{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T05:37:07Z","timestamp":1788413827682,"version":"build-2803163510"},"reference-count":44,"publisher":"Wiley","issue":"45","license":[{"start":{"date-parts":[[2024,7,11]],"date-time":"2024-07-11T00:00:00Z","timestamp":1720656000000},"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":[[2024,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Kekulene, a cycloarene composed of 12 fused benzene rings in a circular arrangement, exhibits a highly planar and robust structure. Kekulene has been the subject of investigation into its aromaticity and electronic structure, particularly in relation to the cyclic benzenoid. We have successfully synthesized novel bowl\u2010shaped kekulene analogues with five\u2010membered rings incorporated into the kekulene structure. The results of DFT calculations and VT\u2010NMR spectra indicate that inversion of their concave\u2010convex structures occurs at room temperature. The NICS and AICD plots predict that the Clar's type resonance structure is found in a manner analogous to the pristine kekulene, albeit with the interruption of the \u03c0\u2010conjugation on the sp<jats:sup>3<\/jats:sup> carbons at the five\u2010membered rings. Despite the presence of the Clar's resonance structure, the Diels\u2010Alder reaction proceeded smoothly with a dienophile, in contrast to the behavior of planar kekulene derivatives. This study will lead to the creation of novel bowl\u2010shaped compounds and development of reactivity in aromatic compounds.<\/jats:p>","DOI":"10.1002\/chem.202401828","type":"journal-article","created":{"date-parts":[[2024,5,31]],"date-time":"2024-05-31T04:35:11Z","timestamp":1717130111000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Bowl\u2010Shaped Kekulene Analogues: Cycloarenes with two Five\u2010Membered Rings"],"prefix":"10.1002","volume":"30","author":[{"given":"Hideyuki","family":"Murakami","sequence":"first","affiliation":[{"name":"Department of Physical Science and Materials Engineering Iwate University  4-3-5 Ueda Morioka 020-8551 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroki","family":"Iwabuchi","sequence":"additional","affiliation":[{"name":"Department of Physical Science and Materials Engineering Iwate University  4-3-5 Ueda Morioka 020-8551 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miki","family":"Asari","sequence":"additional","affiliation":[{"name":"Department of Physical Science and Materials Engineering Iwate University  4-3-5 Ueda Morioka 020-8551 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2138-5902","authenticated-orcid":false,"given":"Hiroko","family":"Yamada","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7948-8501","authenticated-orcid":false,"given":"Daiki","family":"Kuzuhara","sequence":"additional","affiliation":[{"name":"Department of Physical Science and Materials Engineering Iwate University  4-3-5 Ueda Morioka 020-8551 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,7,11]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19831161021"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1088\/0370-1298\/64\/10\/309"},{"key":"e_1_2_9_3_1","unstructured":"E. 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