrical activity could be optically mapped in the clinic. The aim of this study was to explore the possibility of using ICG to monitor cardiac electrical activity. Optical mapping experiments were performed on Langendorff rabbit hearts stained with ICG and perfused with electromechanical uncouplers. The residual contraction force and electrical action potentials were recorded simultaneously. Our research confirms that ICG is a voltage-sensitive dye with a dual-component (fast and slow) response to membrane potential changes. The fast component of the optical signal (OS) can have opposite polarities in different parts of the fluorescence spectrum. In contrast, the polarity of the slow component remains the same throughout the entire spectrum. Separating the OS into these components revealed two different voltage-sensitivity mechanisms for ICG. The fast component of the OS appears to be electrochromic in nature, whereas the slow component may arise from the redistribution of the dye molecules within or around the membrane. Both components quite accurately track the time of electrical signal propagation, but only the fast component is suitable for estimating the shape and duration of action potentials. Because ICG has voltage-sensitive properties in the entire heart, we suggest that it can be used to monitor cardiac electrical behavior in the clinic.

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“…Cyanine dyes had been useful in studies of the colour of organic compounds [19] and today there are existed several fundamental principles that correlate origin of colour to chemical structures of the solute, as well as natures of the solvents [19][20][21][22]. Besides, this class of organic heterocyclic dyes compounds are useful in various industrial fields [23].…”

Section: Solvatochromismmentioning

confidence: 99%

Synthesis, Structure/Spectra Correlation and Chromism Studies of some Novel Monomethine and bis-Monomethine Cyanine Dyes

Shindy¹,

Goma²,

Harb³

2015

European Reviews of Chemical Research

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Novel methine cyanine dyes, covering monomethine and bis-monomethine cyanine dyes having the nucleus of benzo-[2,3-b;2',3'-b']-bis-furo-[2,3-d]-imidazoline-3,5,8,10-tetra were synthesized and their structure was investigated. The electronic visible absorption spectra of all the synthesized cyanine dyes were examined in 95% ethanol solution. Solvatochromism and/or halochromism for some selected dyes were investigated in pure solvents owing different polarities (water, dimethylformamide, ethanol, chloroform, carbon tetrachloride and dioxane) and/or in aqueous universal buffer solutions having varied pH values (1. 45; 2.03; 3.72; 5.09; 7.57; 8.91; 10.20 and 12.04 units), respectively. The structural determination was carried out through the elemental analysis, visible electronic absorption spectroscopy, mass spectrometry, IR, and 1 H NMR spectral data.Keywords: cyanine dyes, methine cyanine dyes, synthesis, absorption spectra, solvatochromism, halochromism. IntroductionCyanine dyes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] were and still have been the central focus of scientists in a several fields such as chemistry, biology, physics, biotechnology, engineering, pharmacology and medicine. This is due to their multi-purpose using and applications in a diverse and a broad area. Their usage and/or applications includes photographic sensitizers, laser technology, nucleic acid and protein detection, bactericides and fungicides, intercalating dyes, data storage materials; in optical devices -as photorefractive and photovoltaic sensitive materials, fluorescent probes for bio-membrane fluidity, analytical reagents over wide pH values of media, indicators and/or probes for determining the solvent polarity and as inhibitors for cell growth and cell division.Taking into consideration the above important benefits of cyanine dyes, our main goal in this research paper is the preparation of some new photosensitizers, solvatochromic and halochromic monomethine and bis-monomethine cyanine dyes, as new contribution for the synthesis and spectroscopic investigation in this field and/or may be used and applied in any of the wide application range of cyanine dyes, particularly as photographic sensitizers in photographic

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Solvatofluorochromy of cationic cyanine dyes

Cited by 52 publications

References 2 publications

Synthesis and spectral properties of malononitrile-based merocyanine dyes

Synthesis and spectral properties of malononitrile-based merocyanine dyes

Voltage-Sensitive Fluorescence of Indocyanine Green in the Heart

Synthesis, Structure/Spectra Correlation and Chromism Studies of some Novel Monomethine and bis-Monomethine Cyanine Dyes

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