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In this work, two pairs of diastereomers containing R\/S\u2010 binaphthyl and homochiral cholesteryl domains are synthesized, which provide multiple sites to encapsulate polyaromatic hydrocarbon through \u03c0\u2013\u03c0 and CH\u2013\u03c0 interactions. X\u2010ray structures and computational studies suggest the binaphthol derivatives feature CH\u2013\u03c0 folding into butterfly\u2010like open geometry, while binaphthylenediamine derivatives adopt closed geometry supported by van der Waals between cholesteryl domains. Driven by solvophobic forces, the building units self\u2010assemble into vesicles and nanofibers in the aqueous and methanol phases, respectively. Binaphthol derivatives selectively encapsulate pyrene by naphthalene domains in the vesicle phase, while binaphthylenediamine derivatives encapsulate pyrene by cholesteryl domains in the nanofiber phase. Density functional theory\u2010based calculations and circular dichroism spectra evidence the closed geometry of binaphthylenediamine derivatives facilitates a clamp\u2010type host to increase the affinity toward pyrene in spite of the strong solvation competition. This work unveils the diastereoselectivity in the chiral coassembly, deepening the understanding of the precise synthesis of functional chiroptical complexes.<\/jats:p>","DOI":"10.1002\/smll.202400089","type":"journal-article","created":{"date-parts":[[2024,4,29]],"date-time":"2024-04-29T07:06:46Z","timestamp":1714374406000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Diastereoselective Supramolecular Encapsulation and Chirality Transfer Between Cholesteryl Binaphthyl Conjugates and Polyaromatic Hydrocarbon"],"prefix":"10.1002","volume":"20","author":[{"given":"Qi","family":"Zhang","sequence":"first","affiliation":[{"name":"Key Laboratory of Colloid and Interface Chemistry of Ministry of Education School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aiyou","family":"Hao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Colloid and Interface Chemistry of Ministry of Education School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4302-3846","authenticated-orcid":false,"given":"Pengyao","family":"Xing","sequence":"additional","affiliation":[{"name":"Key Laboratory of Colloid and Interface Chemistry of Ministry of Education School of Chemistry and Chemical Engineering Shandong University  Jinan 250100 P. R. 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