Water-Soluble Aromatic Crown Ethers
1
From Molecular Recognition to Molecular Assembly
Ling Chen and Yu Liu
Contents
1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.2 The Binding Behaviors of Crown Ethers in Aqueous Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
1.3 Sulfonated Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
1.4 Carboxylated Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
1.5 Molecular Assembly Based on Water-Soluble Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . 18
1.6 Conclusions and Outlook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
1.1
Introduction
After the serendipitous discovery by Pedersen [1], crown ethers have been
widely applied as brine separators, phase-transfer catalysts [2], and chiral
sensors [3]. The simplest crown ethers are heterocycles with cyclic oligomers
of ethyleneoxy. Although dioxane is compliant to this definition, it is not
realized as a crown ether due to small cavity. The other crown ethers with
simple chemical formula of (–CH 2 CH 2 O–) n in which n ! 3 are soluble in both
water and organic solvents, they can bind small guests containing metal ions,
L. Chen
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, China
Y. Liu (*)
College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University,
Tianjin, China
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China
e-mail: yuliu@nankai.edu.cn
© Springer Nature Singapore Pte Ltd. 2020
Y. Liu et al. (eds.), Handbook of Macrocyclic Supramolecular Assembly,
https://doi.org/10.1007/978-981-15-2686-2_2
3
1
From Molecular Recognition to Molecular Assembly
Ling Chen and Yu Liu
Contents
1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3
1.2 The Binding Behaviors of Crown Ethers in Aqueous Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
1.3 Sulfonated Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
1.4 Carboxylated Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
1.5 Molecular Assembly Based on Water-Soluble Aromatic Crown Ethers . . . . . . . . . . . . . . . . . . 18
1.6 Conclusions and Outlook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
1.1
Introduction
After the serendipitous discovery by Pedersen [1], crown ethers have been
widely applied as brine separators, phase-transfer catalysts [2], and chiral
sensors [3]. The simplest crown ethers are heterocycles with cyclic oligomers
of ethyleneoxy. Although dioxane is compliant to this definition, it is not
realized as a crown ether due to small cavity. The other crown ethers with
simple chemical formula of (–CH 2 CH 2 O–) n in which n ! 3 are soluble in both
water and organic solvents, they can bind small guests containing metal ions,
L. Chen
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, China
Y. Liu (*)
College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University,
Tianjin, China
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, China
e-mail: yuliu@nankai.edu.cn
© Springer Nature Singapore Pte Ltd. 2020
Y. Liu et al. (eds.), Handbook of Macrocyclic Supramolecular Assembly,
https://doi.org/10.1007/978-981-15-2686-2_2
3