{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T12:46:15Z","timestamp":1792673175878,"version":"4.5.0"},"reference-count":39,"publisher":"American Chemical Society (ACS)","issue":"42","license":[{"start":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T00:00:00Z","timestamp":1787616000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-17-EURE-0009"],"award-info":[{"award-number":["ANR-17-EURE-0009"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["JPMXP1224NR5041"],"award-info":[{"award-number":["JPMXP1224NR5041"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["JPMXP1225NR5016"],"award-info":[{"award-number":["JPMXP1225NR5016"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004718","name":"Universit? de Toulouse","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004718","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["22H00325"],"award-info":[{"award-number":["22H00325"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["24KF0269"],"award-info":[{"award-number":["24KF0269"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["25H00422"],"award-info":[{"award-number":["25H00422"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["25K24715"],"award-info":[{"award-number":["25K24715"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP25KJ1768"],"award-info":[{"award-number":["JP25KJ1768"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004794","name":"Centre National de la Recherche Scientifique","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004496","name":"National Institute for Materials Science","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004496","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>On-surface synthesis has become a powerful technique for obtaining various nanostructures, mainly by linking small precursor molecules. In contrast, the cleavage of specific moieties from precursor molecules is also an important and promising strategy to increase the variety of products. Here, we report the on-surface synthesis of hexabenzocoronene (HBC) and its hexa-fluorinated analogue (6F-HBC) from the parent heptaphenylcycloheptatrienes, via the systematic extrusion of a phenyl-CH: carbenic fragment and a subsequent cyclodehydrogenation process on a Au(111) substrate. Their structures and electronic properties were investigated in-depth by low-temperature scanning tunneling microscopy with a CO-terminated tip. Annealing at 200 \u00b0C triggers the elimination of the phenylcarbenic groups from the cycloheptatriene core, resulting in the formation of both hexaphenylbenzene and its fluorinated analogue. Although the former was transformed into HBC via cyclodehydrogenation at 300 \u00b0C, the fluorinated one was thermally desorbed from the surface even at 250 \u00b0C. We found that depositing fluorinated heptaphenylcycloheptatriene onto the substrate kept at 300 \u00b0C successfully yielded 6F-HBC. The influence of fluorine substitution was identified through molecular assemblies and bond-resolved images as well as dI\/dV measurements, all obtained using the same CO-terminated tip. Our findings demonstrate that the retro-Bu\u0308chner reaction, corresponding to a ring contraction, is an effective strategy to enhance the variety of structures and electronic properties of on-surface synthesized products.<\/jats:p>","DOI":"10.1021\/acs.jpclett.6c01675","type":"journal-article","created":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T03:58:25Z","timestamp":1788235105000},"page":"12171-12178","source":"Crossref","is-referenced-by-count":0,"title":["On-Surface Synthesis\nof Hexabenzocoronenes via a Retro-Bu\u0308chner\nReaction of Heptaarylcycloheptatrienes"],"prefix":"10.1021","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2128-0120","authenticated-orcid":true,"given":"Shigeki","family":"Kawai","sequence":"first","affiliation":[{"name":"National Institute for Materials Science , , 1-2-1 Sengen , , ,","place":["Tsukuba, Ibaraki, Japan, 305-0047"]},{"name":"University of Tsukuba , , , ,","place":["Tsukuba, Ibaraki, Japan, 305-8571"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haruka","family":"Tsuji","sequence":"additional","affiliation":[{"name":"National Institute for Materials Science , , 1-2-1 Sengen , , ,","place":["Tsukuba, Ibaraki, Japan, 305-0047"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donglin","family":"Li","sequence":"additional","affiliation":[{"name":"National Institute for Materials Science , , 1-2-1 Sengen , , ,","place":["Tsukuba, Ibaraki, Japan, 