Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives

Serdiuk, Illia E.; Roshal, Alexander D.

doi:10.1039/c5ra13912k

Cited by 22 publications

(24 citation statements)

References 26 publications

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“…This is achieved by introducing a higher level of complexity into the molecule’s excited-state behavior with adding another proton-donating or proton accepting center to promote concurrent proton transfer pathways, 35,36 or design a molecule with more than one intramolecular hydrogen bond capable of excited-state proton transfer. 37,38 …”

Section: Resultsmentioning

confidence: 99%

“…Multiple efforts have been reported to design and explore the ESIPT molecules with an increased number of independent channels that provide information about their microenvironment. This is achieved by introducing a higher level of complexity into the molecule’s excited-state behavior with adding another proton-donating or proton accepting center to promote concurrent proton transfer pathways, , or design a molecule with more than one intramolecular hydrogen bond capable of excited-state proton transfer. , …”

Section: Resultsmentioning

confidence: 99%

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Ratiometric Fluorescent Sensor Array as a Versatile Tool for Bacterial Pathogen Identification and Analysis

et al. 2018

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Rapid and reliable identification of pathogenic microorganisms is of great importance for human and animal health. Most conventional approaches are time-consuming and require expensive reagents, sophisticated equipment, trained personnel, and special storage and handling conditions. Sensor arrays based on small molecules offer a chemically stable and cost-effective alternative. Here we present a ratiometric fluorescent sensor array based on the derivatives of 2-(4′-N,N-dimethylamino)-3-hydroxyflavone, and investigate its ability to provide a dual-channel ratiometric response. We demonstrate that by using discriminant analysis of the sensor array responses, it is possible to effectively distinguish between eight bacterial species and recognize their Gram status. Thus, multiple parameters can be derived from the same dataset. Moreover, the predictive potential of this sensor array is discussed, and its ability to analyze unknown samples beyond the list of species used for the training matrix is demonstrated. The proposed sensor array and analysis strategies open new avenues for the development of advanced ratiometric sensors for multiparametric analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Ratiometric Fluorescent Sensor Array as a Versatile Tool for Bacterial Pathogen Identification and Analysis

et al. 2018

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“…Synthesis. Following the approach reported previously, 25 1 was synthesized starting from 1-(5-acetyl-2,4-dihydroxyphenyl)-3-phenylpropan-1-one (3), which was condensed with 4-(dimethylamino)benzaldehyde (Claisen−Schmidt condensation) followed by the intramolecular cyclization of the obtained chalcone derivative (4) in the presence of I 2 in hot DMSO (Scheme 1). 2 was prepared from 1 in the reaction with dimethylsulfate in the presence of K 2 CO 3 .…”

Section: ■ Experimental and Theoretical Methodsmentioning

confidence: 99%

“…The 3-phenylpropanoyl fragment was utilized in the role of both proton acceptor for ESIPT and a bulky substituent to afford selective reaction of substrate 3 (Scheme 1) with one equivalent of 4-(dimethylamino)benzaldehyde in the Claisen−Schmidt condensation. 25 Spectral features of compound 1 were investigated by electronic spectroscopy methods in various solvents and polymers and analyzed to gain more knowledge on the reasons affording white fluorescence. Conclusions on the origin of spectral behavior of 1 were drawn with the help of quantum calculations and comparison of spectral features with a related compound (2, Chart 1), containing the methyl-blocked hydroxyl group.…”

Section: ■ Introductionmentioning

confidence: 99%

White Light from a Single Fluorophore: A Strategy Utilizing Excited-State Intramolecular Proton-Transfer Phenomenon and Its Verification

Serdiuk

2017

J. Phys. Chem. C

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This article is devoted to the development of a strategy for the design of a single fluorophore emitting white light due to the excited-state intermolecular proton-transfer (ESIPT) phenomenon. The key parameters of this strategy include (i) selection of an effective blue emitter, (ii) its structural modification to enable ESIPT, and (iii) adjustment of ESIPT parameters to assess similar fluorescence intensities of both emission bands. The important factor which determines similar intensity of these bands was found to be energetic closeness of the species participating in ESIPT (Δ298 G° ESIPT ≈ 0), which makes this phototransformation reversible. Verification of the proposed strategy was carried out by design and synthesis of a new ESIPT fluorophore, which exhibits white light under certain conditions. Spectral features of this compound were investigated in various liquid solutions and solid polymeric films by means of steady-state electronic absorption and steady-state, time-resolved, and temperature-dependent fluorescence spectroscopies. The conclusions on the tautomeric transformations in this compound and the origin of its spectral features are supported by quantum-chemical calculations on the density functional theory (DFT) and time-dependent DFT levels of theory. The results of investigations confirm the hypothesis that white light can be produced by a single fluorophore and evidence the applicability of the proposed strategy.

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“…Based on these results, the theoretical calculation of PTI‐DMSO was closer to the experimental data. [ 60 ] It also showed that the current level of calculation was reasonable and the data was reliable. Otherwise,…”

Section: Resultsmentioning

confidence: 90%

Sensing Mechanism of Excited‐State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide

et al. 2021

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Density-functional-theory/Time-dependent density-functional-theory | Hydrogen bonds | Fluorescent probes | Electron transfer | Dimethyl sulfoxide Excited-state hydrogen bond strongly affects the intramolecular charge conversion process, which is very suitable for the design and development of high-performance fluorescent probes. However, as one of the most common solvents or additives used in sensing, the role of dimethyl sulfoxide (DMSO) in the system of the excited-state hydrogen bond is seldom explored. As the goal of this research, we investigated the sensing mechanism of a CORM3-green fluorescent probe system for carbon monoxide releasing molecule (CORM-3) detection and tracking in vivo, through quantum chemistry calculations based on density-functional-theory (DFT)/ time-dependent density-functional-theory (TDDFT) methods. Based on the analysis of the solvent effect of DMSO by the reduced density gradient function and IR spectroscopy, we provided a new strategy to explain the fluorescence mechanism. Subsequently, we verified the result through the potential energy curve of Phthalimide (PTI, the reduced product of CORM3-green). The excited-state hydrogen bond between PTI and DMSO promotes radiation transition and leads to obvious difference in the photophysical properties of PTI and PTI-DMSO.

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Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives

Abstract: 3,7-Dihydroxyflavone derivatives containing carbonyl fragments were synthesized. Results of the fluorescent spectroscopy investigations indicate that one of them undergoes Excited State Intramolecular Double Proton Transfer (ESIDPT).

Cited by 22 publications

References 26 publications

Ratiometric Fluorescent Sensor Array as a Versatile Tool for Bacterial Pathogen Identification and Analysis

Ratiometric Fluorescent Sensor Array as a Versatile Tool for Bacterial Pathogen Identification and Analysis

White Light from a Single Fluorophore: A Strategy Utilizing Excited-State Intramolecular Proton-Transfer Phenomenon and Its Verification

Sensing Mechanism of Excited‐State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide

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