{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T15:54:52Z","timestamp":1791474892091,"version":"4.3.4"},"reference-count":36,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T00:00:00Z","timestamp":1790208000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T00:00:00Z","timestamp":1790208000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T00:00:00Z","timestamp":1790208000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21972104"],"award-info":[{"award-number":["21972104"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22372119"],"award-info":[{"award-number":["22372119"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Haihe Laboratory of Sustainable Chemical Transformation","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Controlling stereoselectivity in competing on-surface reactions remains a fundamental challenge for the bottom-up synthesis of covalent nanostructures. Herein, we employ scanning tunneling microscopy (STM), scanning tunneling spectroscopy (STS), and density functional theory (DFT) calculations to investigate on-surface self-assembly and reaction of 6,6\u201d-dibromo-2,2\u2019:6\u2019,2\u201d-terpyridine (DT) on Au(111) and Cu(111). After thermal annealing, DT molecules yield trans-chain structures and the nitrogen-doped porous nanocarbon networks (n-NPCNs). The resulting 3-NPCNs exhibit an electronic bandgap of \u223c1.35 eV. Importantly, we successfully demonstrate that the alkali-metal salts act as effective external additives for steering the stereoselectivity of DT reaction. Co-deposition of NaCl or KCl significantly enhances cis-ring formation. A maximum cis-ring selectivity of 91.9 \u00b1 3.6% is achieved with NaCl on Cu(111), while KCl also substantially promotes cis-ring formation. DFT calculations suggest that the enhanced cis-ring selectivity is associated with electrostatic stabilization between alkali metal ions and the N-rich cavity of the cis-ring structure. These findings provide mechanistic insight into the stereoselective control of on-surface reactions and offer an effective approach for controlling the construction of low-dimensional covalent nanoarchitectures.<\/jats:p>","DOI":"10.1021\/acs.jpclett.6c02350","type":"journal-article","created":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T23:14:59Z","timestamp":1790291699000},"page":"11539-11544","source":"Crossref","is-referenced-by-count":0,"title":["Cis\/Trans Stereoselectivity\nof 6,6\u201d-Dibromo-2,2\u2019:6\u2019,2\u201d-Terpyridine\nSteered by Alkali Metal Salts on Metal Surfaces"],"prefix":"10.1021","volume":"17","author":[{"given":"Yexin","family":"Shi","sequence":"first","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongchao","family":"Wang","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Shandong University of Technology , , ,","place":["Zibo, Shandong, P. R. China, 255000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zikun","family":"Yang","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peichao","family":"Wang","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peisong","family":"Han","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hafiz Mahmood","family":"Ul Hasan","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3253-6964","authenticated-orcid":true,"given":"Zhixin","family":"Hu","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6831-9112","authenticated-orcid":true,"given":"Hong-Ying","family":"Gao","sequence":"additional","affiliation":[{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations , ,","place":["Tianjin, P. R. China, 300192"]},{"name":"Tianjin University , , ,","place":["Tianjin, P. R. China, 300350"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,24]]},"reference":[{"key":"2026100811165732700_cit1","doi-asserted-by":"publisher","first-page":"4717","DOI":"10.1021\/acs.chemrev.8b00601","article-title":"Controlling a Chemical Coupling Reaction on a Surface:\nTools and Strategies for On-Surface Synthesis","volume":"119","author":"Clair","year":"2019","journal-title":"Chem. Rev."},{"key":"2026100811165732700_cit2","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1038\/s41557-019-0392-9","article-title":"Covalent On-Surface Polymerization","volume":"12","author":"Grill","year":"2020","journal-title":"Nat. Chem."},{"key":"2026100811165732700_cit3","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1016\/j.nantod.2017.02.007","article-title":"Frontiers\nof On-Surface Synthesis:\nfrom Principles to Applications","volume":"13","author":"Shen","year":"2017","journal-title":"Nano Today"},{"key":"2026100811165732700_cit4","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/j.surfrep.2019.05.001","article-title":"Confined On-Surface\nOrganic Synthesis: Strategies and Mechanisms","volume":"74","author":"Wang","year":"2019","journal-title":"Surf. Sci. Rep."},{"key":"2026100811165732700_cit5","doi-asserted-by":"publisher","first-page":"61","DOI":"10.1038\/nchem.891","article-title":"Surface-Assisted Cyclodehydrogenation\nProvides a Synthetic Route Towards Easily Processable and Chemically\nTailored Nanographenes","volume":"3","author":"Treier","year":"2011","journal-title":"Nat. Chem."