On the Estimation of Excited-State Dipole Moments from Solvatochromic Shifts of Absorption and Fluorescence Spectra

Kawski, A.

doi:10.1515/zna-2002-0509

Cited by 253 publications

(109 citation statements)

References 17 publications

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“…The blue S 2 fluorescence of 247 in solution is essentially invariant to solvent polarity, but the NIR fluorescence seen in a nonpolar environment red shifts and becomes quenched as the polarity increases (Table S1) (19,20). Thus, 247 is a "sensitive fluorophore" (21) whose NIR emission color and intensity provides insight into its microenvironment within a biological system.…”

Section: Resultsmentioning

confidence: 99%

Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation

Trivedi

Harney

Olive

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

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A chiral porphyrazine (pz), H 2 [pz( trans - A 2 B 2 )] (247), has been prepared that exhibits preferential in vivo accumulation in the cells of tumors. Pz 247 exhibits near-infrared (NIR) emission with λ > 700 nm in the required wavelength range for maximum tissue penetration. When MDA-MB-231 breast tumor cells are treated with 247, the agent shows strong intracellular fluorescence with an emission maximum, 704 nm, which indicates that it localizes within a hydrophobic microenvironment. Pz 247 is shown to associate with the lipophilic core of LDL and undergo cellular entry primarily through receptor-mediated endocytosis accumulating in lysosomes. Preliminary in vivo studies show that 247 exhibits preferential accumulation and retention in the cells of MDA-MB-231 tumors subcutaneously implanted in mice, thereby enabling NIR optical imaging with excellent contrast between tumor and surrounding tissue. The intensity of fluorescence from 247 within the tumor increases over time up to 48 h after injection presumably due to the sequestration of circulating 247/LDL complex by the tumor tissue. As the need for cholesterol, and thus LDL, is elevated in highly proliferative tumor cells over nontumorigenic cells, 247 has potential application for all such tumors.

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Section: Resultsmentioning

confidence: 99%

Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation

Trivedi

Harney

Olive

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

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“…These equations are obtained by considering the solute polarizability ( α ) to be isotropic and the condition 2 α / a 3 = 1 . Here, ‘ a ’ refers to the solute Onsager cavity radius, and furthermore, n and ε are the refractive index and solvent dielectric constant, respectively.…”

Section: Theoretical Backgroundmentioning

confidence: 99%

Solvatochromic study of 3‐N‐(N′‐methylacetamidino)benzanthrone and its interaction with dopamine by the fluorescence quenching mechanism

Bharathi¹,

Siddlingeshwar²,

Shivraj³

et al. 2018

Luminescence

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The change in photophysical properties of the organic molecule due to solvatochromic effect caused by different solvent environments at room temperature gives information about the dipole moments of 3-N-(N'-methylacetamidino)benzanthrone (3-MAB). The quantum yield, fluorescence lifetime of 3-MAB was measured in different solvents to calculate radiative and non-radiative rate constants. The results revealed that the excited state dipole moment (μ ) is relatively larger compared to the ground state dipole moment (μ ), indicating the excited state of the dye under study is more polar than the ground state and the same trend is noticed with theoretical calculations performed using the CAM-B3LYP/6-311+G(d,p) method. Further, the study on preferential solvation was carried out for 3-MAB dye in ethyl acetate-methanol solvent mixture. The fluorescence quenching method has been employed for the detection of dopamine using 3-MAB as fluorescent probe, using steady-state and time resolved methods at room temperature. The method enables dopamine in the micro molar range to be detected. Also, an attempt to verify the quenching process by employing different models has been tried. Various rate parameters are measured using these models, our results indicates the quenching process is diffusion limited.

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“…Among the techniques available for elucidation of the ground and excited state dipole moments, the most accepted technique is based on Bilot-Kawski equation and Bakhshiev [58]. This solvatochromic method is based on the shifts in the absorption and emission maxima with polarity functions of solvents, expressed by the dielectric constant (ε) and refractive index (n) of the solvent medium.…”

Section: Dipole Moment Ratio Calculation Using Solvatochromic and Dftmentioning

confidence: 99%

“…The μ g and μ e values of a molecule can be determined by the solvent-polarity dependences of the absorption and fluorescence spectra on the basis of the simple quantummechanical second-order perturbation theory by BilotKawski et al by using the following solvent polarity parameters, f BK (ε, n)and g BK (ε, n) [45,58,59].…”

Section: Dipole Moment Ratio Calculation Using Solvatochromic and Dftmentioning

confidence: 99%

AIE Based Coumarin Chromophore - Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters

Lanke

Sekar

2015

J Fluoresc

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A new class of red emitting extensively conjugated donor-π-acceptor type dyes bearing coumarin units have been synthesized by condensation of 7-(diethylamino)-2-oxo-2 H-chromene-3-carbaldehyde with different active methylenes. All the dyes are characterized by (1)H NMR, (13)C NMR and HRMS spectroscopy. The photophysical behaviour and the relation between structure and properties of the coumarin "push-pull" derivatives were investigated experimentally. The dyes exhibited positive solvatochromism and solvatofluorism in solution of varying polarity. These coumarin dyes show aggregation induced emission properties with red emitting fluorescence. They show absorption in the range of 501-528 and emission in the range of 547-630 nm. We evaluated photophysical properties of coumarin dyes using solvotochromism and solvent dependent shift in the emission wavelength. All the synthesized coumarin dyes COS1-COS4 are showing very good solvatochromic properties.

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On the Estimation of Excited-State Dipole Moments from Solvatochromic Shifts of Absorption and Fluorescence Spectra

Cited by 253 publications

References 17 publications

Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation

Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation

Solvatochromic study of 3‐N‐(N′‐methylacetamidino)benzanthrone and its interaction with dopamine by the fluorescence quenching mechanism

AIE Based Coumarin Chromophore - Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters

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