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In this context, the proper selection of precursors and synthetic conditions is of paramount importance when tailoring the photocatalytic features of the resulting nanomaterials. Herein, a novel <jats:italic>bottom\u2010up<\/jats:italic> methodology has been developed for the preparation of phenol\u2010rich CDs (<jats:italic>Ph<\/jats:italic>\u2010CDs) that allowed us to capitalize on the excellent photoredox properties of surface phenolate anions that can be obtained upon deprotonation of <jats:italic>Ph<\/jats:italic>\u2010CDs. Specifically, in this study, <jats:italic>Ph<\/jats:italic>\u2010CDs are used in combination with a suitable base and an organocatalyst, namely the Schreiner thiourea (<jats:bold>A<\/jats:bold>), to drive valuable [3\u2009+\u20092] photocycloaddition reactions between suitable cyclopropyl ketones <jats:bold>1<\/jats:bold> and unsaturated hydrocarbons <jats:bold>2<\/jats:bold>. Mechanistic studies show the key role played by <jats:bold>A<\/jats:bold> in the transformation. In fact, this organocatalyst may not only activate the carbonyl moiety of <jats:bold>1<\/jats:bold> but also stabilize the formation and enhance the photocatalytic performances of phenolate anions on the nanoparticle surfaces. Remarkably, this photocatalytic transformation provides a wide variety of densely functionalized five\u2010membered rings <jats:bold>3<\/jats:bold> (<jats:italic>17 examples, up to 99% yield<\/jats:italic>) under mild operative conditions. Lastly, it is demonstrated that <jats:italic>Ph<\/jats:italic>\u2010CDs can be easily recovered and reused up to three times without any significant drop in yield.<\/jats:p>","DOI":"10.1002\/cssc.202500521","type":"journal-article","created":{"date-parts":[[2025,4,3]],"date-time":"2025-04-03T14:48:29Z","timestamp":1743691709000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Phenol\u2010Rich Carbon Dots as Metal\u2010Free Nano\u2010Photocatalysts for [3\u2009+\u20092] Cycloaddition Reactions"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5981-1295","authenticated-orcid":false,"given":"Martina","family":"Mamone","sequence":"first","affiliation":[{"name":"Department of Chemical and Pharmaceutical Sciences INSTM UdR Trieste University of Trieste  Via Licio Giorgieri 1 34127 Trieste 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