{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T17:12:34Z","timestamp":1790183554603,"version":"4.1.0"},"reference-count":107,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T00:00:00Z","timestamp":1769558400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T00:00:00Z","timestamp":1769558400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100008084","name":"Neurof\u00f6rbundet","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008084","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["440719683"],"award-info":[{"award-number":["440719683"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2026,3,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    We present that halogen\u2010substituted and air\u2010stable Thiele\u2010type diradicaloids with folded (\n                    <jats:bold>1<\/jats:bold>\n                    ) and planar (\n                    <jats:bold>2<\/jats:bold>\n                    ,\n                    <jats:bold>3<\/jats:bold>\n                    ) structures can be obtained by switching the positions of fluorine and chlorine substituents. The strongly distorted\n                    <jats:italic>p<\/jats:italic>\n                    \u2010quinodimethane\n                    <jats:bold>1<\/jats:bold>\n                    demonstrates emission in the UV\u2013visible\/near\u2010infrared (UV\u2013vis\/NIR) range with a photoluminescence quantum yield (PLQY) of 100%, an exceedingly large Stokes shift of up to 2.0\u00a0eV, an excited state lifetime of 81\u00a0ns, and pronounced solvatochromic emission (from 1.81\u00a0eV in\n                    <jats:italic>n<\/jats:italic>\n                    \u2010pentane to approximately 2.0\u00a0eV in dichloromethane). Dual emission in pentane, transient absorption spectroscopy, quantum chemical calculations, as well as the comparison with compounds\n                    <jats:bold>2<\/jats:bold>\n                    and\n                    <jats:bold>3<\/jats:bold>\n                    reveal that the exceptional photophysical properties of closed\u2010shell\n                    <jats:bold>1<\/jats:bold>\n                    are thanks to interconversion with its planar conformer\n                    <jats:bold>\n                      1\n                      <jats:sup>flat<\/jats:sup>\n                    <\/jats:bold>\n                    . The key here is that the conformer\n                    <jats:bold>\n                      1\n                      <jats:sup>flat<\/jats:sup>\n                    <\/jats:bold>\n                    , which is generated upon photoexcitation, excels with a pronounced singlet diradical character (\n                    <jats:italic>y<\/jats:italic>\n                    <jats:sub>0<\/jats:sub>\n                    = 0.78) and a dark doubly excited (DE) S1 state. Our findings delineate how to leverage conformational equilibria to design bright luminescent materials based on hidden and thus air\u2010stable organic diradicals.\n                  <\/jats:p>","DOI":"10.1002\/anie.202524042","type":"journal-article","created":{"date-parts":[[2026,1,29]],"date-time":"2026-01-29T04:36:52Z","timestamp":1769661412000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Hidden Diradical: Conformational Switch for Solvatochromic NIR Emission With Unity Quantum Yield in Thiele's Hydrocarbon"],"prefix":"10.1002","volume":"65","author":[{"given":"Matteo","family":"Bevilacqua","sequence":"first","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"},{"name":"Coordination Chemistry Saarland University  Saarbr\u00fccken Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6487-3084","authenticated-orcid":false,"given":"Mattia","family":"Reato","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4121-1694","authenticated-orcid":false,"given":"Federico","family":"Cilento","sequence":"additional","affiliation":[{"name":"Elettra\u2010Sincrotrone Trieste S.C.p.A  Basovizza Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9908-6961","authenticated-orcid":false,"given":"Claudia","family":"Graiff","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche, della Vita e della Sostenibilit\u00e0 Ambientale Universit\u00e0 di Parma  Parma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0090-9922","authenticated-orcid":false,"given":"Sabrina","family":"Antonello","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8101-4022","authenticated-orcid":false,"given":"Luca","family":"Schio","sequence":"additional","affiliation":[{"name":"CNR \u2013 Istituto Officina dei Materiali (IOM) Basovizza, Trieste Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2647-9967","authenticated-orcid":false,"given":"Alessandro","family":"Aliprandi","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7724-735X","authenticated-orcid":false,"given":"Cristina","family":"Tubaro","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3548-4423","authenticated-orcid":false,"given":"Lorenzo","family":"Franco","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1228-2458","authenticated-orcid":false,"given":"Martina","family":"Dell'Angela","sequence":"additional","affiliation":[{"name":"CNR \u2013 Istituto Officina dei Materiali (IOM) Basovizza, Trieste Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3412-651X","authenticated-orcid":false,"given":"Dominik","family":"Munz","sequence":"additional","affiliation":[{"name":"Coordination Chemistry Saarland University  Saarbr\u00fccken Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6762-2240","authenticated-orcid":false,"given":"Marco","family":"Baron","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche Universit\u00e0 degli Studi di Padova  Padova Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,1,28]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00406"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00376"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00255"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.4114"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00260"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400056a"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.02.010"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201814544"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502303"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b12683"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC03667C"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2518"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206680"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201503650"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2EE01600A"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b10762"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS01433H"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.3c00613"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41563\u2010020\u20100705\u20109"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010018\u20100695\u20109"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c00306"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.3225202"