Tuning aromaticity of cyclocarbons by heteroatom doping

Tuning aromaticity of cyclocarbons by heteroatom doping | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Physical Sciences - Article Tuning aromaticity of cyclocarbons by heteroatom doping Luye Sun, Yuan Guo, Ihor Sahalianov, Zheng Zhou, Wei Zheng, Wenzhi Xiang, and 7 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-5208561/v2 This work is licensed under a CC BY 4.0 License Status: Posted Version 2 posted You are reading this latest preprint version Show more versions Abstract Cyclo[ n ]carbons (C n ) have sparked substantial interest among experimentalists and theoreticians owing to their elusive geometric structures and unique aromaticity. Composed of two-coordinated sp-hybridized carbon atoms, C n thus forms two perpendicular conjugated π-electron systems, i.e., out-of-plane and in-plane. Till now, on-surface generated cyclocarbons are either doubly aromatic or doubly anti-aromatic, as the number of electrons within out-of-plane and in-plane π systems was equal. Doping with heteroatoms allows one to create two π systems with different numbers of electrons, and to tune the aromaticity. Herein, we successfully generated two heteroatom-doped cyclocarbons, C 12 S and C 12 N, and characterized their chemical and electronic structures. Calculations show that C 12 S exhibits out-of-plane (14 e ) aromatic and in-plane (12 e ) anti-aromatic character, resulting in a total non-aromaticity. For C 12 N, the out-of-plane (14 e ) aromatic and in-plane (13 e ) non-aromatic characters lead to a total aromaticity. Doping with heteroatoms may open up the field of aromaticity engineering within cyclocarbons. Physical sciences/Chemistry/Physical chemistry/Chemical physics Physical sciences/Chemistry/Surface chemistry/Scanning probe microscopy Full Text Additional Declarations The authors declare no competing interests. Supplementary Files supportinginformation.pdf supporting information Cite Share Download PDF Status: Posted Version 2 posted You are reading this latest preprint version Show more versions Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-5208561","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Physical Sciences - Article","associatedPublications":[],"authors":[{"id":364970068,"identity":"3168c9ee-4b6b-4ae8-95dd-e0afcf84bfd9","order_by":0,"name":"Luye Sun","email":"","orcid":"","institution":"Tongji University","correspondingAuthor":false,"prefix":"","firstName":"Luye","middleName":"","lastName":"Sun","suffix":""},{"id":364970069,"identity":"32e5dcb2-71fd-4b61-a35f-9cceba7e80d7","order_by":1,"name":"Yuan Guo","email":"","orcid":"","institution":"Tongji 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doping","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":true,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research 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Composed of two-coordinated sp-hybridized carbon atoms, C\u003csub\u003e\u003cem\u003en\u003c/em\u003e\u003c/sub\u003e thus forms two perpendicular conjugated π-electron systems, i.e., out-of-plane and in-plane. Till now, on-surface generated cyclocarbons are either doubly aromatic or doubly anti-aromatic, as the number of electrons within out-of-plane and in-plane π systems was equal. Doping with heteroatoms allows one to create two π systems with different numbers of electrons, and to tune the aromaticity. Herein, we successfully generated two heteroatom-doped cyclocarbons, C\u003csub\u003e12\u003c/sub\u003eS and C\u003csub\u003e12\u003c/sub\u003eN, and characterized their chemical and electronic structures. Calculations show that C\u003csub\u003e12\u003c/sub\u003eS exhibits out-of-plane (14 \u003cem\u003ee\u003c/em\u003e) aromatic and in-plane (12 \u003cem\u003ee\u003c/em\u003e) anti-aromatic character, resulting in a total non-aromaticity. For C\u003csub\u003e12\u003c/sub\u003eN, the out-of-plane (14 \u003cem\u003ee\u003c/em\u003e) aromatic and in-plane (13 \u003cem\u003ee\u003c/em\u003e) non-aromatic characters lead to a total aromaticity. 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