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Projeto de investigação
Selective Fluorescent Chemosensors and Functionalized Materials for Lithium Detection
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A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
Publication . Gomes, Liliana J.; Carrilho, João P.; Pereira, Pedro M.; Moro, Artur J.; DQ - Departamento de Química; LAQV@REQUIMTE; Instituto de Tecnologia Química e Biológica António Xavier (ITQB); MDPI - Multidisciplinary Digital Publishing Institute
A new Near InfraRed (NIR) fluorescent chemosensor for metal ions and anions is herein presented. The fluorophore is based on a styrylflavylium dye, a synthetic analogue of the natural anthocyanin family, with a di-(2-picolyl)amine (DPA) moiety as the metal chelating unit. The substitution pattern of the styrylflavylium core (with tertiary amines on positions 7 and 4′) shifts the optical properties of the dye towards the NIR region of the electronic spectra, due to a strong push-pull character over the π-conjugated system. The NIR chemosensor is highly sensitive to the presence of Zn2+, which induces a strong CHelation Enhanced Fluorescence (CHEF) effect upon binding to the DPA unit (2.7 fold increase). The strongest competing ion is Cu2+, with a complete fluorescence quenching, while other metals induce lower responses on the optical properties of the chemosensor. Subsequent anion screening of the Zn2+-chemosensor coordination compound has demonstrated a distinct selectivity towards adenosine 5′-triphosphate (ATP) and adenosine 5′-diphosphate (ADP), with high association constants (K ~ 106 M−1) and a strong CHEF effect (2.4 and 2.9 fold fluorescence increase for ATP and ADP, respectively). Intracellular studies with the Zn2+-complexed sensor showed strong luminescence in the cellular membrane of Gram– bacteria (E. coli) and mitochondrial membrane of mammalian cells (A659), which highlights its possible application for intracellular labelling.
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Fundação para a Ciência e a Tecnologia
Programa de financiamento
OE
Número da atribuição
UI/BD/153617/2022