},{"key":"2026100811165732700_cit6","doi-asserted-by":"publisher","first-page":"4668","DOI":"10.1002\/anie.201300610","article-title":"Surface-Assisted\nOrganic Synthesis of Hyperbenzene Nanotroughs","volume":"52","author":"Fan","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026100811165732700_cit7","doi-asserted-by":"publisher","first-page":"4824","DOI":"10.1021\/jacs.8b11473","article-title":"The Role of Kinetics versus Thermodynamics in Surface-Assisted\nUllmann Coupling on Gold and Silver Surfaces","volume":"141","author":"Fritton","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit8","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. Nanotechnol."},{"key":"2026100811165732700_cit9","doi-asserted-by":"publisher","first-page":"470","DOI":"10.1038\/nature09211","article-title":"Atomically Precise Bottom-Up Fabrication of Graphene Nanoribbons","volume":"466","author":"Cai","year":"2010","journal-title":"Nature"},{"key":"2026100811165732700_cit10","doi-asserted-by":"publisher","first-page":"12955","DOI":"10.1021\/jacs.1c05586","article-title":"Ladder Phenylenes Synthesized on Au(111) Surface via\nSelective [2 + 2] Cycloaddition","volume":"143","author":"Li","year":"2021","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026100811165732700_cit11","doi-asserted-by":"publisher","first-page":"4024","DOI":"10.1002\/anie.201208597","article-title":"Glaser Coupling\nat Metal Surfaces","volume":"52","author":"Gao","year":"2013","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026100811165732700_cit12","doi-asserted-by":"publisher","first-page":"1286","DOI":"10.1038\/ncomms2291","article-title":"Homo-Coupling\nof Terminal Alkynes on a Noble Metal Surface","volume":"3","author":"Zhang","year":"2012","journal-title":"Nat. Commun."},{"key":"2026100811165732700_cit13","doi-asserted-by":"publisher","first-page":"13421","DOI":"10.1021\/jacs.8b08477","article-title":"Kinetic Strategies\nfor the Formation of Graphyne Nanowires via Sonogashira Coupling on\nAg(111)","volume":"140","author":"Wang","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit14","doi-asserted-by":"publisher","first-page":"8081","DOI":"10.1021\/ja1011542","article-title":"Sonogashira Coupling\non an Extended\nGold Surface in Vacuo: Reaction of Phenylacetylene with Iodobenzene\non Au(111)","volume":"132","author":"Kanuru","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit15","doi-asserted-by":"publisher","first-page":"19598","DOI":"10.1002\/anie.202102882","article-title":"Head-to-Tail Oligomerization\nby Silylene-Tethered Sonogashira Coupling\non Ag(111)","volume":"60","author":"Sun","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026100811165732700_cit16","doi-asserted-by":"publisher","first-page":"220","DOI":"10.1038\/nchem.2438","article-title":"Reversible Bergman\nCyclization by Atomic Manipulation","volume":"8","author":"Schuler","year":"2016","journal-title":"Nat. Chem."},{"key":"2026100811165732700_cit17","doi-asserted-by":"publisher","first-page":"6272","DOI":"10.1021\/jp411889e","article-title":"Photochemical Glaser\nCoupling at Metal Surfaces","volume":"118","author":"Gao","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"2026100811165732700_cit18","doi-asserted-by":"publisher","first-page":"e6649441","DOI":"10.1002\/ange.6649441","article-title":"Highly Selective On-Surface\nSynthesis of sp2\/sp-Hybridized Heterochiral Triangular\nNanorings","volume":"138","author":"Zhang","year":"2026","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026100811165732700_cit19","doi-asserted-by":"publisher","first-page":"12085","DOI":"10.1021\/acscatal.5c04254","article-title":"Selective C-H Activation Facilitated\nby the Cooperative Effect of Extrinsic O2 and Na on Ag(111)","volume":"15","author":"Zhang","year":"2025","journal-title":"ACS Catal."},{"key":"2026100811165732700_cit20","doi-asserted-by":"publisher","first-page":"5837","DOI":"10.1021\/jacs.5b11594","article-title":"Driving Forces\nfor Covalent Assembly\nof Porphyrins by Selective C-H Bond Activation and Intermolecular\nCoupling on a Copper Surface","volume":"138","author":"Floris","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit21","doi-asserted-by":"publisher","first-page":"4617","DOI":"10.1021\/acsnano.0c08920","article-title":"Topology Selectivity\nin On-Surface Dehydrogenative\nCoupling Reaction: Dendritic Structure versus Porous Graphene Nanoribbon","volume":"15","author":"Huang","year":"2021","journal-title":"ACS Nano"},{"key":"2026100811165732700_cit22","doi-asserted-by":"publisher","first-page":"10282","DOI":"10.1021\/jacs.2c01026","article-title":"Steering the Reaction Pathways of\nTerminal Alkynes by Introducing Oxygen Species: From C-C Coupling\nto C-H Activation","volume":"144","author":"Zhang","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit23","doi-asserted-by":"publisher","first-page":"12694","DOI":"10.1039\/C6CC05849C","article-title":"Surface-Assisted\nDiastereoselective Ullmann Coupling of Bishelicenes","volume":"52","author":"Wa\u0308ckerlin","year":"2016","journal-title":"Chem. Commun."