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However, despite their remarkable potential, reports on organometallic dyes bearing NIs are scarce and virtually inexistent regarding palladium(II) complexes. Herein, we report the synthesis of NIs bearing phosphine and amine chelating moieties and the characterization of their optical properties both as single molecules and when complexed on Pd(II) ions. It is shown that the introduction of phosphine moieties in the naphthalimide core results in a marked increase in non\u2010radiative processes, leading to a significant reduction of the emission efficiency and lifetime of these dyes, compared to amine\u2010bearing counterparts. The complexation to Pd(II) sequesters the electronic contribution of chelating moieties, with complexes assuming an optical behavior similar to that of unsubstituted 1,8\u2010naphthalimide. The complexation significantly increases the acidity of chelating secondary amines, giving rise to an unexpected intramolecular reaction that results in the formation of a novel 1,8\u2010naphthalimide dye bearing a cyclic phosphorylamide moiety. The new dye exhibits good emission quantum yield, long fluorescence lifetime and sensitivity to basic media, evidencing potential for application in optical imaging and sensing scenarios.<\/jats:p>","DOI":"10.1002\/chem.202301597","type":"journal-article","created":{"date-parts":[[2023,6,28]],"date-time":"2023-06-28T07:23:13Z","timestamp":1687936993000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Naphthalimide\u2010Dyes Bearing Phosphine and Phosphorylamide Moieties: Synthesis and Optical Properties"],"prefix":"10.1002","volume":"29","author":[{"given":"Massimo","family":"Tosolini","sequence":"first","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences University of Trieste  via Giorgieri 1 34127 Trieste Italy"}]},{"given":"Chiara","family":"Alberoni","sequence":"additional","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences University of Trieste  via Giorgieri 1 34127 Trieste Italy"}]},{"given":"Mani","family":"Outis","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry NOVA School of Science and Technology Universidade NOVA de Lisboa, Campus da Caparica  2829-516 Caparica Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1333-9076","authenticated-orcid":false,"given":"Ant\u00f3nio Jorge","family":"Parola","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry NOVA School of Science and Technology Universidade NOVA de Lisboa, Campus da Caparica  2829-516 Caparica Portugal"}]},{"given":"Barbara","family":"Milani","sequence":"additional","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences University of Trieste  via Giorgieri 1 34127 Trieste Italy"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0088-1077","authenticated-orcid":false,"given":"Paolo","family":"Tecilla","sequence":"additional","affiliation":[{"name":"Department of Chemical and Pharmaceutical 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