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202300772"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.4c01379"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202500284"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c11585"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC03673A"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/agt2.70100"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c10608"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202513593"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202423470"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c11116"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010023\u201006222\u20101"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c04360"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c04340"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c05718"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.4c01632"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1098\/rspa.2023.0599"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570\u2010020\u20100200\u20105"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41377\u2010023\u201001314\u2010z"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja070946"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201903007"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.4c00895"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c03972"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c01076"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.4c13338"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c11549"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c13270"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.3c00482"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009\u20102614(75)80169\u20102"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c05251"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c05009"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19040370245"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00279a056"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404853"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202500749"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202001286"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202400879"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC05779H"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201904421"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201713346"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CC02092H"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310975"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja4104765"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1611887"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202406076"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202500943"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010021\u201027104\u2010y"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c00236"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5CC00053J"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02318"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b02432"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC04489J"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916089"},{"key":"e_1_2_8_76_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04096J"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b09646"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00018a046"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197505751"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00496a005"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar50135a002"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00718"},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b09611"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja961829"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00061a029"},{"key":"e_1_2_8_86_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC01999A"},{"key":"e_1_2_8_87_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202200286"},{"key":"e_1_2_8_88_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.1c00664"},{"key":"e_1_2_8_89_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja3050579"},{"key":"e_1_2_8_90_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200501118"},{"key":"e_1_2_8_91_1","unstructured":"The unit cell contains two independent molecules of1 yet the values for only one thereof are given here. For comparison with the other molecule see the SI."},{"key":"e_1_2_8_92_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5SC04257G"},{"key":"e_1_2_8_93_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja049809s"},{"key":"e_1_2_8_94_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201503927"},{"key":"e_1_2_8_95_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2023.101691"},{"key":"e_1_2_8_96_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202404376"},{"key":"e_1_2_8_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja404198h"},{"key":"e_1_2_8_98_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02318"},{"key":"e_1_2_8_99_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr940745l"},{"key":"e_1_2_8_100_1","doi-asserted-by":"publisher","DOI":"10.18637\/jss.v049.i03"},{"key":"e_1_2_8_101_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC00699H"},{"key":"e_1_2_8_102_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac60210a007"},{"key":"e_1_2_8_103_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.70019"},{"key":"e_1_2_8_104_1","doi-asserted-by":"publisher","DOI":"10.1063\/5.0072129"},{"key":"e_1_2_8_105_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5CP00881F"},{"key":"e_1_2_8_106_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206390"},{"key":"e_1_2_8_107_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr1002613"},{"key":"e_1_2_8_108_1","unstructured":"Various methods have been proposed in the literature to compute diradical indicesy0. Here the diradical charactery0refers to the occupation number of the lowest unoccupied natural orbital (natural orbital occupation number NOON) of the S0 ground state according to CASSCF(14 14). See the SI for other methods which afford values betweeny0= 0.63\u20130.96."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202524042","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202524042","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202524042","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T16:57:25Z","timestamp":1790182645000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202524042"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,1,28]]},"references-count":107,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2026,3,2]]}},"alternative-id":["10.1002\/anie.202524042"],"URL":"https:\/\/doi.org\/10.1002\/anie.202524042","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,1,28]]},"assertion":[{"value":"2025-10-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-01-19","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-01-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e24042"}}