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Article: Curved π-conjugated corannulene dimer diradicaloids

TitleCurved π-conjugated corannulene dimer diradicaloids
Authors
Issue Date2018
Citation
Chemical Science, 2018, v. 9, n. 22, p. 5100-5105 How to Cite?
AbstractSo far, most reported open-shell singlet diradicaloids are based on planar π-conjugated molecules. Herein, we report the bridged corannulene dimer diradicaloids, Cor-D1 and Cor-D2, both showing a three-dimensional curved π-conjugated structure. Cor-D1 has a small diradical character (y0 = 5.4%) and behaves more like a closed-shell quinoidal compound at room temperature, while Cor-D2 is a typical open-shell diradicaloid with a larger diradical character (y0 = 16.9%). Both compounds exhibited paramagnetic activity at elevated temperatures, with a singlet-triplet energy gap (ΔES-T) of -8.4 and -3.0 kcal mol-1, respectively. X-ray crystallographic analysis revealed that both molecules have a dumbbell-shaped geometry, with the two terminal corannulene bowls bent to opposite directions. The spin is largely delocalized onto the two bowls in Cor-D2 and there are multiple [CH⋯π] interactions between the neighboring bowls. Chemical oxidation/reduction to their respective dications/dianions results in global aromaticity with [4n + 2] π-electrons delocalized through the periphery of the whole framework.
Persistent Identifierhttp://hdl.handle.net/10722/341226
ISSN
2023 Impact Factor: 7.6
2023 SCImago Journal Rankings: 2.333
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWang, Qing-
dc.contributor.authorHu, Pan-
dc.contributor.authorTanaka, Takayuki-
dc.contributor.authorGopalakrishna, Tullimilli Y.-
dc.contributor.authorHerng, Tun Seng-
dc.contributor.authorPhan, Hoa-
dc.contributor.authorZeng, Wangdong-
dc.contributor.authorDing, Jun-
dc.contributor.authorOsuka, Atsuhiro-
dc.contributor.authorChi, Chunyan-
dc.contributor.authorSiegel, Jay-
dc.contributor.authorWu, Jishan-
dc.date.accessioned2024-03-13T08:41:09Z-
dc.date.available2024-03-13T08:41:09Z-
dc.date.issued2018-
dc.identifier.citationChemical Science, 2018, v. 9, n. 22, p. 5100-5105-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10722/341226-
dc.description.abstractSo far, most reported open-shell singlet diradicaloids are based on planar π-conjugated molecules. Herein, we report the bridged corannulene dimer diradicaloids, Cor-D1 and Cor-D2, both showing a three-dimensional curved π-conjugated structure. Cor-D1 has a small diradical character (y0 = 5.4%) and behaves more like a closed-shell quinoidal compound at room temperature, while Cor-D2 is a typical open-shell diradicaloid with a larger diradical character (y0 = 16.9%). Both compounds exhibited paramagnetic activity at elevated temperatures, with a singlet-triplet energy gap (ΔES-T) of -8.4 and -3.0 kcal mol-1, respectively. X-ray crystallographic analysis revealed that both molecules have a dumbbell-shaped geometry, with the two terminal corannulene bowls bent to opposite directions. The spin is largely delocalized onto the two bowls in Cor-D2 and there are multiple [CH⋯π] interactions between the neighboring bowls. Chemical oxidation/reduction to their respective dications/dianions results in global aromaticity with [4n + 2] π-electrons delocalized through the periphery of the whole framework.-
dc.languageeng-
dc.relation.ispartofChemical Science-
dc.titleCurved π-conjugated corannulene dimer diradicaloids-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c8sc01388h-
dc.identifier.scopuseid_2-s2.0-85048186908-
dc.identifier.volume9-
dc.identifier.issue22-
dc.identifier.spage5100-
dc.identifier.epage5105-
dc.identifier.eissn2041-6539-
dc.identifier.isiWOS:000434693300023-

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