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The studied oxygen nucleophiles include aromatic and sterically demanding aliphatic alcohols, along with carboxylic acids and peracids. In general, direct substitution of the chloro\u2010SubPz by oxygen nucleophiles of diverse nature proceeds smoothly, with yields of the isolated alkoxy and carboxy\u2010substituted SubPzs ranging from 49 to 100\u2009%. Conversely, direct substitution with sulphur, carbon and nitrogen nucleophiles do not afford the corresponding substituted SubPzs. In these cases, a stepwise procedure involving an axial triflate\u2010SubPz intermediate was employed, affording only the phenyl\u2010SubPz in 8\u2009% yield. The major compound under these conditions was the unreported SubPz \u03bc\u2010oxo dimer, presumably arising from substitution of the triflate\u2010SubPz by the <jats:italic>in\u2005situ<\/jats:italic> generated hydroxy\u2010SubPz. This result indicates a quite low reactivity of the TfO\u2010SubPz intermediate with carbon, sulphur and nitrogen nucleophiles. All SubPzs prepared in this work exhibited fluorescence at 510\u2013515\u2005nm with quantum yields ranging from 0.1 to 0.24. Additionally, all SubPzs generated singlet oxygen, with \u03a6<jats:sub>\u0394<\/jats:sub> values ranging from 0.15 to 0.57, which show no apparent correlation with the axial substituents.<\/jats:p>","DOI":"10.1002\/cplu.202300779","type":"journal-article","created":{"date-parts":[[2024,2,7]],"date-time":"2024-02-07T05:27:15Z","timestamp":1707283635000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Tuning Fluorescence and Singlet Oxygen Quantum Yields of Subporphyrazines by Axial Functionalization"],"prefix":"10.1002","volume":"89","author":[{"given":"Sophia","family":"Ben Ahmed","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-1364-8989","authenticated-orcid":false,"given":"Gema","family":"P\u00e9rez de Bustos","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1848-1167","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Pina","sequence":"additional","affiliation":[{"name":"University of Coimbra CQC-IMS Department of Chemistry  Rua Larga 3004-535 Coimbra Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9335-6935","authenticated-orcid":false,"given":"Tom\u00e1s","family":"Torres","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"},{"name":"Institute for Advanced Research in Chemical Sciences (IAdChem) Universidad Aut\u00f3noma de Madrid  Cantoblanco 28049 Madrid Spain"},{"name":"IMDEA-Nanociencia  c\/Faraday 9 Cantoblanco 28049 Madrid Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0002-7049","authenticated-orcid":false,"given":"M. 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