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However, achieving precise control over the chiral self\u2010sorted structures and their functional properties for the bioinspired supramolecular systems still remains a challenge, not to mention realizing dynamically reversible regulation. Herein, we report an unprecedented saucer[4]arene\u2010based charge transfer (CT) cocrystal system with dynamically reversible chiral self\u2010sorting synergistically induced by chiral triangular macrocycle and organic vapors. It displays efficient chain length\u2010selective vapochromism toward alkyl ketones due to precise modulation of optical properties by vapor\u2010induced diverse structural transformations. Experimental and theoretical studies reveal that the unique vapochromic behavior is mainly attributed to the formation of homo\u2010 or heterochiral self\u2010sorted assemblies with different alkyl ketone guests, which differ dramatically in solid\u2010state superstructures and CT interactions, thus influencing their optical properties. This work highlights the essential role of chiral self\u2010sorting in controlling the functional properties of synthetic supramolecular systems, and the rarely seen controllable chiral self\u2010sorting at the solid\u2010vapor interface deepens the understanding of efficient vapochromic sensors.<\/jats:p>","DOI":"10.1002\/anie.202407095","type":"journal-article","created":{"date-parts":[[2024,4,24]],"date-time":"2024-04-24T22:03:21Z","timestamp":1713996201000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":47,"title":["Macrocycle\u2010Based Charge Transfer Cocrystals with Dynamically Reversible Chiral Self\u2010Sorting Display Chain Length\u2010Selective Vapochromism to Alkyl Ketones"],"prefix":"10.1002","volume":"63","author":[{"given":"Meng\u2010Jie","family":"Gu","sequence":"first","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute 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