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Several atomically precise edge structures have been prepared by bottom\u2010up synthesis; however, no systematic elucidation of these edge topologies at the molecular level has been reported. Herein, we describe rationally designed modular syntheses of isomeric dibenzoixenes with diverse molecular peripheries, including cove, zigzag, bay, fjord, and gulf structured. The single\u2010crystal structures of dibenzo[\n                    <jats:italic>a<\/jats:italic>\n                    ,\n                    <jats:italic>p<\/jats:italic>\n                    ]ixene and dibenzo[\n                    <jats:italic>j<\/jats:italic>\n                    ,\n                    <jats:italic>y<\/jats:italic>\n                    ]ixene reveal enantiomeric pairs with helically twisted cove edges and packing structures. The molecular edge structures are identified from the C\u2212H bonds of the dibenzoixenes using Fourier transform infrared spectroscopy with different vibrational modes, which were further explained using density functional theory calculations. Electron spin resonance spectroscopy indicates that the zigzag\u2010edged molecular periphery significantly affects the magnetic properties of the material. Furthermore, the electrochemical characteristics, examined using dibenzoixenes as anode materials in Li\u2010ion batteries, reveal that the dibenzo[\n                    <jats:italic>a<\/jats:italic>\n                    ,\n                    <jats:italic>p<\/jats:italic>\n                    ]ixene exhibits promising Li intercalation behaviors with a specific capacity of ~120\u2005mAh\u2009g\n                    <jats:sup>\u22121<\/jats:sup>\n                    . The findings of this study could facilitate the synthesis of larger \n\u2010extended systems with engineered molecular peripheries and potential application in organic electronics.\n                  <\/jats:p>","DOI":"10.1002\/chem.202404189","type":"journal-article","created":{"date-parts":[[2024,12,23]],"date-time":"2024-12-23T11:29:11Z","timestamp":1734953351000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Achieving Precise Control Over the Molecular Periphery of Dibenzoixenes Through Modular Synthesis"],"prefix":"10.1002","volume":"31","author":[{"given":"Seongrok","family":"Shin","sequence":"first","affiliation":[{"name":"Department of Chemistry Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hwon","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jee Ho","family":"Ha","sequence":"additional","affiliation":[{"name":"Department of Energy Engineering Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kyung Yeon","family":"Eun","sequence":"additional","affiliation":[{"name":"Department of Energy Engineering Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiyeon","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of 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Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seok Ju","family":"Kang","sequence":"additional","affiliation":[{"name":"Department of Energy Engineering Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Seung Kyu","family":"Min","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher W.","family":"Bielawski","sequence":"additional","affiliation":[{"name":"Department of Chemistry Ulsan National Institute of Science and Technology (UNIST)  50 UNIST-gil Ulsan 44919 Republic of Korea"},{"name":"Center for Multidimensional Carbon Materials (CMCM) Institute for Basic Science  50 UNIST-gil Ulsan 44919 Republic of 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