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Consequently, the selective synthesis of a specific stereoisomer becomes much more challenging. To address this problem, we co\u2010crystallized poly(ethylene glycol) and a diastereomeric ring molecule, pillar[5]arene, in the solid state. The co\u2010crystallization formed polypseudorotaxanes with a high diastereomeric excess (ca. 88\u2009% <jats:italic>de<\/jats:italic>), meaning that polypseudorotaxanes containing (<jats:italic>S<\/jats:italic>, <jats:italic>pS<\/jats:italic>) stereoisomer pillar[5]arene rings were synthesized selectively. By contrast, in solution and evaporation systems, the selectivity remained low (ca. 10\u2009% <jats:italic>de<\/jats:italic>). The results suggested that the packing effect by the co\u2010crystallization contributed to the denser assembly of ring molecules on the polymeric chain, resulting in the diastereoselective formation. High diastereoselectivity was also observed even in higher\u2010molecular\u2010weight poly(ethylene glycol)s. These selectivities arose from the cooperative effects of the ring molecules on the polymeric chain, which were supported by calculating the stabilization energy.<\/jats:p>","DOI":"10.1002\/anie.202420115","type":"journal-article","created":{"date-parts":[[2024,12,10]],"date-time":"2024-12-10T03:35:03Z","timestamp":1733801703000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Diastereoselective Polypseudorotaxane Formation with Planar Chiral Pillar[5]arenes via Co\u2010crystallization Processes"],"prefix":"10.1002","volume":"64","author":[{"given":"Kiichi","family":"Yasuzawa","sequence":"first","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keisuke","family":"Wada","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shixin","family":"Fa","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"},{"name":"School of Chemistry and Chemical Engineering Northwestern Polytechnical University  Xi'an Shaanxi 710072 P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuuya","family":"Nagata","sequence":"additional","affiliation":[{"name":"WPI Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University  Kita 21 Nishi 10 Kita-ku Sapporo 060-0810 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5348-5521","authenticated-orcid":false,"given":"Kenichi","family":"Kato","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shunsuke","family":"Ohtani","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Motohiro","family":"Mizuno","sequence":"additional","affiliation":[{"name":"NanoMaterials Research Institute (NanoMaRi) Kanazawa University  Kakuma-machi Kanazawa 920-1192 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4464-0347","authenticated-orcid":false,"given":"Tomoki","family":"Ogoshi","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura Nishikyo-ku Kyoto 615-8510 Japan"},{"name":"WPI Nano Life Science Institute (WPI-NanoLSI) Kanazawa University  Kakuma-machi Kanazawa 920-1192 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,2]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300599"},{"key":"e_1_2_8_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300599"},{"key":"e_1_2_8_2_1","unstructured":"\u00a0"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00198a084"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0000978"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900162q"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00354"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00952A"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.2183\/pjab.99.025"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00026a004"},{"key":"e_1_2_8_11_2","first-page":"364","volume":"21","author":"Wulff G.","year":"1991","journal-title":"Chem. 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However the enantio- and diasteroselective synthesis of topological polymers has not yet been achieved."},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/b705458k"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202114759"},{"key":"e_1_2_8_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202114759"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic200850r"},{"key":"e_1_2_8_31_1","unstructured":"The selective synthesis of [2] and [3]rotaxanes have been achieved using sophisticated strategies so far. 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optimize the co-crystallization conditions we changed the amount of PEG compared with P[5]a\u20131(Figure\u2005S44\u201353 Supplementary discussion)."