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Time\u2010dependent density functional theory (TD\u2010DFT) calculations were used to predict absorption maxima and to elucidate key structure\u2010property relationships, highlighting the dominant influence of substitution at position 4 of the aromatic ring of\n                    <jats:bold>1<\/jats:bold>\n                    . Guided by these results, a broad library of\n                    <jats:italic>o<\/jats:italic>\n                    \u2010amino\u2010TZDs\n                    <jats:bold>1<\/jats:bold>\n                    was designed and synthesized, including heteroaryl analogues. Photochemical investigations demonstrated that the sequence is highly robust, overall, proceeding efficiently across a wide range of substrates and displaying a broad tolerance toward variations in their electronic properties or substitution patterns. A detailed kinetic analysis using ex situ and in situ\n                    <jats:sup>1<\/jats:sup>\n                    H NMR experiments was conducted and enabled a quantitative comparison of reaction efficiencies as a function of substituents on the aromatic ring, the TZD core, and the exocyclic double bond, across series\n                    <jats:bold>1(a)<\/jats:bold>\n                    to\n                    <jats:bold>1(d)<\/jats:bold>\n                    . Overall, this work establishes a fine structure\u2010reactivity framework for this photochemical cascade, identifying the key parameters governing its efficiency.\n                  <\/jats:p>","DOI":"10.1002\/chem.71696","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T04:00:42Z","timestamp":1790740842000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["From Photoswitch to Polycycle: Structure\u2013Reactivity Relationships in the Photoinduced Isomerization\u2013Cyclization of Amino(hetero)arylidene\u2010thiazolidine\u20102,4\u2010diones"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0009-0000-5658-7291","authenticated-orcid":false,"given":"Vincent","family":"Bruneau","sequence":"first","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-5040-6030","authenticated-orcid":false,"given":"Johanne","family":"Coutard","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-7543-0787","authenticated-orcid":false,"given":"Nina","family":"Bukhtiiarova","sequence":"additional","affiliation":[{"name":"CNRS, CRM2 Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3078-7946","authenticated-orcid":false,"given":"Elodie","family":"Cortelazzo\u2010Polisini","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tran Hoang Thi","family":"Nguyen","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-1007-8059","authenticated-orcid":false,"given":"Sandrine","family":"Adach","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Axel Hans","family":"Gansm\u00fcller","sequence":"additional","affiliation":[{"name":"CNRS, CRM2 Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9475-5049","authenticated-orcid":false,"given":"Emmanuelle","family":"Bignon","sequence":"additional","affiliation":[{"name":"CNRS, LPCT Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6588-0027","authenticated-orcid":false,"given":"Michel","family":"Boisbrun","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3738-2359","authenticated-orcid":false,"given":"Corinne","family":"Comoy","sequence":"additional","affiliation":[{"name":"CNRS, L2CM Universit\u00e9 De Lorraine  Nancy France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,29]]},"reference":[{"key":"e_1_2_9_2_1","first-page":"792","volume-title":"Molecular Switches","author":"Wegner H. 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