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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Kononenko, Denys |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Muller, Hermance |
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Kočí, Jan | Prague |
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Šuljagić, Marija |
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Kalteremidou, Kalliopi-Artemi | Brussels |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Santos, Lmnbf
in Cooperation with on an Cooperation-Score of 37%
Topics
Publications (23/23 displayed)
- 2023Confined Silver Nanoparticles in Ionic Liquid Filmscitations
- 2022Ohmic heating-assisted synthesis and characterization of Zn(ii), Cu(ii) and Pd(ii) complexes of heterocyclic-fused chlorinscitations
- 2022The impact of the cation alkyl chain length on the wettability of alkylimidazolium-based ionic liquids at the nanoscalecitations
- 2022Extensive characterization of choline chloride and its solid-liquid equilibrium with watercitations
- 2022Enthalpy of solvation of alkali metal salts in a protic ionic liquid: Effect of cation charge and sizecitations
- 2022Solid-Liquid-Gas Phase Equilibria for Small Phenylene-Thiophene Co-Oligomerscitations
- 2022The effect of oxidation state and tert-butyl substituents on the thermal behavior and thin-film morphology of cobalt-complexes (FK 102 and FK 209)citations
- 2021On the Aromatic Stabilization of Fused Polycyclic Aromatic Hydrocarbonscitations
- 2020Morphology, Structure, and Dynamics of Pentacene Thin Films and Their Nanocomposites with [C(2)C(1)im][NTf2] and [C(2)C(1)im][OTF] Ionic Liquidscitations
- 2019Synthesis of Pyridyl and N-Methylpyridinium Analogues of Rosamines: Relevance of Solvent and Charge on Their Photophysical Propertiescitations
- 2019Oxidative Treatment of Multi-Walled Carbon Nanotubes and its Effect on the Mechanical and Electrical Properties of Green Epoxy based Nano-Compositescitations
- 2018High purity and crystalline thin films of methylammonium lead iodide perovskites by a vapor deposition approachcitations
- 2018Thin film deposition of organic hole transporting materials: optical, thermodynamic and morphological properties of naphthyl-substituted benzidinescitations
- 2018Nucleation and growth of microdroplets of ionic liquids deposited by physical vapor method onto different surfacescitations
- 2017On the Deposition of Lead Halide Perovskite Precursors by Physical Vapor Methodcitations
- 2016Morphology of Imidazolium-Based Ionic Liquids as Deposited by Vapor Deposition: Micro-/Nanodroplets and Thin Filmscitations
- 2016The effect of n vs. iso isomerization on the thermophysical properties of aromatic and non-aromatic ionic liquidscitations
- 2015Description and Test of a New Multilayer Thin Film Vapor Deposition Apparatus for Organic Semiconductor Materialscitations
- 2007Thermochemical studies of five crystalline bis(O-alkyl-N-thenoylthiocarbamato)nickel(II) complexescitations
- 2004Standard molar enthalpies of formation of two crystalline bis[N-(diethylaminothiocarbonyl)benzamidinato]nickel(II) complexescitations
- 2004Standard molar enthalpies of formation of two crystalline bis[N-(diethylaminothiocarbonyl)benzamidinato]nickel(II) complexescitations
- 2004Thermodynamics of the interaction between a hydrophobically modified polyelectrolyte and sodium dodecyl sulfate in aqueous solutioncitations
- 2004Thermochemical studies of three bis(O-alkyl-N-benzoylthiocarbamato)nickel(II) complexescitations
Places of action
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article
Synthesis of Pyridyl and N-Methylpyridinium Analogues of Rosamines: Relevance of Solvent and Charge on Their Photophysical Properties
Abstract
A series of pyridyl analogues of rosamines was prepared by employing two methodologies: (i) the conventional-heating condensation of a pyridinecarboxaldehyde with 3-(diethylamino)phenol in propionic acid, and (ii) the novel ohmic-heating assisted condensation under "on water" conditions, followed by oxidation. The 4-pyridyl substituted rosamine was further converted into the N-methylpyridinium derivative through N-alkylation using methyl iodide. The influence of the position and cationization of the nitrogen atom of the pyridyl ring in the physicochemical properties of fluorophores was investigated by H-1, C-13, N-15 NMR spectral analysis, UV/Vis and fluorescence spectroscopy, single-crystal X-ray diffraction (4-pyridyl and N-methylpyridinium derivatives) and thermal-behavior analysis. Curiously, for ethanolic solutions of 4-pyridyl and N-methylpyridinium derivatives an extinction of color and fluorescence over time was observed. This phenomenon was further studied and the data revealed that it is the result of nucleophilic addition of ethoxide ion to the central 9-position of the xanthene. The kinetics of the process is slower for the 4-pyridyl rosamine, which emphasizes the importance of the charge in the N-methylpyridinium analogue in the reactivity of the molecule towards a nucleophile agent. This phenomenon is reversible, meaning that the compounds can be rapidly recovered by decreasing the pH, opening new avenues in the sensing applications of this class of rosamines.