Solvent effects on the nonlinear optical response of a potentiometric biological imaging dye

Li, Haowen; Mao, Guilin; Singer, Kenneth D.; Lu, Zhiyuan; Weber, Ryan; Twieg, Robert J.

doi:10.1364/josab.24.001310

Cited by 11 publications

(7 citation statements)

References 39 publications

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“…Polar solvents, on the other hand, are usually able to stabilize the excited state of a molecule by reorientation of the solvent molecules, which leads to a decreased energy of the excited state, resulting in an emission at longer wavelength compared to the wavelength in a less polar solvent (i.e., up to hexanol). These solvatochromic effects were seen for all three probes, and the results are consistent with previous studies, where separate probes have been studied with respect to effects of polarity on the spectral properties. − When comparing the three probes, they all show the same trend in absorbance and emission wavelength. The trend is, however, broken for di-8-ANEPPS, which shows a decreased Stokes’ shift in water compared to methanol due to a blue-shift of the emission wavelength.…”

Section: Discussionsupporting

confidence: 90%

“…35 The red-shift of absorption is also seen for di-8-ANEPPS in solutions of decreased DMSO/chloroform ratio (and hence decreased polarity). 33 When salt concentration is increased, a blue-shift of the absorbance of RH421 occurs, whereas the fluorescence has been observed to decrease and red-shift. 28 In this study, we examine three commonly used and wellstudied styryl-dyes, di-4-ANEPPS, di-8-ANEPPS, and RH421 (see Figure 1) and characterize their binding geometries in two different model membranes: in the lipid bilayer of large unilamellar lipid vesicles (LUVs) and in a lamellar liquid crystal system.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The absorbance as well as fluorescence spectra of voltage-sensitive probes have been shown to be generally sensitive to their local environment. ,,,− Parameters such as solvent polarity, − pH, , and ionic strength , have been shown to be important not only for the absorption and emission wavelengths and for the emission intensity of the dyes, but also for the fluorescence lifetime. ,− ,, For example, the absorption of RH421 red-shifts when the solvent polarity decreases, whereas the fluorescence displays a blue-shift under the same conditions . The red-shift of absorption is also seen for di-8-ANEPPS in solutions of decreased DMSO/chloroform ratio (and hence decreased polarity) . When salt concentration is increased, a blue-shift of the absorbance of RH421 occurs, whereas the fluorescence has been observed to decrease and red-shift …”

Section: Introductionmentioning

confidence: 99%

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Spectral Properties and Orientation of Voltage-Sensitive Dyes in Lipid Membranes

et al. 2012

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Voltage-sensitive dyes are frequently used for probing variations in the electric potential across cell membranes. The dyes respond by changing their spectral properties: measured as shifts of wavelength of absorption or emission maxima or as changes of absorption or fluorescence intensity. Although such probes have been studied and used for decades, the mechanism behind their voltage sensitivity is still obscure. We ask whether the voltage response is due to electrochromism as a result of direct field interaction on the chromophore or to solvatochromism, which is the focus of this study, as result of changed environment or molecular alignment in the membrane. The spectral properties of three styryl dyes, di-4-ANEPPS, di-8-ANEPPS, and RH421, were investigated in solvents of varying polarity and in model membranes using spectroscopy. Using quantum mechanical calculations, the spectral dependence of monomer and dimer ANEPPS on solvent properties was modeled. Also, the kinetics of binding to lipid membranes and the binding geometry of the probe molecules were found relevant to address. The spectral properties of all three probes were found to be highly sensitive to the local environment, and the probes are oriented nearly parallel with the membrane normal. Slow binding kinetics and scattering in absorption spectra indicate, especially for di-8-ANEPPS, involvement of aggregation. On the basis of the experimental spectra and time-dependent density functional theory calculations, we find that aggregate formation may contribute to the blue-shifts seen for the dyes in decanol and when bound to membrane models. In conclusion, solvatochromic and other intermolecular interactions effects also need to be included when considering electrochromic response voltage-sensitive dyes.

