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Article: Synthesis of a Dicyclohepta[a,g]heptalene-Containing Polycyclic Conjugated Hydrocarbon and the Impact of Non-Alternant Topologies

TitleSynthesis of a Dicyclohepta[<i>a</i>,<i>g</i>]heptalene-Containing Polycyclic Conjugated Hydrocarbon and the Impact of Non-Alternant Topologies
Authors
KeywordsAntiaromaticity
Four Contiguous Heptagons
Non-Alternant Topology
Polycyclic Conjugated Hydrocarbons (PCHs)
Issue Date10-Jan-2023
PublisherWiley
Citation
Angewandte Chemie International Edition, 2023, v. 62, n. 10 How to Cite?
Abstract

Incorporating non-hexagonal rings into polycyclic conjugated hydrocarbons (PCHs) can significantly affect their electronic and optoelectronic properties and chemical reactivities. Here, we report the first bottom-up synthesis of a dicyclohepta[a,g]heptalene-embedded PCH (1) with four continuous heptagons, which are arranged in a "Z" shape. Compared with its structural isomer bischrysene 1 R with only hexagonal rings, compound 1 presents a distinct antiaromatic character, especially the inner heptalene core, which possesses clear antiaromatic nature. In addition, PCH 1 exhibits a narrower highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap than its benzenoid contrast 1 R, as verified by experimental measurements and theoretical calculations. Our work reported herein not only provides a new way to synthesize novel PCHs with non-alternant topologies but also offers the possibility to tune their electronic and optical properties.


Persistent Identifierhttp://hdl.handle.net/10722/338492
ISSN
2023 Impact Factor: 16.1
2023 SCImago Journal Rankings: 5.300
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWang, JT-
dc.contributor.authorGámez, FG-
dc.contributor.authorMarín-Beloqui, J-
dc.contributor.authorDiaz-Andres, A-
dc.contributor.authorMiao, XH-
dc.contributor.authorCasanova, D-
dc.contributor.authorCasado, J-
dc.contributor.authorLiu, JZ-
dc.date.accessioned2024-03-11T10:29:18Z-
dc.date.available2024-03-11T10:29:18Z-
dc.date.issued2023-01-10-
dc.identifier.citationAngewandte Chemie International Edition, 2023, v. 62, n. 10-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/338492-
dc.description.abstract<p>Incorporating non-hexagonal rings into polycyclic conjugated hydrocarbons (PCHs) can significantly affect their electronic and optoelectronic properties and chemical reactivities. Here, we report the first bottom-up synthesis of a dicyclohepta[a,g]heptalene-embedded PCH (1) with four continuous heptagons, which are arranged in a "Z" shape. Compared with its structural isomer bischrysene 1 R with only hexagonal rings, compound 1 presents a distinct antiaromatic character, especially the inner heptalene core, which possesses clear antiaromatic nature. In addition, PCH 1 exhibits a narrower highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap than its benzenoid contrast 1 R, as verified by experimental measurements and theoretical calculations. Our work reported herein not only provides a new way to synthesize novel PCHs with non-alternant topologies but also offers the possibility to tune their electronic and optical properties.</p>-
dc.languageeng-
dc.publisherWiley-
dc.relation.ispartofAngewandte Chemie International Edition-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subjectAntiaromaticity-
dc.subjectFour Contiguous Heptagons-
dc.subjectNon-Alternant Topology-
dc.subjectPolycyclic Conjugated Hydrocarbons (PCHs)-
dc.titleSynthesis of a Dicyclohepta[<i>a</i>,<i>g</i>]heptalene-Containing Polycyclic Conjugated Hydrocarbon and the Impact of Non-Alternant Topologies-
dc.typeArticle-
dc.identifier.doi10.1002/anie.202217124-
dc.identifier.pmid36511094-
dc.identifier.scopuseid_2-s2.0-85145934352-
dc.identifier.volume62-
dc.identifier.issue10-
dc.identifier.eissn1521-3773-
dc.identifier.isiWOS:000911095600001-
dc.publisher.placeWEINHEIM-
dc.identifier.issnl1433-7851-

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