{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T15:58:19Z","timestamp":1787241499718,"version":"build-2736575974"},"reference-count":88,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2022,12,20]],"date-time":"2022-12-20T00:00:00Z","timestamp":1671494400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2023,1,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Helicenes combine two central themes in chemistry: extended \u03c0\u2010conjugation and chirality. Hetero\u2010atom doping preserves both characteristics and allows modulation of the electronic structure of a helicene. Herein, we report the (BO)\n                    <jats:sub>2<\/jats:sub>\n                    \u2010doped tetrathia[7]helicene\n                    <jats:bold>1<\/jats:bold>\n                    , which was prepared from 2\u2010methoxy\u20103,3\u2032\u2010bithiophene in four steps.\n                    <jats:bold>1<\/jats:bold>\n                    is formally derived by substituting two (Mes)B\u2212O moieties in place of (H)C=C(H) fragments in two benzene rings of the parent tetrathia[7]helicene. X\u2010ray crystallography revealed a dihedral angle of 50.26(9)\u00b0 between the two terminal thiophene rings. The (\n                    <jats:italic>P<\/jats:italic>\n                    )\u2010\/(\n                    <jats:italic>M<\/jats:italic>\n                    )\u2010\n                    <jats:bold>1<\/jats:bold>\n                    enantiomers were separated by chiral HPLC and are configurationally stable at room temperature. The experimentally determined enantiomerization barrier of 27.4\u00b10.1\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    is lower than that of tetrathia[7]helicene (39.4\u00b10.1\u2005kcal\u2009mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    ). The circular dichroism spectra of (\n                    <jats:italic>P<\/jats:italic>\n                    )\u2010 and (\n                    <jats:italic>M<\/jats:italic>\n                    )\u2010\n                    <jats:bold>1<\/jats:bold>\n                    show a perfect mirror\u2010image relationship.\n                    <jats:bold>1<\/jats:bold>\n                    is a blue emitter (\n                    <jats:italic>\u03bb<\/jats:italic>\n                    <jats:sub>em<\/jats:sub>\n                    =411\u2005nm) with a photoluminescence quantum efficiency of\n                    <jats:italic>\u03a6<\/jats:italic>\n                    <jats:sub>PL<\/jats:sub>\n                    =6\u2009% (\n                    <jats:italic>cf<\/jats:italic>\n                    . tetrathia[7]helicene:\n                    <jats:italic>\u03bb<\/jats:italic>\n                    <jats:sub>em<\/jats:sub>\n                    \u2248405\u2005nm,\n                    <jats:italic>\u03a6<\/jats:italic>\n                    <jats:sub>PL<\/jats:sub>\n                    =5\u2009%).\n                  <\/jats:p>","DOI":"10.1002\/anie.202215468","type":"journal-article","created":{"date-parts":[[2022,11,21]],"date-time":"2022-11-21T11:40:22Z","timestamp":1669030822000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["(BO)\n                    <sub>2<\/sub>\n                    \u2010Doped Tetrathia[7]helicene: A Configurationally Stable Blue Emitter"],"prefix":"10.1002","volume":"62","author":[{"given":"Luigi","family":"Menduti","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Anorganische Chemie Goethe-Universit\u00e4t Frankfurt Max-von-Laue-Strasse 7 60438 Frankfurt (Main) Germany"},{"name":"Dipartimento di Chimica Universit\u00e0 degli Studi di Milano Via Camillo Golgi 19 20133 Milano Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Clara","family":"Baldoli","sequence":"additional","affiliation":[{"name":"CNR Istituto di Scienze e Tecnologie Chimiche Giulio Natta Via Camillo Golgi 19 20133 Milano Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simone","family":"Manetto","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica e Tecnologie del Farmaco Sapienza Universit\u00e0 di Roma P.le A. Moro 5 00185 Roma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Bolte","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische Chemie Goethe-Universit\u00e4t Frankfurt Max-von-Laue-Strasse 7 60438 Frankfurt (Main) Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hans\u2010Wolfram","family":"Lerner","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische Chemie Goethe-Universit\u00e4t Frankfurt Max-von-Laue-Strasse 7 60438 Frankfurt (Main) Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giovanna","family":"Longhi","sequence":"additional","affiliation":[{"name":"Dipartimento di Medicina Molecolare e Traslazionale Universit\u00e0 di Brescia Viale Europa 11 25123 Brescia Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudio","family":"Villani","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica e Tecnologie del Farmaco Sapienza Universit\u00e0 di Roma P.le A. Moro 5 00185 Roma Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0168-9295","authenticated-orcid":false,"given":"Emanuela","family":"Licandro","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica Universit\u00e0 degli Studi di Milano Via Camillo Golgi 19 20133 Milano Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthias","family":"Wagner","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Anorganische Chemie Goethe-Universit\u00e4t Frankfurt Max-von-Laue-Strasse 7 60438 Frankfurt (Main) Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,12,20]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200087r"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35134J"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-017-0045"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00033"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202004488"},{"key":"e_1_2_7_7_1","unstructured":"\u00a0"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00449"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00076"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00183H"},{"key":"e_1_2_7_11_1","unstructured":"\u00a0"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC07208E"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03167"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC03115D"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja310372f"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3tc00040k"},{"key":"e_1_2_7_18_1","unstructured":"For 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Chem."},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02619"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201900044"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202100356"},{"key":"e_1_2_7_64_1","unstructured":"Deposition numbers\u20052211410 (for1) CCDC 2211405 (for2) CCDC 2211406 (for3) CCDC 2211409 (fortrans-4) CCDC 2211407 (for5) CCDC 2211408 (for6) and CCDC 2211411 (for4H2)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt51035b"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2016.01.054"},{"key":"e_1_2_7_67_1","unstructured":"Full details are provided in the Supporting Information."},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00741a025"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm010093z"},{"key":"e_1_2_7_70_1","unstructured":"\u00a0"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo034344u"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2017.09.006"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.59.2429"},{"key":"e_1_2_7_74_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja950774t"},{"key":"e_1_2_7_75_1","unstructured":"\u00a0"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp304576g"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp4105695"},{"key":"e_1_2_7_78_1","unstructured":"\u00a0"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.3390\/catal12040366"},{"key":"e_1_2_7_80_2","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1002\/9783527829415.ch11","volume-title":"Helicenes Synth. Prop. Appl.","author":"Abbate S.","year":"2022"},{"key":"e_1_2_7_81_1","unstructured":"\u00a0"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC08191J"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_2_7_84_1","unstructured":"Enantiomerization is the reversible conversion of a single enantiomer into the other one. The corresponding rate constant iskenant. Racemization is the irreversible conversion of a sample of single enantiomers or of a non-racemic mixture of enantiomers into the racemate. The corresponding rate constant iskrac. Comparison of calculated and experimental energy barriers was done using the enantiomerization barrier obtained fromkenant which is calculated from the experimentally determinedkracaccording to:kenant=0.5krac=8.15\u00d710\u22125\u2009s\u22121. The free energy for the enantiomerization process (\u0394Genant\u2260) was obtained by using the Eyring equation and setting a transmission coefficient equal to 1."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202215468","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202215468","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202215468","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T08:54:20Z","timestamp":1701420860000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202215468"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,12,20]]},"references-count":88,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2023,1,26]]}},"alternative-id":["10.1002\/anie.202215468"],"URL":"https:\/\/doi.org\/10.1002\/anie.202215468","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,12,20]]},"assertion":[{"value":"2022-10-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-12-20","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202215468"}}