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Article: Toward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene

TitleToward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene
Authors
Issue Date2018
Citation
Journal of the American Chemical Society, 2018, v. 140, n. 20, p. 6240-6244 How to Cite?
Abstract© 2018 American Chemical Society. Zigzag-edged nanographene with two rows of fused linear acenes, called as n-peri-acene (n-PA), is considered as a potential building unit in the arena of organic electronics. n-PAs with four (peri-tetracene, 4-PA), five (peri-pentacene, 5-PA) or more benzene rings in a row have been predicted to show open-shell character, which would be attractive for the development of unprecedented molecular spintronics. However, solution-based synthesis of open-shell n-PA has thus far not been successful because of the poor chemical stability. Herein we demonstrated the synthesis and characterization of the hitherto unknown 4-PA by a rational strategy in which steric protection of the zigzag edges playing a pivotal role. The obtained 4-PA possesses a singlet biradical character (y 0 = 72%) and exhibits remarkable persistent stability with a half-life time (t 1/2 ) of ∼3 h under ambient conditions. UV-vis-NIR and electrochemical measurements reveal a narrow optical/electrochemical energy gap (1.11 eV) for 4-PA. Moreover, the bay regions of 4-PA enable the efficient 2-fold Diels-Alder reaction, yielding a novel full zigzag-edged circumanthracene.
Persistent Identifierhttp://hdl.handle.net/10722/276591
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAjayakumar, M. R.-
dc.contributor.authorFu, Yubin-
dc.contributor.authorMa, Ji-
dc.contributor.authorHennersdorf, Felix-
dc.contributor.authorKomber, Hartmut-
dc.contributor.authorWeigand, Jan J.-
dc.contributor.authorAlfonsov, Alexey-
dc.contributor.authorPopov, Alexey A.-
dc.contributor.authorBerger, Reinhard-
dc.contributor.authorLiu, Junzhi-
dc.contributor.authorMüllen, Klaus-
dc.contributor.authorFeng, Xinliang-
dc.date.accessioned2019-09-18T08:34:04Z-
dc.date.available2019-09-18T08:34:04Z-
dc.date.issued2018-
dc.identifier.citationJournal of the American Chemical Society, 2018, v. 140, n. 20, p. 6240-6244-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/276591-
dc.description.abstract© 2018 American Chemical Society. Zigzag-edged nanographene with two rows of fused linear acenes, called as n-peri-acene (n-PA), is considered as a potential building unit in the arena of organic electronics. n-PAs with four (peri-tetracene, 4-PA), five (peri-pentacene, 5-PA) or more benzene rings in a row have been predicted to show open-shell character, which would be attractive for the development of unprecedented molecular spintronics. However, solution-based synthesis of open-shell n-PA has thus far not been successful because of the poor chemical stability. Herein we demonstrated the synthesis and characterization of the hitherto unknown 4-PA by a rational strategy in which steric protection of the zigzag edges playing a pivotal role. The obtained 4-PA possesses a singlet biradical character (y 0 = 72%) and exhibits remarkable persistent stability with a half-life time (t 1/2 ) of ∼3 h under ambient conditions. UV-vis-NIR and electrochemical measurements reveal a narrow optical/electrochemical energy gap (1.11 eV) for 4-PA. Moreover, the bay regions of 4-PA enable the efficient 2-fold Diels-Alder reaction, yielding a novel full zigzag-edged circumanthracene.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleToward Full Zigzag-Edged Nanographenes: Peri-Tetracene and Its Corresponding Circumanthracene-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.8b03711-
dc.identifier.scopuseid_2-s2.0-85047098575-
dc.identifier.volume140-
dc.identifier.issue20-
dc.identifier.spage6240-
dc.identifier.epage6244-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000433404000013-
dc.identifier.issnl0002-7863-

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