{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T02:36:13Z","timestamp":1767839773512,"version":"3.49.0"},"reference-count":42,"publisher":"Wiley","issue":"27","license":[{"start":{"date-parts":[[2025,4,2]],"date-time":"2025-04-02T00:00:00Z","timestamp":1743552000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["200020\u2013184607"],"award-info":[{"award-number":["200020\u2013184607"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["20020\u2013207359"],"award-info":[{"award-number":["20020\u2013207359"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007514","name":"Universit\u00e0 di Pisa","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007514","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006389","name":"Universit\u00e9 de Gen\u00e8ve","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100006389","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["200020"],"award-info":[{"award-number":["200020"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["207359"],"award-info":[{"award-number":["207359"]}],"id":[{"id":"10.13039\/501100001711","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,5,14]]},"abstract":"<jats:p>Boramidines are promising chromophores capable of circularly polarized luminescence (CPL). The synthesis, characterization, and photophysical analysis of novel BINOL\u2010 and H8\u2010BINOL\u2010tethered boramidines <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> are reported, leveraging the chiral perturbation strategy for CPL material design. These enantiopure compounds, prepared in a concise three\u2010step synthesis, exhibit high fluorescence quantum yields <jats:italic>\u03d5<\/jats:italic> (up to 95% in N\u2082\u2010saturated solutions) and luminescence dissymmetry factors (|<jats:italic>g<\/jats:italic><jats:sub>lum<\/jats:sub>| \u223c 10<jats:sup>\u2212<\/jats:sup><jats:sup>3<\/jats:sup>). Transient absorption spectroscopy and quantum\u2010chemical calculations provide insight into their singlet\u2010triplet spin\u2010orbit coupling and intersystem crossing mechanisms.<\/jats:p>","DOI":"10.1002\/chem.202500490","type":"journal-article","created":{"date-parts":[[2025,3,19]],"date-time":"2025-03-19T10:53:12Z","timestamp":1742381592000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Tethered Enantiopure Boramidines for Advanced Chiroptical Studies"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9025-4095","authenticated-orcid":false,"given":"Nidal","family":"Saleh","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry University of Geneva  Quai Ernest Ansermet 30 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7239-115X","authenticated-orcid":false,"given":"Valerio","family":"Zullo","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University of Geneva  Quai Ernest Ansermet 30 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Estefan\u00eda","family":"Sucre\u2010Rosales","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry University of Geneva  Quai Ernest Ansermet 30 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3563-894X","authenticated-orcid":false,"given":"Lorenzo","family":"Arrico","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica e Chimica Industriale University of Pisa  Via G. Moruzzi 13 Pisa 56124 Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6331-6219","authenticated-orcid":false,"given":"Francesco","family":"Zinna","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica e Chimica Industriale University of Pisa  Via G. Moruzzi 13 Pisa 56124 Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0869-5076","authenticated-orcid":false,"given":"Gennaro","family":"Pescitelli","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica e Chimica Industriale University of Pisa  Via G. Moruzzi 13 Pisa 56124 Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5699-9675","authenticated-orcid":false,"given":"C\u00e9line","family":"Besnard","sequence":"additional","affiliation":[{"name":"Laboratory of Crystallography University of Geneva  Quai Ernest Ansermet 24 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9580-9683","authenticated-orcid":false,"given":"Eric","family":"Vauthey","sequence":"additional","affiliation":[{"name":"Department of Physical Chemistry University of Geneva  Quai Ernest Ansermet 30 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6247-8059","authenticated-orcid":false,"given":"J\u00e9r\u00f4me","family":"Lacour","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University of Geneva  Quai Ernest Ansermet 30 Geneva 1211 Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,4,2]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201501178"},{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00770"},{"key":"e_1_2_8_1_3","doi-asserted-by":"publisher","DOI":"10.1007\/978-981-15-2309-0"},{"key":"e_1_2_8_1_4","author":"Li X.","year":"2021","journal-title":"Adv. Photonics Res."},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c05410"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002791"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC00870G"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000915)39:18<3252::AID-ANIE3252>3.0.CO;2-P"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b102376b"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja412294s"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochemrev.2022.100500"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b00850"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202010281"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr970463w"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1083622"},{"key":"e_1_2_8_9_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr040079g"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400568b"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407034"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02785"},{"key":"e_1_2_8_12_1","unstructured":"Performing the reaction with 2 3\u2010dichloropyridine instead of 1\u2010oxide 3 did not lead to the cyclized adducts 4 but to products of mono\u2010addition on each of the two oxygen groups of the BINOL moiety."},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202001063"},{"key":"e_1_2_8_14_1","unstructured":"Structural information was established by X\u2010ray diffraction analysis for (S)\u20105 (rac)\u20106 and (rac)\u20101 (Figures 2 S21\u2013S23 and Tables S3\u2013S5)."},{"key":"e_1_2_8_15_1","unstructured":"Deposition numbers 2416728 for (S)\u20105 2416729 for (rac)\u20106 and 2416730 for (rac)\u20101 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe viawww.ccdc.cam.ac.uk\/structures."},{"key":"e_1_2_8_16_1","unstructured":"Despite starting from enantiopure sources of BINOL and H8\u2010BINOL care was taken to verify and establish the enantiomeric purity of compounds (R)\u20106 (S)\u20106 (R)\u20109 and (S)\u20109 by chiral stationary phase HPLC. See Supporting information for details (Figures S19 and S20)."},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic50186a068"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00894-020-04374-9"},{"key":"e_1_2_8_19_1","unstructured":"a)For 2 crystallographic data could not be obtained but based on precedents it is likely that the angle between the biphenyl subunit is larger than in the case of 1. It will be later validated through DFT calculations;"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800022"},{"key":"e_1_2_8_20_1","unstructured":"Compounds 1 and 2 present solid\u2010state fluorescence properties (Figure S26) which were not studied further."},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23535"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.201800015"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp993864j"},{"key":"e_1_2_8_23_1","unstructured":"The data that support the findings of this study are openly available in yareta.unige.ch athttps:\/\/doi.org\/10.26037\/yareta:3qdyhsypmzhchkqc4rhdcppani. It will be preserved for 10 years."},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201602684"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.4812705"},{"key":"e_1_2_8_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_8_24_4","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.81"},{"key":"e_1_2_8_24_5","doi-asserted-by":"publisher","DOI":"10.1063\/1.472460"},{"key":"e_1_2_8_24_6","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314026370"},{"key":"e_1_2_8_24_7","volume-title":"SHELXL\u201097, Program for the Refinement of Crystal Structures","author":"Sheldrick G. M.","year":"1997"},{"key":"e_1_2_8_24_8","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_8_25_1","volume-title":"Gaussian 16, Revision A.03","author":"Frisch M. J.","year":"2016"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202500490","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T11:32:51Z","timestamp":1760700771000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202500490"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,2]]},"references-count":42,"journal-issue":{"issue":"27","published-print":{"date-parts":[[2025,5,14]]}},"alternative-id":["10.1002\/chem.202500490"],"URL":"https:\/\/doi.org\/10.1002\/chem.202500490","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,4,2]]},"assertion":[{"value":"2025-02-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-03-17","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500490"}}