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Section: Discussionsupporting

confidence: 90%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Spectral Properties and Orientation of Voltage-Sensitive Dyes in Lipid Membranes

et al. 2012

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“…It corresponds to incorporating a finite line-width for the optical transition, which extends the validity of the TSA in near resonance regimes. A damping factor γ of 0.2 eV has been chosen, which is consistent with the half width at half-maximum of the absorption band of di-8-ANEPPS as measured in solution Figure presents a typical time evolution of the β HRS ∞ , β HRS 1064nm , and β HRS 1064nm–0.2 quantities, respectively, here for the ANEPPS@POPC system, as well as their cumulative averages.…”

Section: Resultsmentioning

confidence: 99%

“…A damping factor γ of 0.2 eV has been chosen, which is consistent with the half width at half-maximum of the absorption band of di-8-ANEPPS as measured in solution. 153 , and β HRS 1064nm−0.2 quantities, respectively, here for the ANEPPS@POPC system, as well as their cumulative averages. For the static case, even though individual values vary over time, the cumulative average rapidly converges.…”

Section: Resultsmentioning

confidence: 99%

Unravelling the Effects of Cholesterol on the Second-Order Nonlinear Optical Responses of Di-8-ANEPPS Dye Embedded in Phosphatidylcholine Lipid Bilayers

2021

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Cholesterol is known for its role in maintaining the correct fluidity and rigidity of the animals cell membranes and thus their functions. Assessing the content and the role of cholesterol in lipid bilayers is therefore of crucial importance for a deeper understanding and control of membrane functioning. In this computational work, we investigate bilayers built from three types of glycerophospholipid phosphatidylcholine (PC) lipids, namely dipalmitoylphosphatidylcholine (DPPC), 1-palmitoyl-2-oleoyl-snglycero-3-phosphocholine (POPC), and dioleoylphosphatidylcholine (DOPC), and containing different amounts of cholesterol by analyzing the second-harmonic generation (SHG) nonlinear optical (NLO) response of a probe molecule, di-8-ANEPPS, inserted into the membranes. This molecular property presents the advantage to be specific to interfacial regions such as lipid bilayers. To unravel these effects, Molecular Dynamics (MD) simulations have been performed on both DPPC and DOPC lipids by varying the cholesterol mole fraction (from 0 to 0.66), while POPC was only considered as a pure bilayer. In the case of the structural properties of the bilayers, all the analyses converge toward the same conclusion: as the mole fraction of cholesterol increases, the systems become more rigid, confirming the condensing effect of cholesterol. In addition, the chromophore is progressively more aligned with respect to the normal to the bilayer. On the contrary, addition of unsaturation disorders the lipid bilayers, with barely no impact on the alignment of the chromophore. Then, using the frames obtained from the MD simulations, the first hyperpolarizability β of the dye in its environment has been computed at the TDDFT level. On the one hand, the addition of cholesterol induces a progressive increase of the diagonal component the β tensor parallel to the bilayer normal. On the other hand, larger β values have been calculated for the unsaturated than for the saturated lipid systems. In summary, this study illustrates the relationship between the composition and structure of the bilayers and the NLO responses of the embedded dye.

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Positional isomers of heterocyclic azo dyes: Investigation of NLO properties by Z-scan and correlative DFT studies

Ghanavatkar

Mishra

Ayare

et al. 2021

Journal of the Indian Chemical Society

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Solvent effects on the nonlinear optical response of a potentiometric biological imaging dye

Cited by 11 publications

References 39 publications

Spectral Properties and Orientation of Voltage-Sensitive Dyes in Lipid Membranes

Spectral Properties and Orientation of Voltage-Sensitive Dyes in Lipid Membranes

Unravelling the Effects of Cholesterol on the Second-Order Nonlinear Optical Responses of Di-8-ANEPPS Dye Embedded in Phosphatidylcholine Lipid Bilayers

Positional isomers of heterocyclic azo dyes: Investigation of NLO properties by Z-scan and correlative DFT studies

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