Solvatochromism as a new tool to distinguish structurally similar compounds

Madeira, Pedro P.; Loureiro, Joana A.; Freire, Mara G.; Coutinho, João A. P.

doi:10.1016/j.molliq.2018.11.050

Cited by 10 publications

(5 citation statements)

References 32 publications

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“…CsCl is a common inhibitor of potassium channels since the radius of Cs + is significantly bigger than that of K + . Since Rb and Cesium (Cs) belong to the same main group, they are considered to have some similar physicochemical and biological properties [27]. However, the regulatory effects of Rb on cell response and bacteria multiplication have been rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Rubidium doped nano-hydroxyapatite with cytocompatibility and antibacterial

Liu

Tan

2020

Journal of Asian Ceramic Societies

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Section: Introductionmentioning

confidence: 99%

Rubidium doped nano-hydroxyapatite with cytocompatibility and antibacterial

Liu

Tan

2020

Journal of Asian Ceramic Societies

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“…All calculations have been performed for the tautomeric transitions of the quercetin molecule as their intrinsic property, that is adequate for modeling of the processes occurring in real systems [101–106].…”

Section: Methodsmentioning

confidence: 99%

Intramolecular tautomerization of the quercetin molecule due to the proton transfer: QM computational study

Brovarets’¹,

Hovorun²

2019

PLoS ONE

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Quercetin molecule (3, 3′, 4′, 5, 7-pentahydroxyflavone, C15H10O7) is an important flavonoid compound of natural origin, consisting of two aromatic A and B rings linked through the C ring with endocyclic oxygen atom and five hydroxyl groups attached to the 3, 3′, 4′, 5 and 7 positions. This molecule is found in many foods and plants, and is known to have a wide range of therapeutic properties, like an anti-oxidant, anti-toxic, anti-inflammatory etc. In this study for the first time we have revealed and investigated the pathways of the tautomeric transformations for the most stable conformers of the isolated quercetin molecule (Brovarets’ & Hovorun, 2019) via the intramolecular proton transfer. Energetic, structural, dynamical and polar characteristics of these transitions, in particular relative Gibbs free and electronic energies, characteristics of the intramolecular specific interactions–H-bonds and attractive van der Waals contacts, have been analysed in details. It was demonstrated that the most probable process among all investigated is the proton transfer from the O3H hydroxyl group of the C ring to the C2′ carbon atom of the C2′H group of the B ring along the intramolecular O3H…C2′ H-bond with the further formation of the C2′H2 group. It was established that the proton transfer from the hydroxyl groups to the carbon atoms of the neighboring CH groups is assisted at the transition states by the strong intramolecular HCH…O H-bond (~28.5 kcal∙mol-1). The least probable path of the proton transfer–from the C8H group to the endocyclic O1 oxygen atom–causes the decyclization of the C ring in some cases. It is shortly discussed the biological importance of the obtained results.

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“…The colorimetric changes can be measured by UV-vis spectroscopy, where the position, intensity, and shape of the spectra depend on the nature of the solvent [2]. The in uence of solvents on the optical properties of organic compounds, organometallic, metal-organic frameworks, and metal complexes has been studied for a long time [3]. The solvation behavior plays a signi cant role in the colorimetric properties of these systems, which depend on the intermolecular forces between the solvent and solute.…”

Section: Introductionmentioning

confidence: 99%

Solvatochromism of a silver-epoxy nanocomposite dispersed in organic solvents

Sánchez

Barrera-Calva

Rentería-Tapia

2022

Preprint

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Fresh and aged silver-epoxy nanocomposites were dispersed in aprotic solvents having different dielectric constants (ε) like Acetone (Ace), N, N-dimethylformamide (DMF), and dimethylsulphoxide (DMSO). Different colors and hues of the dispersions depending on the dielectric constant of the solvents were observed, suggesting a solvatochromic behavior. Aggregated and isolated triangular silver nanoprisms with sharp corners were predominant for fresh and aged dispersions in Acetone (ε = 21.0), respectively. Whereas, aggregated and isolated truncated triangular silver nanoprisms were observed for the ones in DMF (ε = 36.7), respectively. Stacks of elongated silver nanoparticles (Nps) predominated for both fresh and aged dispersions prepared in DMSO (ε = 47.2). It was found that as the dielectric constant of the solvents increases the average size of the Nps diminishes and the silver nanoprisms were transformed into elongated shapes, for both fresh and aged samples. These morphologies have an important impact on the position and shape of the plasmonic resonance. The dipolar optical extinction maximum of the silver Nps of aged samples was linearly red-shifted with an increase in the dielectric constant of the solvents. On the other hand, it was observed higher stability for silver Nps dispersed in DMSO and DMF compared with Ace in both fresh and aged samples. The results show the influence of the solvent dielectric constant on the optical properties, size distribution, morphology, and stability of the silver Nps. A solvatochromic mechanism of the silver Nps based on the coalescence of small silver seed Nps (< 40 nm) is proposed.

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Solvatochromism as a new tool to distinguish structurally similar compounds

Cited by 10 publications

References 32 publications

Rubidium doped nano-hydroxyapatite with cytocompatibility and antibacterial

Rubidium doped nano-hydroxyapatite with cytocompatibility and antibacterial

Intramolecular tautomerization of the quercetin molecule due to the proton transfer: QM computational study

Solvatochromism of a silver-epoxy nanocomposite dispersed in organic solvents

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