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While switching between bistable molecular conformers is common in nature, creating systems with multiple, addressable states remains synthetically challenging. Here, we demonstrate a bottom-up strategy in which intermolecular interactions give rise to multilevel functionality within a simple two-molecule assembly. Using low-temperature scanning tunneling microscopy, we show that a pyrrolidine dimer on Cu(100) exhibits six distinct adsorption conformations, exceeding the four expected from two independent bistable units. This unusual complexity arises from the interplay between intermolecular van der Waals attraction and steric repulsion, which reshapes the potential energy landscape and changes a single high-energy transition into a sequential two-step pathway. Each step is driven by low-energy inelastic electron excitations, achieving a switching efficiency an order of magnitude higher than that of the monomer. By tuning the bias voltage and tip\u2013molecule distance, we achieve deterministic control over multiple stable states, establishing a general design principle for on-demand engineering of collective molecular behavior and energy-efficient multilevel molecular devices.<\/jats:p>","DOI":"10.1021\/jacs.5c23182","type":"journal-article","created":{"date-parts":[[2026,4,30]],"date-time":"2026-04-30T20:07:12Z","timestamp":1777579632000},"page":"23628-23635","source":"Crossref","is-referenced-by-count":2,"title":["Engineering Structural\nTransitions in a Multilevel\nMolecular Switch via Intermolecular Coupling"],"prefix":"10.1021","volume":"148","author":[{"given":"Yueqing","family":"Shi","sequence":"first","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zihao","family":"Wang","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weike","family":"Quan","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-3041-2771","authenticated-orcid":true,"given":"Liya","family":"Bi","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8434-6743","authenticated-orcid":true,"given":"Kangkai","family":"Liang","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hao","family":"Zhou","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-7275-9668","authenticated-orcid":true,"given":"Zhiyuan","family":"Yin","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0098-0670","authenticated-orcid":true,"given":"Wan-Lu","family":"Li","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]},{"name":"University of California , , , La Jolla, ,","place":["San Diego, California, United States, 92093-0448"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4627-626X","authenticated-orcid":true,"given":"Shaowei","family":"Li","sequence":"additional","affiliation":[{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0358"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0418"]},{"name":"University of California, San Diego , , , ,","place":["La Jolla, California, United States, 92093-0112"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,4,30]]},"reference":[{"issue":"29","key":"2026072621074316100_cit1","doi-asserted-by":"publisher","DOI":"10.1002\/advs.202400877","article-title":"Toward Practical Single-Molecule\/Atom\nSwitches","volume":"11","author":"Xu","year":"2024","journal-title":"Adv. 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Nanotechnol."},{"issue":"5","key":"2026072621074316100_cit5","doi-asserted-by":"publisher","first-page":"834","DOI":"10.1002\/tcr.201402007","article-title":"Development of an electrically driven molecular motor","volume":"14","author":"Murphy","year":"2014","journal-title":"Chem. Rec."},{"issue":"47","key":"2026072621074316100_cit6","doi-asserted-by":"publisher","first-page":"31931","DOI":"10.1039\/C5CP05294G","article-title":"Ullmann\ncoupling mediated assembly of an electrically driven altitudinal molecular\nrotor","volume":"17","author":"Murphy","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"1","key":"2026072621074316100_cit7","doi-asserted-by":"publisher","first-page":"46","DOI":"10.1038\/nnano.2012.218","article-title":"Controlled\nclockwise and anticlockwise rotational switching\nof a molecular motor","volume":"8","author":"Perera","year":"2013","journal-title":"Nat. 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Matter"},{"issue":"2","key":"2026072621074316100_cit48","doi-asserted-by":"publisher","first-page":"109","DOI":"10.1002\/sia.1663","article-title":"Manipulation of large molecules by\nlow temperature STM","volume":"36","author":"Moresco","year":"2004","journal-title":"Surf. Interface Anal."},{"issue":"6266","key":"2026072621074316100_cit49","doi-asserted-by":"publisher","first-page":"524","DOI":"10.1038\/344524a0","article-title":"Positioning\nsingle atoms with a scanning tunnelling\nmicroscope","volume":"344","author":"Eigler","year":"1990","journal-title":"Nature"},{"key":"2026072621074316100_cit50","doi-asserted-by":"publisher","first-page":"1079","DOI":"10.1016\/S0039-6028(00)00072-8","article-title":"Controlled\nlateral manipulation of single diiodobenzene molecules on the Cu(111)\nsurface with the tip of a scanning tunnelling microscope","volume":"454\u2013456","author":"Hla","year":"2000","journal-title":"Surf. 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