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In molecular semiconductors, self-assembly pathways and the resulting supramolecular superstructures play a decisive role in dictating the molecular packing, which in turn governs charge-transport efficiency. Therefore, weak noncovalent interactions must be carefully engineered to fine-tune molecular stacking motifs. Herein, we investigate the role of halogen-bonded intermolecular interactions in directing naphthalenediimide (NDI) stacks toward temperature-induced realignment, leading to robust brickwork-type molecular assemblies in both thin films and solids. This structural reorganization significantly influences their optical properties and electron transport characteristics. In core-unsubstituted NDI derivatives, assembly is typically governed by hydrogen-bond-driven in-plane interactions, resulting in slipped one-dimensional columnar stacks. In contrast, brominated NDI cores promote halogen-bond-mediated organization, yielding efficient brickwork stacking motifs, either in their pristine state or after thermal realignment, depending on the end-group substitution. In summary, hydrogen-bond-dominated assembly pathways tend to produce poorly stacked domains with limited charge-transport efficiency, whereas halogen-bond-driven pathways generate well-ordered brickwork assemblies that facilitate superior electron mobility. To substantiate these findings, we performed comprehensive optical measurements, grazing incidence wide angle X-ray scattering (GIWAXS) analysis, and electrical characterization of organic field-effect transistors (OFETs).<\/jats:p>","DOI":"10.1021\/acs.jpclett.6c01870","type":"journal-article","created":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T22:02:02Z","timestamp":1788559322000},"page":"10584-10593","source":"Crossref","is-referenced-by-count":0,"title":["Halogen-Bonding-Steered\nThermal Reassembly into Brickwork\nPacking Motifs Enhances Electron Transport in Naphthalenediimides"],"prefix":"10.1021","volume":"17","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-3741-0126","authenticated-orcid":true,"given":"Shant","family":"Chhetri","sequence":"first","affiliation":[{"name":"Indian Institute of Science Education and Research, Kolkata , , , Nadia , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-8186-8788","authenticated-orcid":true,"given":"Jesslyn","family":"John P","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research, Kolkata , , , Nadia , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pampi","family":"Saha","sequence":"additional","affiliation":[{"name":"Deutsches Elektronen-Synchrotron DESY , Notkestr. 85 , ,","place":["Hamburg, Germany, 22607"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adarsh","family":"Babukkuttan Nair","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Maruthamala P.O. , , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8952-8087","authenticated-orcid":true,"given":"Ratheesh K","family":"Vijayaraghavan","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research, Kolkata , , , Nadia , ,","place":["Mohanpur, West Bengal, India, 741246"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,4]]},"reference":[{"key":"2026091709085701700_cit1","doi-asserted-by":"publisher","first-page":"926","DOI":"10.1021\/cr050140x","article-title":"Charge Transport in Organic Semiconductors","volume":"107","author":"Coropceanu","year":"2007","journal-title":"Chem. 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