{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T02:11:14Z","timestamp":1792807874587,"version":"4.5.0"},"reference-count":146,"publisher":"Wiley","issue":"29","license":[{"start":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T00:00:00Z","timestamp":1747267200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["advanced.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Advanced Materials"],"published-print":{"date-parts":[[2025,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A way to prevent the fast configurational interconversion of tertiary amines is to invoke Tr\u00f6ger's base analogs, which display methano\u2010 or ethano\u2010bridged diazocine cores fused to aromatic rings. These derivatives are configurationally stable, even in acidic media when their structures bear ethylene bridges. Here, a two\u2010 to three\u2010step synthesis is presented of methano\u2010 and ethano\u2010bridged Tr\u00f6ger's base analogs with two peripheral fluorophores, i.e., anthracene, pyrene, and 9,9\u2010dimethylfluorene units. These compounds, possessing two nitrogen stereogenic centers, exhibit good circularly polarized luminescence (CPL) dissymmetry factors (|<jats:italic>g<\/jats:italic><jats:sub>lum<\/jats:sub>| up to 1.2 \u00d7 10<jats:sup>\u22123<\/jats:sup>) and brightnesses (<jats:italic>B<\/jats:italic><jats:sub>CPL<\/jats:sub> up to 26.3 M<jats:sup>\u22121<\/jats:sup> cm<jats:sup>\u22121<\/jats:sup>), as well as excellent fluorescence quantum yields, demonstrating the Tr\u00f6ger\u00b4s base core to be a convenient scaffold to prepare CPL emitters upon functionalization with simple achiral fluorophores. Furthermore, the configurationally stable ethano\u2010bridged Tr\u00f6ger's base analogs are employed to modulate their CPL response, generating a CPL switch through their protonation\/deprotonation by consecutive additions of acid and base. The reversibility of the switching process is demonstrated for two cycles without altering the CPL performance of the molecule. It is believed that this straightforward and efficient approach to building CPL emitters employing the Tr\u00f6ger's base core could lead to its incorporation in CPL\u2010based sensors and materials.<\/jats:p>","DOI":"10.1002\/adma.202417326","type":"journal-article","created":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T04:41:39Z","timestamp":1747284099000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Acid\/Base\u2010Responsive Circularly Polarized Luminescence Emitters with Configurationally Stable Nitrogen Stereogenic Centers"],"prefix":"10.1002","volume":"37","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5270-1675","authenticated-orcid":false,"given":"Pablo","family":"Garc\u00eda\u2010Cerezo","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Facultad de Ciencias Unidad de Excelencia de Qu\u00edmica Aplicada a Biomedicina y Medioambiente (UEQ) Universidad de Granada (UGR)  Avda. 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G.","family":"David","sequence":"additional","affiliation":[{"name":"Department of Chemistry Northwestern University  2145 Sheridan Road Evanston IL 60208 USA"},{"name":"Laboratoire MOLTECH\u2010Anjou (UMR CNRS 6200) Universit\u00e9 Angers  2 Bd Lavoisier Angers Cedex 49045 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5239-0042","authenticated-orcid":false,"given":"Laura","family":"Le Bras","sequence":"additional","affiliation":[{"name":"CNRS Chrono\u2010environnement (UMR 6249) Universit\u00e9 Marie et Louis Pasteur  Besan\u00e7on F\u201025000 France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2472-5888","authenticated-orcid":false,"given":"Seifallah","family":"Abid","sequence":"additional","affiliation":[{"name":"Department of Chemistry Northwestern University  2145 Sheridan Road Evanston IL 60208 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2794-8390","authenticated-orcid":false,"given":"Xuesong","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Northwestern University  2145 Sheridan Road Evanston IL 60208 USA"},{"name":"Department of Chemistry University of Wyoming  Laramie WY 82072 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7876-3986","authenticated-orcid":false,"given":"Delia","family":"Miguel","sequence":"additional","affiliation":[{"name":"Nanoscopy\u2010UGR Laboratory. 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has been frequently employed for the resolution of Tr\u00f6ger\u2019s Base derivatives see the following selected examples:"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20318"},{"key":"e_1_2_7_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201200029"},{"key":"e_1_2_7_36_4","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2014.01.058"},{"key":"e_1_2_7_37_1","unstructured":"For the racemic resolution of5by co\u2010crystallization see:"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo401873x"},{"key":"e_1_2_7_37_3","first-page":"138","volume":"2","author":"Kazem\u2010Rostami M.","year":"2020","journal-title":"J. Med. Nanomater. Chem."},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ct400947t"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp506779y"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.27001"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA06832B"},{"key":"e_1_2_7_40_1","unstructured":"Note that the glum values are calculated asglum= 2(IL\u2212IR)\/(IL+IR) where ILand IRcorrespond to the intensities of left\u2010 and right\u2010handed circularly polarized light."},{"key":"e_1_2_7_41_1","unstructured":"BCPLis defined asBCPL= \u025b\u03bb\u00d7 \u03a6F\u00d7 |glum|\/2 being \u025b\u03bb the molar extinction coefficient at the excitation wavelength \u03bb; \u03a6F the fluorescence quantum yield; and |glum| the emission dissymmetry factor. See ref. 42."},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002791"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202316696"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202409998"},{"key":"e_1_2_7_44_1","unstructured":"For selected examples of CPL switching with discrete molecules see:"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja203206g"},{"key":"e_1_2_7_44_3","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC01277A"},{"key":"e_1_2_7_44_4","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC01748G"},{"key":"e_1_2_7_44_5","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC08395A"},{"key":"e_1_2_7_44_6","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b01860"},{"key":"e_1_2_7_44_7","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC01138B"},{"key":"e_1_2_7_44_8","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b07143"},{"key":"e_1_2_7_44_9","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201903252"},{"key":"e_1_2_7_44_10","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b13184"},{"key":"e_1_2_7_44_11","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC01959K"},{"key":"e_1_2_7_44_12","doi-asserted-by":"publisher","DOI":"10.1002\/adom.202300779"},{"key":"e_1_2_7_44_13","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319502"},{"key":"e_1_2_7_45_1","unstructured":"Although protonation results in many cases in a red\u2010shift of the photoluminescence band respect to that of the non\u2010protonated species on account of an increased electron\u2010withdrawing character there are reported examples of fluorophores functionalized with aniline groups that undergo hypsochromic shifts upon protonation. See for example:"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jz501383d"},{"key":"e_1_2_7_45_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2023.121758"},{"key":"e_1_2_7_46_1","unstructured":"Note that photodegradation was observed for compound3bin acidic medium after exhaustive irradiation during the CPL measurements."},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adj5328"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c08706"}],"container-title":["Advanced Materials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adma.202417326","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T17:03:05Z","timestamp":1759770185000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adma.202417326"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,5,15]]},"references-count":146,"journal-issue":{"issue":"29","published-print":{"date-parts":[[2025,7]]}},"alternative-id":["10.1002\/adma.202417326"],"URL":"https:\/\/doi.org\/10.1002\/adma.202417326","archive":["Portico"],"relation":{},"ISSN":["0935-9648","1521-4095"],"issn-type":[{"value":"0935-9648","type":"print"},{"value":"1521-4095","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,5,15]]},"assertion":[{"value":"2024-11-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2417326"}}