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In ambipolar semiconductors, where both holes and electrons participate in conduction, distinct molecular orbitals prompt a critical inquiry: can orbital variations result in coexisting yet distinct anisotropic transport properties within a single component? We confirm this possibility by demonstrating that the air\u2010stable nickel dithiolene,\n                    <jats:bold>Ni(4OPr)<\/jats:bold>\n                    , exhibits such behavior. Despite its herringbone stacking implying a two\u2010dimensional electronic structure,\n                    <jats:bold>Ni(4OPr)<\/jats:bold>\n                    uniquely exhibits distinct intermolecular interactions for hole (HOMO\u2010to\u2010HOMO; HOMO = highest occupied molecular orbital) and electron (LUMO\u2010to\u2010LUMO; LUMO = lowest unoccupied molecular orbital) transport. Crucially, this leads to highly anisotropic hole transport pathways, while electron pathways are remarkably isotropic, demonstrating a stark contrast in their transport anisotropies. Leveraging the high crystallinity, grazing\u2010incidence wide\u2010angle X\u2010ray scattering (GIWAXS) determined in\u2010plane molecular orientation. This enabled experimental verification of distinct anisotropic hole and electron transport, directly governed by orbital\u2010specific intermolecular interactions, in an ambipolar molecular semiconductor. Our findings, demonstrating coexisting yet distinct anisotropic transport properties for both carriers within a single component, significantly advance the understanding of ambipolar molecular semiconductors and broaden their scope for future device applications.\n                  <\/jats:p>","DOI":"10.1002\/anie.202512609","type":"journal-article","created":{"date-parts":[[2025,9,4]],"date-time":"2025-09-04T06:45:35Z","timestamp":1756968335000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Distinct Hole and Electron Transport Anisotropy in Ambipolar Nickel Dithiolene\u2010Based Semiconductor"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4123-9344","authenticated-orcid":false,"given":"Masatoshi","family":"Ito","sequence":"first","affiliation":[{"name":"The Institute for Solid State Physics The University of Tokyo 5\u20101\u20105 Kashiwanoha Kashiwa Chiba 277\u20108581 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Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4511-4039","authenticated-orcid":false,"given":"Mafumi","family":"Hishida","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of\u00a0Science Tokyo University of Science 1\u20133 Kagurazaka Shinjuku Tokyo 162\u20108601 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hatsumi","family":"Mori","sequence":"additional","affiliation":[{"name":"The Institute for Solid State Physics The University of Tokyo 5\u20101\u20105 Kashiwanoha Kashiwa Chiba 277\u20108581 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