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Here, we demonstrate that directional noncovalent interactions can regulate hierarchical reaction pathways through molecular recognition, enabling the formation of orientationally ordered surface nanostructures. Using 4,7-dibromobenzo[c][1,2,5]thiadiazole (2Br-BTD) on Ag(111) as a model system, we combine scanning tunneling microscopy, bond-resolved noncontact atomic force microscopy, and density functional theory calculations to reveal a sequential reaction pathway involving self-assembled monomers, cis-organometallic dimers, trans-covalent dimers, and ultimately alternating organometallic chains. Cooperative S\u00b7\u00b7\u00b7N chalcogen bonding is found to critically and selectively stabilize the cis-organometallic nodes throughout this process, driving both initial dimer formation and subsequent ordered chain synthesis. Chemically matched control experiments with 4,7-dibromobenzo[c][1,2,5]selenadiazole (2Br-BSe) and 5,8-dibromoquinoxaline (2Br-Qx) further demonstrate that analogous orientational selectivity can be achieved through strengthened Se\u00b7\u00b7\u00b7N chalcogen bonding and C\u2013H\u00b7\u00b7\u00b7N hydrogen bonding, respectively. By contrast, the heteroatom-free analogue 1,4-dibromonaphthalene (2Br-Nap), which lacks such directional interaction motifs, exhibits no such selectivity. These results establish directional noncovalent interactions as an effective means of steering surface reaction pathways, offering new insights into the rational design of orientationally ordered low-dimensional nanostructures.<\/jats:p>","DOI":"10.1021\/jacs.5c21999","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T16:20:37Z","timestamp":1788452437000},"page":"38597-38607","source":"Crossref","is-referenced-by-count":0,"title":["Construction of Orientationally\nOrdered Organometallic\nChains by Directional Noncovalent Interactions"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0009-0005-5218-7625","authenticated-orcid":true,"given":"Jie","family":"Li","sequence":"first","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]},{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhen","family":"Xu","sequence":"additional","affiliation":[{"name":"Nanjing Tech University , , ,","place":["Nanjing, China, 211816"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongxiang","family":"Xu","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-1096-2039","authenticated-orcid":true,"given":"Haoyang","family":"Pan","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tianhao","family":"Wu","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Minghui","family":"Yu","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Zhao","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6206-0613","authenticated-orcid":true,"given":"Xin","family":"Li","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0204-9601","authenticated-orcid":true,"given":"Shang-Da","family":"Jiang","sequence":"additional","affiliation":[{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5016-0251","authenticated-orcid":true,"given":"Kai","family":"Wu","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0754-074X","authenticated-orcid":true,"given":"Lian-Mao","family":"Peng","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5042-4405","authenticated-orcid":true,"given":"Shimin","family":"Hou","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 100871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7141-4660","authenticated-orcid":true,"given":"Peng","family":"He","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Taiyuan, China, 030001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0039-6346","authenticated-orcid":true,"given":"Song","family":"Gao","sequence":"additional","affiliation":[{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8171-3189","authenticated-orcid":true,"given":"Yongfeng","family":"Wang","sequence":"additional","affiliation":[{"name":"Peking University , , ,","place":["Beijing, China, 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