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DLS results and SEM images imply that these pillararene macrocycles self\u2010assemble in acetonitrile solution, while X\u2010ray crystallographic evidence suggests solvent\u2010dependent assembly in the solid state. The nature of the sulfur substituents decorating the rim of the pillararene controls binding affinities towards organic guest encapsulations within the cavity and dictates metal\u2010ion binding properties through the formation of favorable S\u2212M<jats:sup>2+<\/jats:sup> coordination bonds outside the cavity, as determined by <jats:sup>1<\/jats:sup>H NMR and fluorescence spectroscopic experiments. Addition of a dinitrile guest containing a bis\u2010triazole benzene spacer (<jats:bold>btn<\/jats:bold>) induced formation of pseudorotaxane host\u2010guest complexes. Fluorescence emission signals from these discrete macrocycles were significantly attenuated in the presence of either Hg<jats:sup>2+<\/jats:sup> or Cu<jats:sup>2+<\/jats:sup> in solution. Analogous titrations utilizing the corresponding pseudorotaxanes alter the binding selectivity and improve fluorescence sensing sensitivity. In addition, preliminary liquid\u2010liquid extraction studies indicate that the macrocycles facilitate the transfer of Cu<jats:sup>2+<\/jats:sup> from the aqueous to the organic phase in comparison to extraction without pillar[5]arene ligands.<\/jats:p>","DOI":"10.1002\/asia.202300913","type":"journal-article","created":{"date-parts":[[2023,11,16]],"date-time":"2023-11-16T10:44:52Z","timestamp":1700131492000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Switchable Metal\u2010Ion Selectivity in Sulfur\u2010Functionalised Pillar[5]arenes and Their Host\u2010Guest Complexes"],"prefix":"10.1002","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4980-3133","authenticated-orcid":false,"given":"Bunyaporn","family":"Todee","sequence":"first","affiliation":[{"name":"Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC) Faculty of Sciense Mahidol University  Bangkok 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