Photoisomerization Dynamics of 3,3′‐Diethyl Oxacarbocyanine. Intramolecular and Solvent Viscosity Effects

Ponterini, Glauco; Caselli, Monica

doi:10.1002/bbpc.19920960410

Cited by 37 publications

(19 citation statements)

References 61 publications

(22 reference statements)

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“…For photoisomerization, the coefficient α is larger than for the thermal back isomerization (in the latter case, a weak dependence of Ea on the viscosity is observed, which is manifested only in highly viscous solvents). In [42], for photoisomerization of dye 3 in different alcohols the values of α were found to be in the range of 0.54 to 0.76, and for thermal back isomerization α ~ 0.27-0.41.…”

Section: Effect Of Solvent Viscosity On the Kinetics Of Photoisomerizmentioning

confidence: 95%

Isomerization and Properties of Isomers of Carbocyanine Dyes

Пронкин

Татиколов

2019

Sci

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One of the important features of polymethine (cyanine) dyes is isomerization about one of C–C bonds of the polymethine chain. In this review, spectral properties of the isomers, photoisomer-ization and thermal back isomerization of carbocyanine dyes, mostly meso-substituted carbocy-anine dyes, are considered. meso-Alkyl-substituted thiacarbocyanine dyes are present in polar solvents mainly as cis isomers and, hence, exhibit no photoisomerization, whereas in nonpolar solvents, in which the dyes are in the trans form, photoisomerization takes place. In contrast, the meso-substituted dyes 3,3′-dimethyl-9-phenylthiacarbocyanine and 3,3′-diethyl-9-(2-hydroxy-4-methoxyphenyl)thiacarbocyanine occur as trans isomers and exhibit photoisomerization in both polar and nonpolar solvents. The behavior of these dyes may be ex-plained by the fact that the phenyl ring of the substituent in their molecules can be twisted at some angle, removing the substituent from the plane of the molecule and reducing its steric ef-fect on the conformation of the trans isomer. In some cases, photoisomerization of cis isomers of meso-substituted carbocyanine dyes is also observed (for some meso-alkyl-substituted dyes com-plexed with DNA and chondroitin-4-sulfate; for 3,3′-diethyl-9-methoxythiacarbocyanine in moderate polarity solvents). The cycle photoisomerization–thermal back isomerization of cya-nine dyes can be used in various systems of information storage and deserves further investiga-tion using modern research methods.

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Section: Effect Of Solvent Viscosity On the Kinetics Of Photoisomerizmentioning

confidence: 95%

Isomerization and Properties of Isomers of Carbocyanine Dyes

Пронкин

Татиколов

2019

Sci

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“…Source: [i] Dempsey et al 2011; 98 [ii] Kassab 2002; 65 [iii] Cooper et al 2004; 100 [iv] Chibisov et al 1996; 70 [v] Mujumdar et al 1993; 99 [vi] Rurack and Spieles 2011; 101 [vii] unpublished data; [viii] Ponterini and Caselli 1992; 102 [ix] Jia et al 2007; 75 [x] Zheng et al 2012; 76 [xi] Chibisov 1977; 103 [xii] Roth and Craig 1974; 104 [xiii] Sanborn et al 2007; 105 [xiv] Mujumdar et al 1996; 106 [xv] Chibisov et al 1995; 107 [xvi] Gu et al 2013; 108 [xvii] Buschmann et al 2003. 67 Solvent: [a] Water; [b] Ethanol; [c] Methanol; [d] Acetonitrile; [e] Butanol.…”

Section: Figmentioning

confidence: 99%

Ultra-stable organic fluorophores for single-molecule research

et al. 2014

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Fluorescence provides a mechanism for achieving contrast in biological imaging that enables investigations of molecular structure, dynamics, and function at high spatial and temporal resolution. Small-molecule organic fluorophores have proven essential for such efforts and are widely used in advanced applications such as single-molecule and super-resolution microscopy. Yet, organic fluorophores, like all fluorescent species, exhibit instabilities in their emission characteristics, including blinking and photobleaching that limit their utility and performance. Here, we review the photophysics and photochemistry of organic fluorophores as they pertain to mitigating such instabilities, with a specific focus on the development of stabilized fluorophores through derivatization. Self-healing organic fluorophores, wherein the triplet state is intramolecularly quenched by a covalently attached protective agent, exhibit markedly improved photostabilities. We discuss the potential for further enhancements towards the goal of developing “ultra-stable” fluorophores spanning the visible spectrum and how such fluorophores are likely to impact the future of single-molecule research.

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“…In [42], for photoisomerization of dye 3 in different alcohols the values of α were found to be in the range of 0.54 to 0.76, and for thermal back isomerization α ~ 0.27-0.41.…”

Section: Effect Of Solvent Viscosity On the Kinetics Of Photoisomerizmentioning

confidence: 95%

“…In polar solvents, cyanine dyes are present in the form of free ions (cations); in this case, the influence of polarity of the medium on the isomerization of polymethine dyes is small (see above) [22,42]. However, in weakly polar and nonpolar solvents, the dyes form ion pairs with a counterion, which can affect their photochemistry, in particular, the processes of photoisomerization and back isomerization of the resulting photoisomer.…”

Section: Effects Of Ion Pair Formation On the Isomerization Processesmentioning

confidence: 99%

Isomerization and Properties of Isomers of Carbocyanine Dyes

Пронкин

Татиколов

2018

Sci

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One of the important features of polymethine (cyanine) dyes is isomerization around one of C–C bonds of the polymethine chain. In this review, spectral properties of the isomers, photoisomerization and thermal back isomerization of carbocyanine dyes, mostly meso-substituted carbocyanine dyes, are considered. meso-Alkyl-substituted thiacarbocyanine dyes are present in polar solvents mainly as cis isomers and, hence, exhibit no photoisomerization, whereas in nonpolar solvents, in which the dyes are in the trans form, photoisomerization takes place. In contrast, the meso-substituted dyes 3,3′-dimethyl-9-phenylthiacarbocyanine and 3,3′-diethyl-9-(2-hydroxy-4-methoxyphenyl)thiacarbocyanine occur as trans isomers and exhibit photoisomerization in both polar and nonpolar solvents. The behavior of these dyes may be explained by the fact that the phenyl ring of the substituent in their molecules can be twisted at some angle, removing the substituent from the plane of the molecule and reducing its steric effect on the conformation of the trans isomer. In some cases, photoisomerization of cis isomers of meso-substituted carbocyanine dyes is also observed (for some meso-alkyl-substituted dyes complexed with DNA and chondroitin-4-sulfate; for 3,3′-diethyl-9-methoxythiacarbocyanine in moderate polarity solvents). The cycle photoisomerization–thermal back isomerization of cyanine dyes can be used in various systems of information storage and deserves further investigation using modern research methods.

show abstract

Photoisomerization Dynamics of 3,3′‐Diethyl Oxacarbocyanine. Intramolecular and Solvent Viscosity Effects

Cited by 37 publications

References 61 publications

Isomerization and Properties of Isomers of Carbocyanine Dyes

Isomerization and Properties of Isomers of Carbocyanine Dyes

Ultra-stable organic fluorophores for single-molecule research

Isomerization and Properties of Isomers of Carbocyanine Dyes

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