},{"key":"2026100811165732700_cit24","doi-asserted-by":"publisher","first-page":"8356","DOI":"10.1002\/anie.201900636","article-title":"Surface-Dependent Chemoselectivity in C-C Coupling Reactions","volume":"58","author":"Chen","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026100811165732700_cit25","doi-asserted-by":"publisher","first-page":"4545","DOI":"10.1021\/jacs.2c11799","article-title":"Pyridinic Nitrogen Modification for Selective Acetylenic Homocoupling\non Au(111)","volume":"145","author":"Li","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"2026100811165732700_cit26","doi-asserted-by":"publisher","first-page":"709","DOI":"10.1021\/nn405370s","article-title":"Surface-Assisted\nFormation, Assembly,\nand Dynamics of Planar Organometallic Macrocycles and Zigzag Shaped\nPolymer Chains with C-Cu-C Bonds","volume":"8","author":"Fan","year":"2014","journal-title":"ACS Nano"},{"key":"2026100811165732700_cit27","doi-asserted-by":"publisher","first-page":"843","DOI":"10.1002\/cphc.201901210","article-title":"Directing\nOn-Surface Reaction Pathways via Metal-Organic Cu-N Coordination","volume":"21","author":"Liang","year":"2020","journal-title":"ChemPhysChem"},{"key":"2026100811165732700_cit28","doi-asserted-by":"publisher","first-page":"112","DOI":"10.3390\/chemistry4010009","article-title":"On-Surface Synthesis of Polypyridine:\nStrain Enforces Extended Linear Chains","volume":"4","author":"Patera","year":"2022","journal-title":"Chemistry"},{"key":"2026100811165732700_cit29","doi-asserted-by":"publisher","first-page":"40","DOI":"10.1038\/s42004-024-01123-4","article-title":"Stepwise On-Surface\nSynthesis of Nitrogen-Doped Porous Carbon Nanoribbons","volume":"7","author":"Xu","year":"2024","journal-title":"Commun. Chem."},{"key":"2026100811165732700_cit30","doi-asserted-by":"publisher","first-page":"11862","DOI":"10.1021\/acs.jpclett.4c03040","article-title":"Controlling\nthe Selectivity of Reaction\nProducts by Transmetalation on a Ag(111) Substrate","volume":"15","author":"Xu","year":"2024","journal-title":"J. Phys. Chem. Lett."},{"key":"2026100811165732700_cit31","doi-asserted-by":"publisher","first-page":"11169","DOI":"10.1103\/PhysRevB.54.11169","article-title":"Efficient Iterative Schemes for ab\nInitio Total-Energy\nCalculations Using a Plane-Wave Basis Set","volume":"54","author":"Kresse","year":"1996","journal-title":"Phys.\nRev. B"},{"key":"2026100811165732700_cit32","doi-asserted-by":"publisher","first-page":"17953","DOI":"10.1103\/PhysRevB.50.17953","article-title":"Projector\nAugmented-Wave Method","volume":"50","author":"Blo\u0308chl","year":"1994","journal-title":"Phys. Rev. B"},{"key":"2026100811165732700_cit33","doi-asserted-by":"publisher","first-page":"1758","DOI":"10.1103\/PhysRevB.59.1758","article-title":"From Ultrasoft Pseudopotentials\nto the Projector Augmented-Wave\nMethod","volume":"59","author":"Kresse","year":"1999","journal-title":"Phys. Rev. B"},{"key":"2026100811165732700_cit34","doi-asserted-by":"publisher","first-page":"3865","DOI":"10.1103\/PhysRevLett.77.3865","article-title":"Generalized\nGradient Approximation\nMade Simple","volume":"77","author":"Perdew","year":"1996","journal-title":"Phys. Rev. Lett."},{"key":"2026100811165732700_cit35","doi-asserted-by":"publisher","first-page":"154104","DOI":"10.1063\/1.3382344","article-title":"A Consistent and Accurate\nab Initio Parametrization of Density Functional Dispersion Correction\n(DFT-D) for the 94 elements H-Pu","volume":"132","author":"Grimme","year":"2010","journal-title":"J. Chem. Phys."},{"key":"2026100811165732700_cit36","doi-asserted-by":"publisher","first-page":"805","DOI":"10.1103\/PhysRevB.31.805","article-title":"Theory of the Scanning\nTunneling Microscope","volume":"31","author":"Tersoff","year":"1985","journal-title":"Phys. Rev. B"}],"container-title":["The Journal of Physical\nChemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jpclett.6c02350","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article-pdf\/17\/40\/11539\/68645133\/acs.jpclett.6c02350.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article-pdf\/17\/40\/11539\/68645133\/acs.jpclett.6c02350.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T15:19:42Z","timestamp":1791472782000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jpclcd\/article\/17\/40\/11539\/5438037\/Cis-Trans-Stereoselectivity-of-6-6-Dibromo-2-2-6-2"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,24]]},"references-count":36,"journal-issue":{"issue":"40","published-online":{"date-parts":[[2026,9,24]]},"published-print":{"date-parts":[[2026,10,8]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jpclett.6c02350","relation":{},"ISSN":["1948-7185"],"issn-type":[{"value":"1948-7185","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,24]]}}}