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Especially the separation of cyclic aliphatic hydrocarbons from their aromatic counterparts remains a significant challenge due to azeotrope formation and similar physical properties, often requiring energy\u2010intensive processes. Herein, we introduce a novel class of electron\u2010deficient macrocycles with a unique rectangular structure to optimise interactions within the pore, enabling the highly selective molecular sieving of aromatic compounds from mixtures. Utilising dynamic covalent imine chemistry, the squareimine\n                    <jats:bold>\n                      NDI\n                      <jats:sup>2<\/jats:sup>\n                      F4\n                      <jats:sup>2<\/jats:sup>\n                    <\/jats:bold>\n                    \u2010based crystalline functional material is directly obtained from the reaction mixture in a single self\u2010assembly step in high yields of 83\u2009%, alongside the larger\n                    <jats:bold>\n                      NDI\n                      <jats:sup>2<\/jats:sup>\n                      F8\n                      <jats:sup>2<\/jats:sup>\n                    <\/jats:bold>\n                    congener, which can be obtained in 69\u2009% yield. In vapour sorption and diffusion experiments,\n                    <jats:bold>\n                      NDI\n                      <jats:sup>2<\/jats:sup>\n                      F4\n                      <jats:sup>2<\/jats:sup>\n                    <\/jats:bold>\n                    demonstrates rapid adsorption kinetics with selectivities of 97\u2009:\u20093 for benzene over cyclohexane and 93\u2009:\u20097 for toluene over methylcyclohexane, while single\u2010crystal and powder X\u2010ray diffraction studies indicate that the selectivity is primarily governed by directed interactions between the electron\u2010deficient panels and aromatic guests.\n                  <\/jats:p>","DOI":"10.1002\/anie.202418877","type":"journal-article","created":{"date-parts":[[2024,11,8]],"date-time":"2024-11-08T03:54:02Z","timestamp":1731038042000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Fluorinated Squareimines for 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