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Nitrone exhibits remarkable versatility and applicability in bioorthogonal labeling due to its high reactivity with strained alkynes via the strain-promoted alkyne\u2013nitrone cycloaddition (SPANC) reaction. In this work, four cyclometalated iridium(III) polypyridine complexes functionalized with two nitrone units were designed as novel phosphorogenic bioorthogonal reagents for bioimaging and phototherapeutics. The complexes showed efficient emission quenching, which is attributed to an efficient nonradiative decay pathway via the low-lying T1\/S0 minimum energy crossing point (MECP), as revealed by computational studies. However, the complexes displayed significant emission enhancement and lifetime extension upon reaction with (1R,8S,9s)-bicyclo[6.1.0]non-4-yne (BCN) derivatives. In particular, they showed a remarkably higher reaction rate toward a bis-cyclooctyne derivative (bis-BCN) compared with its monomeric counterpart (mono-BCN). Live-cell imaging and (photo)cytotoxicity studies revealed higher photocytotoxicity in bis-BCN-pretreated cells, which is ascribed to the enhanced singlet oxygen (1O2) photosensitization resulting from the elimination of the nitrone-associated quenching pathway. Importantly, the cross-linking properties and enhanced reactivity of the complexes make them highly promising candidates for the development of hydrogels and stapled\/cyclized peptides, offering intriguing photophysical, photochemical, and biological properties. Notably, a nanosized hydrogel (2-gel) demonstrated potential as a drug delivery system, while a stapled peptide (2-bis-pDIKK) exhibited p53-Mdm2 inhibitory activity related to apoptosis and a cyclized peptide (2-bis-RGD) showed cancer selectivity.<\/jats:p>","DOI":"10.1021\/jacs.4c07251","type":"journal-article","created":{"date-parts":[[2024,9,9]],"date-time":"2024-09-09T10:25:55Z","timestamp":1725877555000},"page":"25589-25599","source":"Crossref","is-referenced-by-count":18,"title":["Exploiting\nthe Potential of Iridium(III)\n                    <i>bis<\/i>\n                    -Nitrone Complexes\nas Phosphorogenic Bifunctional Reagents for Phototheranostics"],"prefix":"10.1021","volume":"146","author":[{"given":"Eunice Chiu-Lam","family":"Mak","sequence":"first","affiliation":[{"name":"City University of Hong Kong , , Tat Chee Avenue , , ,","place":["Kowloon, Hong Kong, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7407-0840","authenticated-orcid":true,"given":"Ziyong","family":"Chen","sequence":"additional","affiliation":[{"name":"The University of Hong Kong , , Pokfulam Road , ,","place":["Hong Kong, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lawrence Cho-Cheung","family":"Lee","sequence":"additional","affiliation":[{"name":"City University of Hong Kong , , Tat Chee Avenue , , ,","place":["Kowloon, Hong Kong, P. R. China"]},{"name":"Laboratory for Synthetic Chemistry and Chemical Biology Limited , Units 1503-1511, 15\/F, Building 17 W, Hong Kong Science Park , , ,","place":["New Territories, Hong Kong, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6050-5276","authenticated-orcid":true,"given":"Peter Kam-Keung","family":"Leung","sequence":"additional","affiliation":[{"name":"City University of Hong Kong , , Tat Chee Avenue , , ,","place":["Kowloon, Hong Kong, P. R. China"]},{"name":"City University of Hong Kong , , Tat Chee Avenue , , ,","place":["Kowloon, Hong Kong, P. R. China"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2436-3047","authenticated-orcid":true,"given":"Alex Man-Hei","family":"Yip","sequence":"additional","affiliation":[{"name":"City University of Hong Kong , , Tat Chee Avenue , , ,","place":["Kowloon, Hong Kong, P. R. China"]},{"name":"Laboratory for Synthetic Chemistry and Chemical Biology Limited , Units 1503-1511, 15\/F, Building 17 W, Hong Kong Science Park , , ,","place":["New Territories, Hong Kong, P. R. 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