Optical Resolution of the Water-Soluble Ti4(embonate)6 Cages for Enantioselective Recognition of Chiral Drugs

Optical Resolution of the Water-Soluble Ti4(embonate)6 Cages for Enantioselective Recognition of Chiral Drugs

Synergetic optical resolution and chiral amplification of tetrahedral Ti4L6 cages by enantiopure coordination cations have been realized in this work. Anionic ΔΔΔΔ-[Ti4L6] and ΛΛΛΛ-[Ti4L6] cages (L = embonate) have been completely resolved by enantiopure Λ-[Mn­(1R,2R-DCH)3] and Δ-[Mn­(1S,2S-DCH)3] c...

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Veröffentlicht in:Chemistry of materials 2018-11, Vol.30 (21), p.7769-7775
Hauptverfasser: He, Yan-Ping, Yuan, Lv-Bing, Song, Jin-Shuai, Chen, Guang-Hui, Lin, Qipu, Li, Chunsen, Zhang, Lei, Zhang, Jian
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container_end_page 7775
container_issue 21
container_start_page 7769
container_title Chemistry of materials
container_volume 30
creator He, Yan-Ping
Yuan, Lv-Bing
Song, Jin-Shuai
Chen, Guang-Hui
Lin, Qipu
Li, Chunsen
Zhang, Lei
Zhang, Jian
description Synergetic optical resolution and chiral amplification of tetrahedral Ti4L6 cages by enantiopure coordination cations have been realized in this work. Anionic ΔΔΔΔ-[Ti4L6] and ΛΛΛΛ-[Ti4L6] cages (L = embonate) have been completely resolved by enantiopure Λ-[Mn­(1R,2R-DCH)3] and Δ-[Mn­(1S,2S-DCH)3] cations, respectively. Accordingly, two homochiral compounds (PTC-108­(Δ) and PTC-108­(Λ)) with three-dimensional supramolecular architectures were formed, containing larger diamondoid cages. Such an unusual resolution process clearly shows the stepwise transfer of homochirality from an enantiopure molecule to a resolved hydrogen-bonding aggregation and a final homochiral framework. Moreover, the separated homochiral Ti4L6 cage presents enantioselective recognition toward chiral organic and pharmaceutical molecules. This work opens a novel resolution-dependent homochiral framework construction approach, and it also takes the homochiral tetrahedral Ti4L6 cages with high solubility and stability into promising enantioselective application.
doi_str_mv 10.1021/acs.chemmater.8b03174
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Anionic ΔΔΔΔ-[Ti4L6] and ΛΛΛΛ-[Ti4L6] cages (L = embonate) have been completely resolved by enantiopure Λ-[Mn­(1R,2R-DCH)3] and Δ-[Mn­(1S,2S-DCH)3] cations, respectively. Accordingly, two homochiral compounds (PTC-108­(Δ) and PTC-108­(Λ)) with three-dimensional supramolecular architectures were formed, containing larger diamondoid cages. Such an unusual resolution process clearly shows the stepwise transfer of homochirality from an enantiopure molecule to a resolved hydrogen-bonding aggregation and a final homochiral framework. Moreover, the separated homochiral Ti4L6 cage presents enantioselective recognition toward chiral organic and pharmaceutical molecules. 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