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Article: Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons

TitleUnexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons
Authors
Issue Date2016
Citation
Journal of the American Chemical Society, 2016, v. 138, n. 8, p. 2602-2608 How to Cite?
Abstract© 2016 American Chemical Society. Cyclodehydrogenation is a versatile reaction that has enabled the syntheses of numerous polycyclic aromatic hydrocarbons (PAHs). We now describe a unique Scholl reaction of 6,7,13,14-tetraarylbenzo[k]tetraphene, which "unexpectedly" forms five-membered rings accompanying highly selective 1,2-shift of aryl groups. The geometric and optoelectronic nature of the resulting bistetracene analogue with five-membered rings is comprehensively investigated by single-crystal X-ray, NMR, UV-vis absorption, and cyclic voltammetry analyses. Furthermore, a possible mechanism is proposed to account for the selective five-membered-ring formation with the rearrangement of the aryl groups, which can be rationalized by density functional theory (DFT) calculations. The theoretical results suggest that the formation of the bistetracene analogue with five-membered rings is kinetically controlled while an "expected" product with six-membered rings is thermodynamically more favored. These experimental and theoretical results provide further insights into the still controversial mechanism of the Scholl reaction as well as open up an unprecedented entry to extend the variety of PAHs by programing otherwise unpredictable rearrangements during the Scholl reaction.
Persistent Identifierhttp://hdl.handle.net/10722/276719
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, Junzhi-
dc.contributor.authorNarita, Akimitsu-
dc.contributor.authorOsella, Silvio-
dc.contributor.authorZhang, Wen-
dc.contributor.authorSchollmeyer, Dieter-
dc.contributor.authorBeljonne, David-
dc.contributor.authorFeng, Xinliang-
dc.contributor.authorMüllen, Klaus-
dc.date.accessioned2019-09-18T08:34:26Z-
dc.date.available2019-09-18T08:34:26Z-
dc.date.issued2016-
dc.identifier.citationJournal of the American Chemical Society, 2016, v. 138, n. 8, p. 2602-2608-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/276719-
dc.description.abstract© 2016 American Chemical Society. Cyclodehydrogenation is a versatile reaction that has enabled the syntheses of numerous polycyclic aromatic hydrocarbons (PAHs). We now describe a unique Scholl reaction of 6,7,13,14-tetraarylbenzo[k]tetraphene, which "unexpectedly" forms five-membered rings accompanying highly selective 1,2-shift of aryl groups. The geometric and optoelectronic nature of the resulting bistetracene analogue with five-membered rings is comprehensively investigated by single-crystal X-ray, NMR, UV-vis absorption, and cyclic voltammetry analyses. Furthermore, a possible mechanism is proposed to account for the selective five-membered-ring formation with the rearrangement of the aryl groups, which can be rationalized by density functional theory (DFT) calculations. The theoretical results suggest that the formation of the bistetracene analogue with five-membered rings is kinetically controlled while an "expected" product with six-membered rings is thermodynamically more favored. These experimental and theoretical results provide further insights into the still controversial mechanism of the Scholl reaction as well as open up an unprecedented entry to extend the variety of PAHs by programing otherwise unpredictable rearrangements during the Scholl reaction.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleUnexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.5b10399-
dc.identifier.scopuseid_2-s2.0-84960192639-
dc.identifier.volume138-
dc.identifier.issue8-
dc.identifier.spage2602-
dc.identifier.epage2608-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000371453700031-
dc.identifier.issnl0002-7863-

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