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Article: Helical Nanographenes Containing an Azulene Unit: Synthesis, Crystal Structures, and Properties

TitleHelical Nanographenes Containing an Azulene Unit: Synthesis, Crystal Structures, and Properties
Authors
Keywordsazulene
helicenes
nanographenes
polycyclic aromatic hydrocarbons
Scholl reaction
Issue Date2020
PublisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home
Citation
Angewandte Chemie (International Edition), 2020, v. 59 n. 14, p. 5637-5642 How to Cite?
AbstractThree unprecedented helical nanographenes (1 , 2 , and 3 ) containing an azulene unit are synthesized. The resultant helical structures are unambiguously confirmed by X‐ray crystallographic analysis. The embedded azulene unit in 2 possesses a record‐high twisting degree (16.1°) as a result of the contiguous steric repulsion at the helical inner rim. Structural analysis in combination with theoretical calculations reveals that these helical nanographenes manifest a global aromatic structure, while the inner azulene unit exhibits weak antiaromatic character. Furthermore, UV/Vis‐spectral measurements reveal that superhelicenes 2 and 3 possess narrow energy gaps (2 : 1.88 eV; 3 : 2.03 eV), as corroborated by cyclic voltammetry and supported by density functional theory (DFT) calculations. The stable oxidized and reduced states of 2 and 3 are characterized by in‐situ EPR/Vis–NIR spectroelectrochemistry. Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated structures and physical properties.
Persistent Identifierhttp://hdl.handle.net/10722/284790
ISSN
2023 Impact Factor: 16.1
2023 SCImago Journal Rankings: 5.300
PubMed Central ID
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorMa, J-
dc.contributor.authorFu, Y-
dc.contributor.authorDmitrieva, E-
dc.contributor.authorLiu, F-
dc.contributor.authorKomber, H-
dc.contributor.authorHennersdorf, F-
dc.contributor.authorPopov, A-
dc.contributor.authorWeigand, J-
dc.contributor.authorLiu, J-
dc.contributor.authorFeng, X-
dc.date.accessioned2020-08-07T09:02:39Z-
dc.date.available2020-08-07T09:02:39Z-
dc.date.issued2020-
dc.identifier.citationAngewandte Chemie (International Edition), 2020, v. 59 n. 14, p. 5637-5642-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/284790-
dc.description.abstractThree unprecedented helical nanographenes (1 , 2 , and 3 ) containing an azulene unit are synthesized. The resultant helical structures are unambiguously confirmed by X‐ray crystallographic analysis. The embedded azulene unit in 2 possesses a record‐high twisting degree (16.1°) as a result of the contiguous steric repulsion at the helical inner rim. Structural analysis in combination with theoretical calculations reveals that these helical nanographenes manifest a global aromatic structure, while the inner azulene unit exhibits weak antiaromatic character. Furthermore, UV/Vis‐spectral measurements reveal that superhelicenes 2 and 3 possess narrow energy gaps (2 : 1.88 eV; 3 : 2.03 eV), as corroborated by cyclic voltammetry and supported by density functional theory (DFT) calculations. The stable oxidized and reduced states of 2 and 3 are characterized by in‐situ EPR/Vis–NIR spectroelectrochemistry. Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated structures and physical properties.-
dc.languageeng-
dc.publisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www3.interscience.wiley.com/journal/26737/home-
dc.relation.ispartofAngewandte Chemie (International Edition)-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subjectazulene-
dc.subjecthelicenes-
dc.subjectnanographenes-
dc.subjectpolycyclic aromatic hydrocarbons-
dc.subjectScholl reaction-
dc.titleHelical Nanographenes Containing an Azulene Unit: Synthesis, Crystal Structures, and Properties-
dc.typeArticle-
dc.identifier.emailLiu, J: juliu@hku.hk-
dc.identifier.authorityLiu, J=rp02584-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1002/anie.201914716-
dc.identifier.pmid31867754-
dc.identifier.pmcidPMC7155134-
dc.identifier.scopuseid_2-s2.0-85078989062-
dc.identifier.hkuros311686-
dc.identifier.volume59-
dc.identifier.issue14-
dc.identifier.spage5637-
dc.identifier.epage5642-
dc.identifier.isiWOS:000510558800001-
dc.publisher.placeGermany-
dc.identifier.issnl1433-7851-

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