305-0047"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pranshu","family":"Pal","sequence":"additional","affiliation":[{"name":"National Institute of Technology Srinagar , , Hazratbal, , ,","place":["Srinagar, Jammu and Kashmir, India, 190006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7931-603X","authenticated-orcid":true,"given":"Oscar","family":"Custance","sequence":"additional","affiliation":[{"name":"National Institute for Materials Science , , 1-2-1 Sengen , , ,","place":["Tsukuba, Ibaraki, Japan, 305-0047"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3746-6803","authenticated-orcid":true,"given":"Toshikaze","family":"Kariyado","sequence":"additional","affiliation":[{"name":"National Institute for Materials Science , , 1-1 Namiki , , ,","place":["Tsukuba, Ibaraki, Japan, 305-0044"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yorie","family":"Ohno","sequence":"additional","affiliation":[{"name":"Nara Institute of Science and Technology , , 8916-5 Takayama , , ,","place":["Ikoma, Nara, Japan, 630-0192"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9281-0403","authenticated-orcid":true,"given":"Yohei","family":"Hattori","sequence":"additional","affiliation":[{"name":"Nara Institute of Science and Technology , , 8916-5 Takayama , , ,","place":["Ikoma, Nara, Japan, 630-0192"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas A.","family":"Hector","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Toulouse, CNRS, CEMES , 29 Rue Marvig , ,","place":["Toulouse, France, 31055"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5292-5975","authenticated-orcid":true,"given":"Claire","family":"Kammerer","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Toulouse, CNRS, CEMES , 29 Rue Marvig , ,","place":["Toulouse, France, 31055"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4993-4213","authenticated-orcid":true,"given":"Gwe\u0301nae\u0308l","family":"Rapenne","sequence":"additional","affiliation":[{"name":"Nara Institute of Science and Technology , , 8916-5 Takayama , , ,","place":["Ikoma, Nara, Japan, 630-0192"]},{"name":"Universite\u0301 de Toulouse, CNRS, CEMES , 29 Rue Marvig , ,","place":["Toulouse, France, 31055"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,25]]},"reference":[{"key":"2026102208022643400_cit1","doi-asserted-by":"publisher","first-page":"264","DOI":"10.1021\/jo01084a635","article-title":"Synthesis\nof cycloheptatriene","volume":"24","author":"Winberg","year":"1959","journal-title":"J. Org. Chem."},{"key":"2026102208022643400_cit2","doi-asserted-by":"publisher","first-page":"3203","DOI":"10.1021\/ja01641a027","article-title":"The cycloheptatrienylium (tropylium)\nion","volume":"76","author":"Von E. Doering","year":"1954","journal-title":"J. Am. Chem. Soc."},{"key":"2026102208022643400_cit3","doi-asserted-by":"publisher","first-page":"2377","DOI":"10.1002\/cber.188501802119","article-title":"Uber die einwirkung\nvon diazoessigather auf aromatisch\nkohlenwasserstoffe","volume":"18","author":"Bu\u0308chner","year":"1885","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"2026102208022643400_cit4","doi-asserted-by":"publisher","first-page":"873","DOI":"10.1021\/jo00318a010","article-title":"Transition-Metal-Catalyzed\nReactions of Diazo Compounds.\n2. Addition to Aromatic Molecules: Catalysis of Buchner\u2019s Synthesis\nof Cycloheptatrienes","volume":"46","author":"Anciaux","year":"1981","journal-title":"J. Org. Chem."},{"issue":"17","key":"2026102208022643400_cit5","doi-asserted-by":"publisher","first-page":"2437","DOI":"10.1055\/s-0031-1289520","article-title":"Bu\u0308chner\nand Beyond: Arene\nCyclopropanation as Applied to Natural Product Total Synthesis","volume":"2011","author":"Reisman","year":"2011","journal-title":"Synlett"},{"key":"2026102208022643400_cit6","doi-asserted-by":"publisher","first-page":"4717","DOI":"10.1021\/acs.chemrev.8b00601","article-title":"Controlling\na Chemical Coupling Reaction on a Surface:\nTools and Strategies for On-Surface Synthesis","volume":"119","author":"Clair","year":"2019","journal-title":"Chem. Rev."},{"key":"2026102208022643400_cit7","doi-asserted-by":"publisher","first-page":"687","DOI":"10.1038\/nnano.2007.346","article-title":"Nano-Architectures by Covalent Assembly of Molecular Building Blocks","volume":"2","author":"Grill","year":"2007","journal-title":"Nat. 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Chem."