{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:47:38Z","timestamp":1760316458169,"version":"build-2065373602"},"reference-count":55,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2021,5,27]],"date-time":"2021-05-27T00:00:00Z","timestamp":1622073600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["SFB1249"],"award-info":[{"award-number":["SFB1249"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004350","name":"Studienstiftung des Deutschen Volkes","doi-asserted-by":"publisher","award":["PhD scholarship"],"award-info":[{"award-number":["PhD scholarship"]}],"id":[{"id":"10.13039\/501100004350","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":[[2021,7,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki\u2010coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel\u2010Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS\u2010ethynyl)\u2010substituted naphtha[1,8\u2010<jats:italic>gh<\/jats:italic>:5,4\u2010<jats:italic>g<\/jats:italic>\u2032<jats:italic>h<\/jats:italic>\u2032]diquinoline and naphtho[1,8\u2010<jats:italic>bc<\/jats:italic>:5,4\u2010<jats:italic>b<\/jats:italic>\u2032<jats:italic>c<\/jats:italic>\u2032]diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs.<\/jats:p>","DOI":"10.1002\/chem.202101246","type":"journal-article","created":{"date-parts":[[2021,5,2]],"date-time":"2021-05-02T22:10:53Z","timestamp":1619993453000},"page":"10569-10573","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["TIPS\u2010Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes"],"prefix":"10.1002","volume":"27","author":[{"given":"Lukas","family":"Ahrens","sequence":"first","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Steffen","family":"Maier","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erik","family":"Misselwitz","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas","family":"Oeser","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Frank","family":"Rominger","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0998-693X","authenticated-orcid":false,"given":"Jan","family":"Freudenberg","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9369-5387","authenticated-orcid":false,"given":"Uwe H. F.","family":"Bunz","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"},{"name":"Centre for Advanced Materials (CAM) Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 225 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,5,27]]},"reference":[{"unstructured":"\u00a0","key":"e_1_2_2_1_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_2_2","DOI":"10.1021\/cr050966z"},{"doi-asserted-by":"publisher","key":"e_1_2_2_3_2","DOI":"10.1002\/anie.200604045"},{"doi-asserted-by":"publisher","key":"e_1_2_2_3_3","DOI":"10.1002\/ange.200604045"},{"doi-asserted-by":"publisher","key":"e_1_2_2_4_1","DOI":"10.1063\/1.1511826"},{"doi-asserted-by":"publisher","key":"e_1_2_2_5_1","DOI":"10.1002\/asia.201402899"},{"unstructured":"\u00a0","key":"e_1_2_2_6_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_7_2","DOI":"10.1126\/science.1232994"},{"doi-asserted-by":"publisher","key":"e_1_2_2_8_2","DOI":"10.1038\/s41586-019-1339-4"},{"unstructured":"\u00a0","key":"e_1_2_2_9_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_10_2","DOI":"10.1021\/ar50004a002"},{"doi-asserted-by":"publisher","key":"e_1_2_2_11_2","DOI":"10.1021\/ar050191g"},{"doi-asserted-by":"publisher","key":"e_1_2_2_12_1","DOI":"10.1039\/C9TC04843J"},{"unstructured":"\u00a0","key":"e_1_2_2_13_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_14_2","DOI":"10.1021\/ja0162459"},{"doi-asserted-by":"publisher","key":"e_1_2_2_15_2","DOI":"10.1021\/ja051798v"},{"doi-asserted-by":"publisher","key":"e_1_2_2_16_1","DOI":"10.1021\/ja306056x"},{"doi-asserted-by":"publisher","key":"e_1_2_2_17_1","DOI":"10.1002\/anie.202015348"},{"doi-asserted-by":"publisher","key":"e_1_2_2_17_2","DOI":"10.1002\/ange.202015348"},{"unstructured":"\u00a0","key":"e_1_2_2_18_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_19_2","DOI":"10.1002\/chem.201