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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\u2032) shifts the optical properties of the dye towards the NIR region of the electronic spectra, due to a strong push-pull character over the \u03c0-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\u2032-triphosphate (ATP) and adenosine 5\u2032-diphosphate (ADP), with high association constants (K ~ 106 M\u22121) 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\u2013 bacteria (E. coli) and mitochondrial membrane of mammalian cells (A659), which highlights its possible application for intracellular labelling.<\/jats:p>","DOI":"10.3390\/s23010471","type":"journal-article","created":{"date-parts":[[2023,1,2]],"date-time":"2023-01-02T03:50:32Z","timestamp":1672631432000},"page":"471","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4810-2770","authenticated-orcid":false,"given":"Liliana J.","family":"Gomes","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Departamento de Qu\u00edmica, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1305-5679","authenticated-orcid":false,"given":"Jo\u00e3o P.","family":"Carrilho","sequence":"additional","affiliation":[{"name":"Intracelular Microbial Infection Biology, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica Ant\u00f3nio Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1426-9540","authenticated-orcid":false,"given":"Pedro M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Intracelular Microbial Infection Biology, Instituto de Tecnologia Qu\u00edmica e Biol\u00f3gica Ant\u00f3nio Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3285-4919","authenticated-orcid":false,"given":"Artur J.","family":"Moro","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Departamento de Qu\u00edmica, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"7105","DOI":"10.1039\/C7CS00240H","article-title":"Fluorescent chemosensors: The past, present and future","volume":"46","author":"Wu","year":"2017","journal-title":"Chem. 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