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The key structural feature that converts the non\u2010fluorescent cycloalkyne\/triazole pair to its fluorescent counterpart is the pi\u2010acceptor group (COOMe, CN) at the C6 position of the isocoumarin ring. The design of the fluorescent cycloalkyne\/triazole pairs is based on the theoretical study of the S1 state deactivation mechanism of the non\u2010fluorescent isocoumarin\u2010fused cycloalkyne <jats:bold>IC9O<\/jats:bold> using multi\u2010configurational ab initio and DFT methodologies. The calculations revealed that deactivation proceeds through the electrocyclic ring opening of the \u03b1\u2010pyrone cycle and is accompanied by a redistribution of electron density in the fused benzene ring. We proposed that the S1 excited state deactivation barrier could be increased by introducing a pi\u2010acceptor group into a position that is in direct conjugation with the formed C=O group and has a reduced electron density in the transition state. As a proof of concept, we designed and synthesized two fluorescent isocoumarin\u2010fused cycloalkynes <jats:bold>IC9O<\/jats:bold>\u2010<jats:bold>COOMe<\/jats:bold> and <jats:bold>IC9O<\/jats:bold>\u2010<jats:bold>CN<\/jats:bold> bearing pi\u2010acceptors at the C6 position. The importance of the nature of a pi\u2010acceptor group was shown by the example of much less fluorescent CF<jats:sub>3<\/jats:sub>\u2010substituted cycloalkyne <jats:bold>IC9O<\/jats:bold>\u2010<jats:bold>CF<jats:sub>3<\/jats:sub><\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.202300540","type":"journal-article","created":{"date-parts":[[2023,6,9]],"date-time":"2023-06-09T06:57:10Z","timestamp":1686293830000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Development of Fluorescent Isocoumarin\u2010Fused Oxacyclononyne \u2013 1,2,3\u2010Triazole Pairs"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3571-2628","authenticated-orcid":false,"given":"Aleksandra A.","family":"Vidyakina","sequence":"first","affiliation":[{"name":"Institute of Chemistry Saint Petersburg State University (SPbU)  Sankt-Peterburg 199034 Saint Petersburg 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