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By employing a combination of X\u2010ray and electron crystallography, absorption and emission spectroscopy, time resolved fluorescence and ultrafast pump\u2010probe spectroscopy (visible and infrared) we unravel the correlation between the structure and light\u2010matter response, with a particular emphasis on the influence of the polarity of the surrounding environment. Our experimental results and simulations confirm that in polar and good hydrogen\u2010bond acceptor solvents (DMSO), the formation of dimers for ODIN derivatives is strongly inhibited. The presence of a phenyl group linked to the ureidic unit favors the folding of ODIN derivatives (forming an intramolecular hydrogen bond) leading to the stabilization of a charge\u2010transfer excited state which almost completely quenches its fluorescence emission. In solvents with a poor aptitude for forming hydrogen bonds, the formation of dimers is favored and gives rise to H aggregates, with a consequent considerable reduction in the fluorescence emission. The urea\u2010bound phenyl group furtherly stabilizes the dimers in chloroform.<\/jats:p>","DOI":"10.1002\/chem.202302619","type":"journal-article","created":{"date-parts":[[2023,10,3]],"date-time":"2023-10-03T22:48:23Z","timestamp":1696373303000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Tuning the Optical Properties Through Hydrogen Bond\u2010assisted H\u2010aggregate Formation: The ODIN Case"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6290-9119","authenticated-orcid":false,"given":"Francesco","family":"Bertocchi","sequence":"first","affiliation":[{"name":"Department of Chemistry Life Sciences and Environmental Sustainability University of Parma, and INSTM, UdR Parma  Parco Area delle Scienze17\/A 43124 Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4602-9373","authenticated-orcid":false,"given":"Danilo","family":"Marchetti","sequence":"additional","affiliation":[{"name":"Department of Chemistry Life Sciences and Environmental Sustainability University of Parma, and INSTM, UdR Parma  Parco Area delle Scienze17\/A 43124 Parma Italy"},{"name":"Istituto Italiano di Tecnologia Center for Materials Interfaces, Electron Crystallography  Viale Rinaldo Piaggio 34 56025 Pontedera Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9440-1643","authenticated-orcid":false,"given":"Sandra","family":"Doria","sequence":"additional","affiliation":[{"name":"ICCOM-CNR  via Madonna del Piano 10 I-50019 Sesto Fiorentino FI Italy"},{"name":"LENS (European Laboratory for Non-Linear Spectroscopy)  Via N. 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