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

Wang，Song Meng1; Wang，Yan Fang1; Huang，Liping1; Zheng，Li Shuo1; Nian，Hao1; Zheng，Yu Tao1; Yao，Huan2; Jiang，Wei1; Wang，Xiaoping1; Yang，Liu Pan2

2023-12-01

10.1038/s41467-023-41390-8

Nature Communications   Impact Factor & Quartile

2041-1723

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.

SCI

English

NI Journal Papers

First ; Corresponding

National Natural Science Foundation of China-Yunnan Joint Fund[21801125];National Natural Science Foundation of China-Yunnan Joint Fund[22125105];National Natural Science Foundation of China-Yunnan Joint Fund[22301127];

Science & Technology - Other Topics

Multidisciplinary Sciences

WOS:001087583700022

NATURE PORTFOLIO

2-s2.0-85171178612

Scopus

1.Department of Chemistry,Southern University of Science and Technology,Shenzhen,Xueyuan Blvd 1088,518055,China
2.School of Pharmaceutical Science,Hengyang Medical School,University of South China,Hengyang,Hunan,421001,China

Wang，Song Meng,Wang，Yan Fang,Huang，Liping,et al. Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity[J]. Nature Communications,2023,14(1).

Wang，Song Meng.,Wang，Yan Fang.,Huang，Liping.,Zheng，Li Shuo.,Nian，Hao.,...&Yang，Liu Pan.(2023).Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity.Nature Communications,14(1).

Wang，Song Meng,et al."Chiral recognition of neutral guests by chiral naphthotubes with a bis-thiourea endo-functionalized cavity".Nature Communications 14.1(2023).