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In this context, porous organic polymers (POPs) have significant potential owing to the possibility of integrating shape\u2010persistent macrocyclic units with high guest selectivity. Here, we report the synthesis of a macrocyclic porous organic polymer (<jats:italic>np<\/jats:italic>\u2010POP) and the corresponding model compound by reacting the cyclotetrabenzil naphthalene octaketone macrocycle with 1,2,4,5\u2010tetraaminobenzene and 1,2\u2010diaminobenzene, respectively, under solvothermal conditions. Co\u2010crystallization of the macrocycle and the model compound with various solvent molecules revealed their size\u2010selective inclusion within the macrocycle. Building on this finding, the <jats:italic>np<\/jats:italic>\u2010POP with a hierarchical pore structure and a surface area of 579\u2005m<jats:sup>2<\/jats:sup>\u2009g<jats:sup>\u22121<\/jats:sup> showed solvent uptake strongly correlated with their kinetic diameters. Solvents with kinetic diameters below 0.6\u2005nm \u2013 such as acetonitrile and dichloromethane \u2013 showed high uptake capacities exceeding 7\u2005mmol\u2009g<jats:sup>\u22121<\/jats:sup>. Xylene separation tests revealed a high overall uptake (~34\u2005wt\u2009%), with <jats:italic>o<\/jats:italic>\u2010xylene displaying a significantly lower uptake (~10\u2005wt\u2009% less than other isomers), demonstrating the possibility of size and shape selective separation of organic solvents.<\/jats:p>","DOI":"10.1002\/anie.202423809","type":"journal-article","created":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T11:44:48Z","timestamp":1736768688000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Porous Organic Polymers Incorporating Shape\u2010Persistent Cyclobenzoin Macrocycles for Organic Solvent Separation"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7832-5716","authenticated-orcid":false,"given":"Timur","family":"Ashirov","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Fribourg  Chemin du Mus\u00e9e 9 CH-1700 Fribourg 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