},{"key":"e_1_2_8_87_1","unstructured":"CHCl3and methanol were used as solvents for the co-crystallization because CHCl3serves as a good solvent for pillar[5]arene while methanol is a poor solvent and they are easily miscible. Most importantly neither CHCl3nor methanol acts as a guest molecule for pillar[5]arene which ensures that they do not interfere with the co-crystallization of other guest molecules. Detailed discussion is described in Supporting Information (Figure\u2005S41)."},{"key":"e_1_2_8_88_1","unstructured":"Although these references support the role of chloroform as a complexation-promoting solvent for pillar[5]arenes polypseudorotaxane was not obtained in the solution system:"},{"key":"e_1_2_8_89_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC01968G"},{"key":"e_1_2_8_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.5b02515"},{"key":"e_1_2_8_91_1","unstructured":"We need to explain the reason why different solvents were used for the CD measurements of the polypseudorotaxane and the mixture of P[5]a\u20131and PEG. Due to the weak binding affinity between P[5]a\u20131and PEG polypseudorotaxane dissociated immediately when it dissolved in solvents (Figure\u2005S7c\u2013i d\u2013i). We conducted CD measurements of the polypseudorotaxanes in 1 2-dichloroethane. In 1 2-dichloroethane PEG was rapidly released however 1 2-dichloroethane can be subsequently captured by P[5]a\u20131 because 1 2-dichloroethane is a guest solvent for the P[5]a\u20131(Figure\u2005S7c\u2013i). The quick complexation with 1 2-dichloroethane memorized the chirality in the polypseudorotaxane state (Figure\u2005S7c\u2013ii) thus performing CD measurements immediately after dissolving the polypseudorotaxane in 1 2-dichloroethane allows for capturing the chirality derived from the pseudorotaxane state (Figure\u2005S7c\u2013iii). On the other hand in CHCl3 PEG was rapidly released and CHCl3cannot be captured by P[5]a\u20131 because CHCl3is too big to be a guest (Figure\u2005S7d\u2013i) resulting in the loss of the selectivity obtained by the co-crystallization immediately after dissolving in CHCl3(Figure\u2005S7d\u2013ii iii and S8\u20132). Therefore we conducted CD measurements of the polypseudorotaxanes in 1 2-dichloroethane. Regarding the CD measurements of the mixture of P[5]a\u20131and PEG we used CHCl3as a measuring solvent to investigate the chirality of the mixture solution before the co-crystallization (Figure\u2005S7a) and compare it with the obtained polypseudorotaxane crystals (Figure\u2005S7b). We also conducted the CD measurements of the mixture of P[5]a\u20131and PEG in 1 2-dichloroethane at equilibrium state however the diastereomeric excess was also small (Figure\u2005S3\u20132)."},{"key":"e_1_2_8_92_1","unstructured":"The reason why the polypseudorotaxanepS-rich rings rather thanpR-rich rings were obtained was because of the large energy differences among polypsedorotaxane diastereomers. In our previous reports [12c][3]pseudorotaxane with twopSforms P[5]a\u20131 was diastereoselectively obtained because thepS-rich [3]pseudorotaxane was energetically more stable than the other diastereomers [(S pS) (S pR)] and [(S pR) (S pR)] and the energy differences among the three diastereomers were large enough to result in selectivity. Thus for polypseudorotaxanes with large numbers of ring molecules pS-rich polypseudorotaxanes have an energetic advantage overpR-rich polypseudorotaxanes."},{"key":"e_1_2_8_93_1","unstructured":"We evaluated the chirality induction of the complex crystals by measuring CD spectrum immediately after dissolving the crystals in 1 2-dichloroethane. However it was unavoidable to have time lags between dissolving and measurements. Therefore we anticipate that diastereomer excess of the polypseudorotaxane would be higher than the data obtained by CD measurements in solution (88\u2009%de)."},{"key":"e_1_2_8_94_1","unstructured":"The small binding affinity between oligo(ethylene glycol)s and P[5]a\u20131and the low stability of the complex crystals to washing with water caused the difficulty in determining accurate host\u2013guest complex ratios and confirmation of reproducibility. However forPEG-400-OH we confirmed that 2.5 rings on average were arranged on one PEG chain with good reproducibility. Because the molecular weights of tetra(ethylene glycol) and penta(ethylene glycol) are approximately half that ofPEG-400-OH their complex polycrystals with P[5]a\u20131can be considered as a mixture of [2]pseudorotaxane and [3]pseudorotaxane."},{"key":"e_1_2_8_95_1","unstructured":"An upfield shift of the13C peak of the complex (orange square) compared to neat PEG attributed to the aromatic shielding effect of P[5]a\u20131 and a downfield shift of the P[5]a\u20131carbon signal assigned to CH2(Figure\u20056c\u2013iv green square) due to the deshielding effect provided us the evidences for polypseudorotaxane 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