},{"key":"2026102208022643400_cit10","doi-asserted-by":"publisher","first-page":"470","DOI":"10.1038\/nature09211","article-title":"Atomically Precise Bottom-Up Fabrication\nof Graphene Nanoribbons","volume":"466","author":"Cai","year":"2010","journal-title":"Nature"},{"key":"2026102208022643400_cit11","doi-asserted-by":"publisher","first-page":"4024","DOI":"10.1002\/anie.201208597","article-title":"Glaser Coupling at\nMetal Surfaces","volume":"52","author":"Gao","year":"2013","journal-title":"Angew. Chem.,\nInt. 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Chem., Int.\nEd."},{"issue":"2","key":"2026102208022643400_cit15","doi-asserted-by":"publisher","first-page":"1563","DOI":"10.1021\/jacs.3c11652","article-title":"Highly Selective On-Surface Ring-Opening\nof Aromatic Azulene Moiety","volume":"146","author":"Wang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026102208022643400_cit16","doi-asserted-by":"publisher","first-page":"690","DOI":"10.1038\/s41467-024-55719-4","article-title":"Visualizing Stepwise Evolution of\nCarbon Hybridization from sp3 to sp2 and to\nsp","volume":"16","author":"Xiong","year":"2025","journal-title":"Nat. Commun."},{"key":"2026102208022643400_cit17","doi-asserted-by":"publisher","first-page":"7012","DOI":"10.1021\/jacs.7b02430","article-title":"Intermolecular On-Surface\n\u03c3-Bond Metathesis","volume":"139","author":"Gao","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"2026102208022643400_cit18","doi-asserted-by":"publisher","first-page":"8791","DOI":"10.1021\/acsnano.8b05116","article-title":"Diacetylene Linked\nAnthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl\non Cu(111)","volume":"12","author":"Kawai","year":"2018","journal-title":"ACS Nano"},{"key":"2026102208022643400_cit19","doi-asserted-by":"publisher","first-page":"8789","DOI":"10.1021\/jacs.2c02762","article-title":"Desilylative\nCoupling Involving C(sp2)\u2013Si Bond Cleavage on Metal\nSurfaces","volume":"144","author":"Ma","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026102208022643400_cit20","doi-asserted-by":"publisher","first-page":"4754","DOI":"10.1007\/s12274-021-3419-2","article-title":"On-surface\nactivation of benzylic CH bonds for the synthesis of pentagon-fused\ngraphene nanoribbons","volume":"14","author":"Xu","year":"2021","journal-title":"Nano Res."},{"key":"2026102208022643400_cit21","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202318185","article-title":"On-Surface Synthesis\nof Non-Benzenoid Nanographenes Embedding Azulene and Stone-Wales Topologies","volume":"63","author":"Biswas","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026102208022643400_cit22","doi-asserted-by":"publisher","first-page":"1609","DOI":"10.1002\/anie.199516091","article-title":"Diodelike Current\u2013Voltage\nCurves for a Single Molecule\u2013Tunneling Spectroscopy with Submolecular\nResolution of an Alkylated, peri-Condensed Hexabenzocoronene","volume":"34","author":"Stabel","year":"1995","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"2026102208022643400_cit23","doi-asserted-by":"publisher","first-page":"4817","DOI":"10.1021\/ol702158a","article-title":"Synthesis\nof 2,5,8,11,14,17-Hexafluoro-hexa-peri-\nhexabenzocoronene for n-Type Organic Field-Effect Transistors","volume":"9","author":"Kikuzawa","year":"2007","journal-title":"Org. Lett."},{"key":"2026102208022643400_cit24","doi-asserted-by":"publisher","first-page":"516","DOI":"10.1038\/s41557-023-01149-6","article-title":"Rupturing aromaticity by periphery overcrowding","volume":"15","author":"Saha","year":"2023","journal-title":"Nat. Chem."},{"key":"2026102208022643400_cit25","doi-asserted-by":"publisher","first-page":"566","DOI":"10.1021\/nn203952e","article-title":"Supramolecular Self-Assembly\nof \u03c0-Conjugated Hydrocarbons via 2D Cooperative\nCH\/\u03c0 Interaction","volume":"6","author":"Li","year":"2012","journal-title":"ACS Nano"},{"key":"2026102208022643400_cit26","doi-asserted-by":"publisher","first-page":"6111","DOI":"10.1021\/jacs.6b02412","article-title":"Aggregation\nof C70-Fragment Buckybowls on Surfaces: \u03c0\u2013H\nand \u03c0\u2013\u03c0 Bonding in Bowl Up-Side-Down Ensembles","volume":"138","author":"Sto\u0308ckl","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026102208022643400_cit27","doi-asserted-by":"publisher","first-page":"7628","DOI":"10.1021\/acs.jpclett.4c01364","article-title":"Procrystalline Self-Assembly of Desymmetrized\nPentaphenylcyclopentadiene","volume":"15","author":"Li","year":"2024","journal-title":"J. Phys. Chem. Lett."