801079"},{"doi-asserted-by":"publisher","key":"e_1_2_2_20_2","DOI":"10.1002\/anie.201909614"},{"doi-asserted-by":"publisher","key":"e_1_2_2_20_3","DOI":"10.1002\/ange.201909614"},{"doi-asserted-by":"publisher","key":"e_1_2_2_21_1","DOI":"10.1021\/ja503643s"},{"doi-asserted-by":"publisher","key":"e_1_2_2_22_1","DOI":"10.1039\/C6TC04365H"},{"doi-asserted-by":"publisher","key":"e_1_2_2_23_1","DOI":"10.1021\/ar500278w"},{"unstructured":"\u00a0","key":"e_1_2_2_24_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_25_2","DOI":"10.1021\/ja505240e"},{"doi-asserted-by":"publisher","key":"e_1_2_2_26_2","DOI":"10.1021\/acs.chemmater.6b02552"},{"doi-asserted-by":"publisher","key":"e_1_2_2_27_1","DOI":"10.1021\/cm503439r"},{"doi-asserted-by":"publisher","key":"e_1_2_2_28_1","DOI":"10.1021\/ja809659b"},{"doi-asserted-by":"publisher","key":"e_1_2_2_29_1","DOI":"10.1021\/acsami.5b00113"},{"unstructured":"\u00a0","key":"e_1_2_2_30_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_31_2","DOI":"10.1002\/chem.200900990"},{"doi-asserted-by":"publisher","key":"e_1_2_2_32_2","DOI":"10.1021\/acs.accounts.9b00160"},{"doi-asserted-by":"publisher","key":"e_1_2_2_33_2","DOI":"10.1055\/s-0031-1290323"},{"doi-asserted-by":"publisher","key":"e_1_2_2_34_2","DOI":"10.1002\/adma.201305497"},{"doi-asserted-by":"publisher","key":"e_1_2_2_35_1","DOI":"10.1039\/c1ob05454f"},{"doi-asserted-by":"publisher","key":"e_1_2_2_36_1","DOI":"10.1002\/chem.201303308"},{"doi-asserted-by":"publisher","key":"e_1_2_2_37_1","DOI":"10.1002\/chem.201903646"},{"doi-asserted-by":"publisher","key":"e_1_2_2_38_1","DOI":"10.1021\/jo00361a014"},{"unstructured":"Gaussian 16 Revision C.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A.\u2005V. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M.\u2005J. Bearpark J.\u2005J. Heyd E.\u2005N. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T.\u2005A. Keith R. Kobayashi J. Normand K. Raghavachari A.\u2005P. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman D.\u2005J. Fox Gaussian Inc. Wallingford CT 2016.","key":"e_1_2_2_39_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_40_1","DOI":"10.1002\/chem.202003999"},{"doi-asserted-by":"publisher","key":"e_1_2_2_41_1","DOI":"10.1002\/adma.201004554"},{"key":"e_1_2_2_42_1","first-page":"427","volume":"76","author":"Moliterni A.","year":"2020","journal-title":"Acta Cryst."},{"doi-asserted-by":"publisher","key":"e_1_2_2_43_1","DOI":"10.1107\/S0365110X65001494"},{"doi-asserted-by":"publisher","key":"e_1_2_2_44_1","DOI":"10.1063\/1.5043379"},{"unstructured":"\u00a0","key":"e_1_2_2_45_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_46_2","DOI":"10.1021\/jp0034426"},{"doi-asserted-by":"publisher","key":"e_1_2_2_47_2","DOI":"10.1021\/cr0300901"},{"doi-asserted-by":"publisher","key":"e_1_2_2_48_1","DOI":"10.1039\/c2tc00363e"},{"unstructured":"\u00a0","key":"e_1_2_2_49_1"},{"doi-asserted-by":"publisher","key":"e_1_2_2_50_2","DOI":"10.1016\/j.tet.2016.07.083"},{"doi-asserted-by":"publisher","key":"e_1_2_2_51_2","DOI":"10.1021\/ol702494k"},{"unstructured":"J. Yamamoto K. Kinpara Y. Fukuda Y. Nakasato K. Uchida T. Nishikawa (Kyowa Hakko Kirin Co. Ltd.) 2011 WO 2011093365.","key":"e_1_2_2_52_1"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202101246","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202101246","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202101246","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:27:31Z","timestamp":1760286451000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202101246"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,27]]},"references-count":55,"journal-issue":{"issue":"41","published-print":{"date-parts":[[2021,7,21]]}},"alternative-id":["10.1002\/chem.202101246"],"URL":"https:\/\/doi.org\/10.1002\/chem.202101246","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2021,5,27]]},"assertion":[{"value":"2021-04-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-05-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}