Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity

Song-Meng Wang, Yan-Fang Wang, Liping Huang, Li-Shuo Zheng, Hao Nian, Yu-Tao Zheng, Huan Yao, Wei Jiang (), Xiaoping Wang () and Liu-Pan Yang ()
Additional contact information
Song-Meng Wang: Southern University of Science and Technology
Yan-Fang Wang: Southern University of Science and Technology
Liping Huang: Southern University of Science and Technology
Li-Shuo Zheng: Southern University of Science and Technology
Hao Nian: Southern University of Science and Technology
Yu-Tao Zheng: Southern University of Science and Technology
Huan Yao: Hengyang Medical School, University of South China
Wei Jiang: Southern University of Science and Technology
Xiaoping Wang: Southern University of Science and Technology
Liu-Pan Yang: Hengyang Medical School, University of South China

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Developing chiral receptors with an endo-functionalized cavity for chiral recognition is of great significance in the field of molecular recognition. This study presents two pairs of chiral naphthotubes containing a bis-thiourea endo-functionalized cavity. Each chiral naphthotube has two homochiral centers which were fixed adjacent to the thiourea groups, causing the skeleton and thiourea groups to twist enantiomerically through chiral transfer. These chiral naphthotubes are highly effective at enantiomerically recognizing various neutral chiral molecules with an enantioselectivity up to 17.0. Furthermore, the mechanism of the chiral recognition has been revealed to be originated from differences in multiple non-covalent interactions. Various factors, such as the shape of cavities, substituents of guests, flexibility of host and binding modes are demonstrated to contribute to creating differences in the non-covalent interactions. Additionally, the driving force behind enantioselectivity is mainly attributed to enthalpic differences, and enthalpy -entropy compensation has also been observed to influence enantioselectivity.

Date: 2023
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-023-41390-8 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-41390-8

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-023-41390-8

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().