Browsing by Author "Trilleras, Jorge"
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Item Methoxyquinolone–Benzothiazole Hybrids as New Aggregation-Induced Emission Luminogens and Efficient Fluorescent Chemosensors for Cyanide Ions(MDPI, 2024) Mutis Ayala, Mario; Trilleras, Jorge; D’Vries, Richard; Macías, Mario A.; Insuasty, Alberto; Abonia, Rodrigo; Quiroga, Jairo; Illicachi, Luis A.; Márquez, Edgar; Insuasty, DanielThis work describes the synthesis and characterization of new quinolone–benzothiazole hybrids, the study of their aggregation-induced emission (AIE) properties, and the use of these systems as efficient fluorescent probes for cyanide ions. These conjugated derivatives are linked through a double bond favoring electronic communication, and together with their planar geometry, can strongly aggregate under solvophobic environments, leading to aggregation and exhibiting significant AIE behavior. The double bond between electroactive units is prone to nucleophilic addition reactions by cyanide ions, selectively, conducive to turning off the fluorescence properties, making this hybrid system an efficient probe for cyanide ions. These studies were theoretically explained using DFT and TD-DFT calculations.Item Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones(American Chemical Society, 2024) Insuasty, Daniel; Mutis, Mario; Trilleras, Jorge; Illicachi, Luis A.; Rodríguez, Juan D.; Ramos Hernández, Andrea; San Juan Vergara, Homero G.; Cadena Cruz, Christian; Mora, José R.; Paz, José L.; Méndez López, Maximiliano; Pérez, Edwin G.; Aliaga, Margarita E.; Valencia, Jhesua; Márquez, EdgarIn this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-π–A-D and D-π–A-π-D type push–pull molecular arrangements were synthesized via a Claisen–Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the α,β-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push–pull effect. Moreover, quenching caused by the population of the TICT state in THF–H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 μM. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.