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The fluorophore exhibits crystallization\u2010induced emission enhancement and pH\u2010dependent luminescence, attributable to a conformational lock in the crystalline state and suppression of nonemissive forms upon deprotonation. Extensive photophysical analysis reveals a quantum yield increase from 1% in solution to 22% in the solid state, along with a consistent emission wavelength irrespective of the state. Theoretical calculations show that the Excited\u2010State Intramolecular Proton Transfer (ESIPT) mechanism is facilitated by the unique orientation of acetyl substituents and a strong intramolecular hydrogen bond in the solid state and rationalized the large Stokes\u2019 shift observed. We explore the role of crystallization and intramolecular interactions in modifying the photophysical behavior of the fluorophore, emphasizing the absence of solvatochromism and the distinctive absence of strong intermolecular interactions in the solid state. Further theoretical modeling underscores the interplay between geometric conformation and proton transfer in determining emission properties, which is dramatically altered upon deprotonation. Therefore, detailed theoretical approaches to comprehensively map the complete photophysical landscape offer critical insights for the design and synthesis of small molecules that outperform larger fluorophores while retaining stimuli\u2010responsive properties.<\/jats:p>","DOI":"10.1002\/chem.202501178","type":"journal-article","created":{"date-parts":[[2025,5,21]],"date-time":"2025-05-21T08:55:21Z","timestamp":1747817721000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Single\u2010Benzene Fluorophore with Enhanced Emission: Insights into Photophysical Properties through Proton Transfer Mapping"],"prefix":"10.1002","volume":"31","author":[{"given":"Lu\u00eds F. B.","family":"Fontes","sequence":"first","affiliation":[{"name":"LAQV\u2010REQUIMTE Department of Chemistry University of Aveiro  Campus de Santiago Aveiro 3810\u2010193 Portugal"},{"name":"CICECO\u2010Aveiro Institute of Materials Department of Chemistry University of Aveiro  Campus de Santiago Aveiro 3810\u2010193 Portugal"}]},{"given":"Jo\u00e3o","family":"Rocha","sequence":"additional","affiliation":[{"name":"CICECO\u2010Aveiro Institute of Materials Department of Chemistry University of Aveiro  Campus de Santiago Aveiro 3810\u2010193 Portugal"}]},{"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV\u2010REQUIMTE Department of Chemistry University of Aveiro  Campus de Santiago Aveiro 3810\u2010193 Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7439-209X","authenticated-orcid":false,"given":"Samuel","family":"Guieu","sequence":"additional","affiliation":[{"name":"LAQV\u2010REQUIMTE Department of Chemistry University of Aveiro  Campus de Santiago Aveiro 3810\u2010193 Portugal"}]}],"member":"311","published-online":{"date-parts":[[2025,6]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.3c02244"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00464J"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00263"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.5c00774"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.07.107"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB02387F"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502365"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0TC00776E"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-25677-2"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1908516116"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC05557C"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301540"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100391a034"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11164-015-2343-4"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(94)00957-0"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2005.07.002"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/dt9830002429"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600536807062162"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15113d"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002307"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1070\/RC2011v080n06ABEH004144"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp300340t"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo502080p"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/P298700000S1"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.1c00831"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cp23879a"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26175140"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b08562"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202201844"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202501178","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:14:04Z","timestamp":1760278444000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202501178"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6]]},"references-count":29,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2025,8]]}},"alternative-id":["10.1002\/chem.202501178"],"URL":"https:\/\/doi.org\/10.1002\/chem.202501178","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2025,6]]},"assertion":[{"value":"2025-03-25","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-21","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-06-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202501178"}}