Radiationless deactivation of 6-aminocoumarin from the S1-ICT state in nonspecifically interacting solvents

Krystkowiak, Ewa; Dobek, Krzysztof; Burdziński, Gotard; Maciejewski, Andrzej

doi:10.1039/c2pp25065a

Cited by 27 publications

(55 citation statements)

References 54 publications

(99 reference statements)

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“…Both effects can be attributed to the increase of the polarity of the solvent induced by adding more polar water to less polar ethanol. It has been already demonstrated for various coumarins that increasing solvent polarity results in a red‐shift of the fluorescence spectrum and increase of the fluorescence lifetime . We note that at 27.7 mM concentration in 99.8% ethanol the dye is already strongly aggregated thus we do not expect a significant increase of the aggregation degree due to the increased water content.…”

Section: Resultssupporting

confidence: 45%

Two‐photon excited lasing of Coumarin 307 for lysozyme amyloid fibrils detection

Hańczyc

Procyk

Radzewicz

et al. 2019

Journal of Biophotonics

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Amyloid fibrils are a well‐recognized hallmark of neurodegeneration. A common approach to detect amyloid fibrils is staining with organic molecules and monitoring optical properties using fluorescence spectroscopy. However, the structural diversity of amyloids necessitates new sensitive methods and probes that can be reliably used to characterize them. Here, Coumarin 307 is applied for lysozyme fibrils detection by observation of laser action in the process of two‐photon excited stimulated emission. It is shown that the lasing threshold and spectrum significantly depend on the adopted structure (α‐helix or β‐sheet) of the lysozyme protein, whereas fluorescence spectrum is insensitive to the protein structure. The applications of coherent stimulated emission light that can be emitted deep inside a scattering medium can be particularly promising for imaging and therapeutic purposes in the neurodegeneration field. Two‐photon excitation with the near‐infrared light, which allows the deepest penetration of tissues, is an important advantage of the method.

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Section: Resultssupporting

confidence: 45%

Two‐photon excited lasing of Coumarin 307 for lysozyme amyloid fibrils detection

Hańczyc

Procyk

Radzewicz

et al. 2019

Journal of Biophotonics

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“…Recently, Krystkowiak et al . reported a detailed study on 6‐aminocoumarin with nonspecifically interacting solvents.…”

Section: Resultsmentioning

confidence: 99%

“…The Kamlet–Taft hydrogen bond donating and accepting abilities are zero ( α = 0, β = 0) in case of nonpolar solvents and due to the lack of π ‐electron they are unable to possess charge transfer character . As a result, their high‐order interactions, i.e .…”

Section: Resultsmentioning

confidence: 99%

“…Similar type of observation also found in 6‐aminocoumarin (6‐AC), C120 and C151 reported by Krystkowiak et al . in nonspecific interacting solvents. From this observation it may indicate that the influence of solvent polarity function in case of nonpolar solvents is very small and the absorption reflects from S 0 and S 1 ‐LE excited states.…”

Section: Resultsmentioning

confidence: 99%

“…We may assume that the absorption spectra of our studied molecule reflect from S 0 ground state (S rel 0 ) to the Franck-Condon locally excited state S 1 (S FC 1 -LE), as like 7-aminocoumarin (12,13). Recently, Krystkowiak et al (28) reported a detailed study on 6-aminocoumarin with nonspecifically interacting solvents.…”

Section: Steady-state Absorption Studymentioning

confidence: 95%

See 2 more Smart Citations

Photophysics of a Coumarin in Different Solvents: Use of Different Solvatochromic Models

Maity

Chatterjee

Seth

2014

Photochem & Photobiology

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This study reported the photophysics of 7-(diethylamino)coumarin-3-carboxylic acid N-succinimidyl ester (7-DCCAE) in different neat solvents of varying polarity using steady-state absorption, fluorescence emission and picosecond time-resolved spectroscopy. In nonpolar solvents, the dye molecule predominantly exists in nonpolar structure and exhibits very low value of nonradiative decay rate constant (k(nr)), demonstrating the emission takes place from S(1) -LE to S(0) ground state. The fluorescence quantum yields, lifetime values of 7-DCCAE in different solvents are rationalized on the basis of intramolecular charge transfer (ICT) followed by twisted intramolecular charge transfer state formation (TICT) as well as specific solute-solvent interactions. Several solvatochromic models (such as Lippert, Dimroth, Kamlet-Taft, Catalán 3P and Catalán 4P models) were used to analyze the solvatochromic shift of 7-DCCAE in different solvents. The different empirical models show that the observed results are better correlate for nonchlorinated solvents and provide statistically significant best-fit result. A comparison was done between comparatively new solvatochromic model (Catalán 3P and Catalán 4P model) with Kamlet-Taft model. The ground state structure of the said molecule was optimized by using Density Functional Theory (DFT).

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Building Molecular Complexity from Quinizarin: Conjoined Coumarins and Coronene Analogs

Węcławski

Deperasińska

Banasiewicz

et al. 2018

Chemistry An Asian Journal

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The double Knoevenagel condensation of 1,4-dibenzoyloxyanthraquinone with methyl esters of arylacetic acids affords a series of compounds based upon a previously unknown 1,8-dioxa-benzo[e]pyrene-2,7-dione heterocyclic core. The aryl groups incorporated in the 3- and 6-positions can be oxidatively coupled to the π-expanded backbone to produce a further new heterocyclic core: 1,10-dioxa-dibenzo[dj]coronene-2,9-dione. The intriguing optical properties of these π-expanded coumarin derivatives are discussed and rationalized through quantum chemical calculations. The broad absorption bands of 1,8-dioxa-benzo[e]pyrene-2,7-dione-based dyes are attributed to both HOMO-1→LUMO and HOMO→LUMO transitions, which have a similar energy. Weakly coupled electron-donating aryl substituents result in a moderate bathochromic shift of both the absorption and emission by 30-60 nm in toluene. The emissive properties of these compounds are in part determined by the oscillator strength of the main transition, lifetimes of the excited state, and by the energy match of the excited state with a triplet state of a similar energy. The 1,10-dioxa-dibenzo[dj]coronene-2,9-dione displays a much smaller Stokes shift, yet a markedly increased fluorescence quantum yield of 90 % owing to the increased rigidity compared with the 1,8-dioxa-benzo[e]pyrene-2,7-dione core.

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Radiationless deactivation of 6-aminocoumarin from the S1-ICT state in nonspecifically interacting solvents

Cited by 27 publications

References 54 publications

Two‐photon excited lasing of Coumarin 307 for lysozyme amyloid fibrils detection

Two‐photon excited lasing of Coumarin 307 for lysozyme amyloid fibrils detection

Photophysics of a Coumarin in Different Solvents: Use of Different Solvatochromic Models

Building Molecular Complexity from Quinizarin: Conjoined Coumarins and Coronene Analogs

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