{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,2]],"date-time":"2026-11-02T10:14:11Z","timestamp":1793614451488,"version":"4.5.0"},"reference-count":71,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T00:00:00Z","timestamp":1675036800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,3,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A strongly twisted benzo\u2010fused tris\u2010cycloheptenylene, containing three dibenzosuberenone units fused to a common benzene ring, was subjected to Ramirez olefination and subsequent palladium\u2010catalyzed Suzuki\u2010Miyaura cross\u2010coupling with 4\u2010substituted phenylboronic acids. The high steric demand within the overcrowded, benzene\u2010rich benzo\u2010fused tris\u2010cycloheptenylenes enforced an unprecedented 1,2\u2010rearrangement upon \u03c0\u2010extension during the Suzuki coupling reaction. According to crystal structure analysis, the resulting negatively curved polycyclic aromatic hydrocarbons consist of two heptagons and one octagon surrounding a central benzene ring as a result of strain release. In the solid state, the materials exhibit a blue to blue\u2010green fluorescence with increased quantum yields and a hypsochromic shift of the emission maxima compared to their respective solutions.<\/jats:p>","DOI":"10.1002\/chem.202203735","type":"journal-article","created":{"date-parts":[[2023,1,5]],"date-time":"2023-01-05T05:41:42Z","timestamp":1672897302000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Ring\u2010Expanding Rearrangement of Benzo\u2010Fused Tris\u2010Cycloheptenylenes towards Nonplanar Polycyclic Aromatic Hydrocarbons"],"prefix":"10.1002","volume":"29","author":[{"given":"Barbara","family":"Ejlli","sequence":"first","affiliation":[{"name":"Max Planck Institute for Polymer Research  Ackermannweg 10 55128 Mainz Germany"},{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frank","family":"Rominger","sequence":"additional","affiliation":[{"name":"Organisch-Chemisches Institut Ruprecht-Karls-Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"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"},{"name":"InnovationLab  Speyerer Strasse 4 69115 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"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  Im Neuenheimer Feld 225 69120 Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6630-8786","authenticated-orcid":false,"given":"Klaus","family":"M\u00fcllen","sequence":"additional","affiliation":[{"name":"Max Planck Institute for Polymer Research  Ackermannweg 10 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,1,30]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202100260"},{"key":"e_1_2_8_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202100260"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c05504"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b04718"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC05586K"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00140"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201303875"},{"key":"e_1_2_8_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201303875"},{"key":"e_1_2_8_8_1","unstructured":"\u00a0"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00183H"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/352762a0"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9460000456"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carbon.2014.04.077"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/355333a0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00623J"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7QM00593H"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202201554"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201908643"},{"key":"e_1_2_8_18_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908643"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/nnano.2014.166"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00362a025"},{"key":"e_1_2_8_21_1","unstructured":"\u00a0"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00477"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00714"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05820"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b09992"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c12116"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1704"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202116955"},{"key":"e_1_2_8_29_1","unstructured":"\u00a0"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711437"},{"key":"e_1_2_8_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711437"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b03910"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b00403"},{"key":"e_1_2_8_33_1","unstructured":"\u00a0"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC02895K"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201902529"},{"key":"e_1_2_8_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201902529"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c03498"},{"key":"e_1_2_8_37_1","unstructured":"\u00a0"},{"key":"e_1_2_8_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01341"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201704008"},{"key":"e_1_2_8_40_1","unstructured":"\u00a0"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3027752"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201915327"},{"key":"e_1_2_8_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201915327"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202103530"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c01725"},{"key":"e_1_2_8_45_1","unstructured":"\u00a0"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja039389r"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00066"},{"key":"e_1_2_8_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(86)80661-3"},{"key":"e_1_2_8_49_1","unstructured":"\u00a0"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC02325E"},{"key":"e_1_2_8_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3054354"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201500560"},{"key":"e_1_2_8_53_1","unstructured":"\u201cPolycyclische aromatische Kohlenwasserstoffe mit multiplen [8] und [7]Annuleneinheiten\u201c B. Ejlli Dissertation University of Heidelberg (Germany) 2022."},{"key":"e_1_2_8_54_1","unstructured":"\u00a0"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106233"},{"key":"e_1_2_8_55_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202106233"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91109-8"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00006a039"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.9.207"},{"key":"e_1_2_8_59_1","unstructured":"Note that in this case (R=H) the separation from the fivefold coupling product and thus complete purification (even after variation of the purification methods) could not be achieved. The inseparable mixture was employed for characterization."},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0269082"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.202008071"},{"key":"e_1_2_8_62_1","unstructured":"B. Ejlli F. Rominger J. Freudenberg U.\u2005H.\u2005F. Bunz K. Muellen CSD Communication2021 CCDC 2116878."},{"key":"e_1_2_8_63_1","unstructured":"B. Ejlli F. Rominger J. Freudenberg U.\u2005H.\u2005F. Bunz K. Muellen CSD Communication2021 CCDC 2116879."},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29750000712"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203735","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202203735","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203735","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:42:27Z","timestamp":1760290947000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202203735"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,30]]},"references-count":71,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2023,3,13]]}},"alternative-id":["10.1002\/chem.202203735"],"URL":"https:\/\/doi.org\/10.1002\/chem.202203735","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,30]]},"assertion":[{"value":"2022-11-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-01-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202203735"}}