},{"key":"2026102208022643400_cit28","doi-asserted-by":"publisher","first-page":"1769","DOI":"10.1002\/cphc.202100049","article-title":"Structure Formation\nand Coupling Reactions of Hexaphenylbenzene\nand Its Brominated Analog","volume":"22","author":"Teeter","year":"2021","journal-title":"ChemPhysChem"},{"key":"2026102208022643400_cit29","doi-asserted-by":"publisher","first-page":"9228","DOI":"10.1021\/acsnano.5b03895","article-title":"On-Surface\nSynthesis of BN-Substituted Heteroaromatic Networks","volume":"9","author":"Sa\u0301nchez-Sa\u0301nchez","year":"2015","journal-title":"ACS Nano"},{"issue":"5","key":"2026102208022643400_cit30","doi-asserted-by":"publisher","first-page":"3777","DOI":"10.1021\/acscatal.4c06226","article-title":"Direct Synthesis of\nHexa-peri-hexabenzocoronene on Au(111) Surfaces: Insights into Intramolecular\nDehydrocyclization and Molecular Modification Strategies","volume":"15","author":"Wang","year":"2025","journal-title":"ACS Catal."},{"key":"2026102208022643400_cit31","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202411722","article-title":"Synthesis of Hexabenzocoronene-Cored\nGraphdiyne Nanosheets through Dehydrogenative Coupling on Au(111)\nSurface","volume":"63","author":"Wang","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026102208022643400_cit32","doi-asserted-by":"publisher","first-page":"1110","DOI":"10.1126\/science.1176210","article-title":"The chemical structure of a molecule\nresolved by atomic force microscopy","volume":"325","author":"Gross","year":"2009","journal-title":"Science"},{"key":"2026102208022643400_cit33","doi-asserted-by":"publisher","DOI":"10.1088\/1367-2630\/10\/5\/053012","article-title":"A Novel\nMethod Achieving Ultra-High Geometrical Resolution in Scanning Tunneling\nMicroscopy","volume":"10","author":"Temirov","year":"2008","journal-title":"New J. Phys."},{"key":"2026102208022643400_cit34","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.81.035423","article-title":"Repulsion between Molecules on a\nMetal: Monolayers and Submonolayers of Hexa-Peri-Hexabenzocoronene\non Au(111)","volume":"81","author":"Wagner","year":"2010","journal-title":"Phys. Rev. B"},{"key":"2026102208022643400_cit35","doi-asserted-by":"publisher","first-page":"9098","DOI":"10.1021\/nn403672m","article-title":"Obtaining Detailed Structural Information\nabout Supramolecular Systems on Surfaces by Combining High-Resolution\nForce Microscopy with ab Initio Calculations","volume":"7","author":"Kawai","year":"2013","journal-title":"ACS Nano"},{"key":"2026102208022643400_cit36","doi-asserted-by":"publisher","first-page":"112","DOI":"10.1002\/adma.200601825","article-title":"The Effect\nof Fluorination on Pentacene\/Gold Interface Energetics and Charge\nReorganization Energy","volume":"19","author":"Koch","year":"2007","journal-title":"Adv. Mater."},{"key":"2026102208022643400_cit37","doi-asserted-by":"publisher","first-page":"2598","DOI":"10.1039\/D1NA00040C","article-title":"Pentacene\/perfluoropentacene Bilayers\non Au(111) and\nCu(111): Impact of Organic\u2013Metal Coupling Strength on Molecular\nStructure Formation","volume":"3","author":"Wang","year":"2021","journal-title":"Nanoscale Adv."},{"key":"2026102208022643400_cit38","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.107.086101","article-title":"High-Resolution\nMolecular Orbital\nImaging Using a p-Wave STM Tip","volume":"107","author":"Gross","year":"2011","journal-title":"Phys. Rev. Lett."},{"key":"2026102208022643400_cit39","doi-asserted-by":"publisher","first-page":"6127","DOI":"10.1021\/nl502113z","article-title":"Image Distortions of\nPartly Fluorinated Hydrocarbons in Atomic Force Microscopy with Carbon\nMonoxide Terminated Tip","volume":"14","author":"Moll","year":"2014","journal-title":"Nano Lett."}],"container-title":["The Journal of Physical\nChemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jpclett.6c01675","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article-pdf\/17\/42\/12171\/67409946\/acs.jpclett.6c01675.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article-pdf\/17\/42\/12171\/67409946\/acs.jpclett.6c01675.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T12:10:07Z","timestamp":1792671007000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article\/17\/42\/12171\/5329134\/On-Surface-Synthesis-of-Hexabenzocoronenes-via-a"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,25]]},"references-count":39,"journal-issue":{"issue":"42","published-online":{"date-parts":[[2026,8,25]]},"published-print":{"date-parts":[[2026,10,22]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jpclett.6c01675","relation":{},"ISSN":["1948-7185"],"issn-type":[{"value":"1948-7185","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,25]]}}}