{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T15:52:58Z","timestamp":1791906778516,"version":"4.3.4"},"reference-count":56,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,12,16]],"date-time":"2023-12-16T00:00:00Z","timestamp":1702684800000},"content-version":"am","delay-in-days":341,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2023,1,9]],"date-time":"2023-01-09T00:00:00Z","timestamp":1673222400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE- FG02-03ER15411"],"award-info":[{"award-number":["DE- FG02-03ER15411"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE-FG02-04ER15570"],"award-info":[{"award-number":["DE-FG02-04ER15570"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE-AC02-05CH11231"],"award-info":[{"award-number":["DE-AC02-05CH11231"]}],"id":[{"id":"10.13039\/100000015","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education of the Russian Federation","doi-asserted-by":"publisher","award":["075-15-2021-597"],"award-info":[{"award-number":["075-15-2021-597"]}],"id":[{"id":"10.13039\/501100012190","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":[[2023,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The simplest polycyclic aromatic hydrocarbon (PAH) carrying a five\u2010membered ring\u20149<jats:italic>H<\/jats:italic>\u2010fluorene (C<jats:sub>13<\/jats:sub>H<jats:sub>10<\/jats:sub>)\u2014is produced isomer\u2010specifically in the gas phase by reacting benzyl (C<jats:sub>7<\/jats:sub>H<jats:sub>7<\/jats:sub>\u22c5) with phenyl (C<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>\u22c5) radicals in a pyrolytic reactor coupled with single photon ionization mass spectrometry. The unconventional mechanism of reaction is supported by theoretical calculations, which first produces diphenylmethane and unexpected 1\u2010(6\u2010methylenecyclohexa\u20102,4\u2010dienyl)benzene intermediates (C<jats:sub>13<\/jats:sub>H<jats:sub>12<\/jats:sub>) accessed via addition of the phenyl radical to the <jats:italic>ortho<\/jats:italic> position of the benzyl radical. These findings offer convincing evidence for molecular mass growth processes defying conventional wisdom that radical\u2010radical reactions are initiated through recombination at their radical centers. The structure of 9<jats:italic>H<\/jats:italic>\u2010fluorene acts as a molecular building block for complex curved nanostructures like fullerenes and nanobowls providing fundamental insights into the hydrocarbon evolution in high temperature settings.<\/jats:p>","DOI":"10.1002\/anie.202216972","type":"journal-article","created":{"date-parts":[[2022,12,16]],"date-time":"2022-12-16T12:00:29Z","timestamp":1671192029000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Unconventional Pathway in the Gas\u2010Phase Synthesis of 9<i>H<\/i>\u2010Fluorene (C<sub>13<\/sub>H<sub>10<\/sub>) via the Radical\u2013Radical Reaction of Benzyl (C<sub>7<\/sub>H<sub>7<\/sub>) with Phenyl (C<sub>6<\/sub>H<sub>5<\/sub>)"],"prefix":"10.1002","volume":"62","author":[{"given":"Chao","family":"He","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Hawai'i at M\u0101noa  Honolulu HI-96822 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7233-7206","authenticated-orcid":false,"given":"Ralf I.","family":"Kaiser","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Hawai'i at M\u0101noa  Honolulu HI-96822 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenchao","family":"Lu","sequence":"additional","affiliation":[{"name":"Chemical Sciences Division Lawrence Berkeley National Laboratory  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Musahid","family":"Ahmed","sequence":"additional","affiliation":[{"name":"Chemical Sciences Division Lawrence Berkeley National Laboratory  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pavel S.","family":"Pivovarov","sequence":"additional","affiliation":[{"name":"Samara National Research University  Samara 443086 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oleg V.","family":"Kuznetsov","sequence":"additional","affiliation":[{"name":"Samara National Research University  Samara 443086 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marsel V.","family":"Zagidullin","sequence":"additional","affiliation":[{"name":"Samara National Research University  Samara 443086 Russian Federation"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander M.","family":"Mebel","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry Florida International University  Miami FL-33199 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,1,9]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","first-page":"222","volume":"12","author":"Berthelot M.","year":"1867","journal-title":"Ann. Chim. Farm. Ann. Chim. Fiz"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr60075a002"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/173635a0"},{"key":"e_1_2_3_5_1","unstructured":"M. Danzik PhD. Dissertation Thesis University of Cincinnati 1963."},{"key":"e_1_2_3_6_1","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","unstructured":"D.\u2005K. Greene PhD Dissertation Thesis Wright State University 2017;"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/mz400126f"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol025972l"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900182s"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000013v"},{"key":"e_1_2_3_12_1","unstructured":"\u00a0"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO;2-N"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0079-6700(00)00034-4"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3927(20011101)22:17<1365::AID-MARC1365>3.0.CO;2-B"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.1266"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-4095(20020404)14:7<477::AID-ADMA477>3.0.CO;2-9"},{"key":"e_1_2_3_18_1","unstructured":"\u00a0"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1576906"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200305504"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1369-7021(04)00399-2"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050152i"},{"key":"e_1_2_3_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm900788e"},{"key":"e_1_2_3_24_1","unstructured":"\u00a0"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-4095(200004)12:7<498::AID-ADMA498>3.0.CO;2-H"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900073s"},{"key":"e_1_2_3_27_1","unstructured":"\u00a0"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1086\/167501"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404537"},{"key":"e_1_2_3_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201404537"},{"key":"e_1_2_3_30_1","unstructured":"\u00a0"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA02744B"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0010-2180(99)00032-2"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1945-5100.1997.tb01292.x"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.pss.2018.09.003"},{"key":"e_1_2_3_35_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10573-005-0083-2"},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.proci.2004.08.281"},{"key":"e_1_2_3_37_1","unstructured":"\u00a0"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.combustflame.2021.02.010"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.1c02062"},{"key":"e_1_2_3_40_1","unstructured":"\u00a0"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jaerosci.2012.12.008"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.combustflame.2019.05.013"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.9b07017"},{"key":"e_1_2_3_44_1","unstructured":"\u00a0"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.1c03733"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpclett.8b01020"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP02930C"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jz200715u"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CP03846F"},{"key":"e_1_2_3_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202110929"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202110929"},{"key":"e_1_2_3_51_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1743867"},{"key":"e_1_2_3_52_1","doi-asserted-by":"publisher","DOI":"10.1086\/518026"},{"key":"e_1_2_3_53_1","doi-asserted-by":"publisher","DOI":"10.1515\/pac-2018-0608"},{"key":"e_1_2_3_54_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.5050087"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202216972","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202216972","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/anie.202216972","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202216972","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,17]],"date-time":"2023-08-17T11:30:19Z","timestamp":1692271819000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202216972"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,9]]},"references-count":56,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2023,2]]}},"alternative-id":["10.1002\/anie.202216972"],"URL":"https:\/\/doi.org\/10.1002\/anie.202216972","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,9]]},"assertion":[{"value":"2022-11-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-01-09","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202216972"}}