Enantioselective Recognition of Functional Organic Molecules in Water by Biomimetic Macrocyclic Hosts

Yang, Xiran1,2; Jiang, Wei1,2

2024-01-31

10.1021/jacs.3c11492

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   影响因子和分区

0002-7863

1520-5126

Enantioselective recognition of functional organic molecules in water is routine in nature but remains a formidable challenge for synthetic hosts. Here, we reported two pairs of chiral naphthotubes with chiral centers located in the neighborhood of the inward-directing amide groups. These naphthotubes, with a chiral twisted cavity, show highly enantioselective recognition in water to a wide scope of organic molecules (90 chiral guests). The highest enantioselectivity of 34 was achieved with neotame. Small differences between all of the noncovalent interactions shielded in the hydrophobic cavity were revealed to be responsible for the enantioselective recognition in water, which is different from the traditional views. Moreover, these hosts can differentiate the analogues of aspartame using fluorescence spectroscopy. These chiral naphthotubes have made unprecedented achievements in enantioselective recognition, providing the basis for their applications in chiral analysis and separations.

SCI

英语

NI期刊

第一 ; 通讯

National Science Fund for Distinguished Young Scholars[2022.12] ; National Natural Science Foundation of China[22125105] ; Shenzhen "Pengcheng Scholar", Guangdong High-Level Personnel of Special Support Program[2019TX05C157] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:001158980300001

AMER CHEMICAL SOC

Web of Science

1.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol SUSTech, Dept Chem, Shenzhen 518055, Peoples R China

Yang, Xiran,Jiang, Wei. Enantioselective Recognition of Functional Organic Molecules in Water by Biomimetic Macrocyclic Hosts[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2024,146(6).

Yang, Xiran,&Jiang, Wei.(2024).Enantioselective Recognition of Functional Organic Molecules in Water by Biomimetic Macrocyclic Hosts.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,146(6).

Yang, Xiran,et al."Enantioselective Recognition of Functional Organic Molecules in Water by Biomimetic Macrocyclic Hosts".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 146.6(2024).