Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding

Yao, Huan1,2,3; Ke, Hua1,2; Zhang, Xiaobin4; Pan, San-Jiang1,2; Li, Ming-Shuang1,2; Yang, Liu-Pan1,2; Schreckenbach, Georg4; Jiang, Wei1,2

2018-10-17

10.1021/jacs.8b09157

Journal of the American Chemical Society   影响因子和分区

0002-7863

During the last half a century, great achievements have been made in molecular recognition in parallel with the invention of numerous synthetic receptors. However, the selective recognition of hydrophilic molecules in water remains a generally accepted challenge in supramolecular chemistry but is commonplace in nature. In an earlier Communication [Huang et al. J. Am. Chem. Soc. 2016, 138, 14550], we reported a pair of endo-functionalized molecular tubes that surprisingly prefer highly hydrophilic molecules over hydrophobic molecules of a similar size and shape. The hydrophobic effect and hydrogen bonding were proposed to be responsible, but their exact roles were not fully elucidated. In this Article, we present a thorough study on the binding behavior of these molecular tubes toward 44 hydrophilic molecules in water. Principal component analysis reveals that the binding strength is weakly correlated to the hydrophobicity, volume, surface area, and dipole moment of guests. Furthermore, molecular dynamics simulations show the hydrophobic effect through releasing the poorly hydrogen-bonded cavity water contributes to the binding of all the hydrophilic molecules, while hydrogen bonding differentiates these molecules and is thus the key to achieve a high selectivity toward certain hydrophilic molecules over other molecules with a similar size and shape. Therefore, a good guest for these molecular tubes should meet the following criteria: the hydrogen-bonding sites should be complementary, and the molecular volume should be large enough to expel all the cavity water but not too large to cause steric hindrance. This rule of thumb may also be used to design a selective receptor for certain hydrophilic molecules. Following these guidelines, a "best-fit" guest was found for the syn-configured molecular tube with a binding constant as high as 10(6) M-1.

SCI ; EI

英语

NI期刊

第一 ; 通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17213101]

Chemistry

Chemistry, Multidisciplinary

WOS:000447953600046

AMER CHEMICAL SOC

20184205945168

Hydrogen ; Hydrophilicity ; Hydrophobicity ; Molecular dynamics ; Molecular recognition ; Molecules ; Principal component analysis

Chemistry:801 ; Physical Chemistry:801.4 ; Chemical Products Generally:804 ; Mathematical Statistics:922.2 ; Physical Properties of Gases, Liquids and Solids:931.2 ; Atomic and Molecular Physics:931.3

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Harbin Inst Technol, Sch Chem & Chem Engn, Harbin 150001, Heilongjiang, Peoples R China
4.Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada

Yao, Huan,Ke, Hua,Zhang, Xiaobin,et al. Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding[J]. Journal of the American Chemical Society,2018,140(41):13466-13477.

Yao, Huan.,Ke, Hua.,Zhang, Xiaobin.,Pan, San-Jiang.,Li, Ming-Shuang.,...&Jiang, Wei.(2018).Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding.Journal of the American Chemical Society,140(41),13466-13477.

Yao, Huan,et al."Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding".Journal of the American Chemical Society 140.41(2018):13466-13477.