Photoacids as singlet oxygen photosensitizers: Direct determination of the excited state acidity by time-resolved spectroscopy

Alazaly, Ahmed M.M.; Amer, Aya S.I.; Fathi, Ahlam M.; Abdel-Shafi, Ayman A.

doi:10.1016/j.jphotochem.2018.07.019

Cited by 11 publications

(3 citation statements)

References 48 publications

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“…5. In contrast to our previous observation [2,[6][7][8][9][10] that the dependence of  on E T N always presented two groups of solvents one for protic and other for aprotic solvents, the current set of compounds show linear dependence for 1NA4S and 2NA6S on E T N as shown in Fig. 5.…”

Section: Resultscontrasting

confidence: 99%

“…ICT compounds are characterized by the existence of an electron-donating and electron withdrawing moieties linked by -bridge (D--A). Research interests in ICT systems are also extended for the study of molecular systems having an intermolecular charge transfer excited state but greatly influenced by specific interactions [2][3][4][5][6][7][8][9][10]. For molecular systems with excited state intramolecular charge transfer (ESICT) phenomenon, in most cases the observed dual emission arises from the locally (LE) and intramolecular charge transfer (ICT) states.…”

Section: Introductionmentioning

confidence: 99%

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Solvent Effect on the Excited Charge Transfer State of Naphthylamine Sulfonate Derivatives: Steady State and Time resolved studies

et al. 2022

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Solvent effect on the absorption and fluorescence emission spectra of 1-naphthylamine-4-sulfonate (1NA4S) and 2naphthylamine-6-sulfonate (2NA6S) were investigated. Excited state fluorescence decay measurements were also measured in different solvents. The spectral shifts are well correlated with several multiparametric relationships that predict the participation hydrogen bonding interactions (specific) versus non-hydrogen bonding interactions (non-specific) on the photophysical properties. Kamlet-Taft with their three parametric relationship which was then improved by Catalán by splitting the * (dipolarity/polarizability) to parameters namely, solvent"s polarizability) solvent"s dipolarity, and very recently Laurence relationships. The three-parameter relationship by Kamlet-Taft has shown that the absorption energy is mainly controlled by specific interactions while the emission energy is controlled by the non-specific interactions. On the other hand, Catalán"s treatment has shown that non-specific interaction has higher contribution to the emission energy than predicted by Kamlet-Taft treatment. Laurence"s treatment has shown that hydrogen bonding interaction has higher contribution than non-hydrogen bonding interactions to the emission energy for both compounds while they contribute equally to their absorption energy.

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Section: Resultscontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solvent Effect on the Excited Charge Transfer State of Naphthylamine Sulfonate Derivatives: Steady State and Time resolved studies

et al. 2022

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“…Thus, they have a variety of applications in catalytic synthesis, biological processes, and other experiments involving pH-jump. 1–5 Using naphthols, 6–10 hydroxypyrenes 11–14 and their cyano, 15–22 sulfonyl 21,23 and sulfonate 12,24,25 derivatives, the excited state acidity and proton transfer (ESPT) kinetics of ArOHs in their excited singlet state have been extensively studied. 16,26 The in an aqueous solution typically ranges from −8.5 to 3.4, and the ESPT rate constant ( k PT ) scales with acidity.…”

Section: Introductionmentioning

confidence: 99%

Excited state proton transfer of triplet state p-nitrophenylphenol to amine and alcohol: a spectroscopic and kinetic study

Pan

Han

Long

et al. 2022

Phys. Chem. Chem. Phys.

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Fluorimetric Cell Analysis with 9‐Aryl‐Substituted Berberine Derivatives as DNA‐Targeting Fluorescent Probes

Groß,

Hoffmann,

Müller

et al. 2023

ChemBioChem

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DNA‐sensitive fluorescent light‐up probes based on berberine are presented. This biogenic fluorophore was chosen as central unit to use its potential biocompatibility and its DNA‐binding properties. To provide predictable fluorescence quenching in aqueous solution and a fluorescence light‐up effect upon DNA binding, aryl substituents were attached at the 9‐position by Suzuki‐Miyaura coupling reactions. The 9‐arylberberine derivatives have a very low fluorescence quantum yield (Φfl=<0.02), which is caused by the radiationless deactivation of the excited state by torsional relaxation about the biaryl axis. In addition, these berberine derivatives intercalate into DNA with high affinity (Kb=2.0−22×104 M−1). Except for the nitrophenyl‐ and hydroxyphenyl‐substituted derivatives, all tested compounds exhibited a pronounced fluorescence light‐up effect upon association with DNA, because the deactivation of the excited‐state by torsional relaxation is suppressed in the DNA binding site. Most notably, it was shown exemplarily with the 9‐(4‐methoxyphenyl)‐ and the 9‐(6‐methoxynaphthyl)‐substituted derivatives that these properties are suited for fluorimetric cell analysis. In particular, these probes generated distinct staining patterns in eukaryotic cells (NIH 3T3 mouse fibroblasts), which enabled the identification of nuclear substructures, most likely heterochromatin or nucleoli, respectively.

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Photoacids as singlet oxygen photosensitizers: Direct determination of the excited state acidity by time-resolved spectroscopy

Cited by 11 publications

References 48 publications

Solvent Effect on the Excited Charge Transfer State of Naphthylamine Sulfonate Derivatives: Steady State and Time resolved studies

Solvent Effect on the Excited Charge Transfer State of Naphthylamine Sulfonate Derivatives: Steady State and Time resolved studies

Excited state proton transfer of triplet state p-nitrophenylphenol to amine and alcohol: a spectroscopic and kinetic study

Fluorimetric Cell Analysis with 9‐Aryl‐Substituted Berberine Derivatives as DNA‐Targeting Fluorescent Probes

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