Application of Anion-π Interaction on
Supramolecular Self-Assembly
10
De-Xian Wang
Contents
10.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253
10.2 Theoretical Study of Anion-π Interactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 254
10.3 Representative Experimental Evidences of Anion-π Interactions . . . . . . . . . . . . . . . . . . . . . . 256
10.4 Anion-Templated Self-Assembly . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 260
10.5 Self-Assembly with Anion as Primary Building Blocks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
10.5.1 Self-Assembly with Electron-Deficient Arenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
10.5.2 Self-Assembly with Macrocyclic Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 264
10.6 Self-Assembly with Anions as Secondary Building Blocks . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
10.7 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 272
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273
10.1 Introduction
The study of anion-π interactions should be dated to 1993, when Schneider and
coworkers described the attractive interaction between negative species and polarizable aryl parts [1]. There are no successive reports after that. Almost 10 years later
in 2002, Mascal [2], Deyà [3], and Alkorta [4] at the same time published their
independent theoretical studies on energetical favorable interaction between anions
and typical electron-deficient aromatics such as triazine, hexafluorobenzene, and
perfluoroaromatic compounds. Deyà also termed this interaction as anion-π interaction, reassembling its electrostatic antipode cation-π interaction. A rapid development of anion-π interactions has been witnessed ever since. Various computational
studies have been conducted to confirm existence and probe the nature of anion-π
interactions. Subsequent experimental efforts, either through incorporating simple
D.-X. Wang (*)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
e-mail: dxwang@iccas.ac.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_11
253
Supramolecular Self-Assembly
10
De-Xian Wang
Contents
10.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253
10.2 Theoretical Study of Anion-π Interactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 254
10.3 Representative Experimental Evidences of Anion-π Interactions . . . . . . . . . . . . . . . . . . . . . . 256
10.4 Anion-Templated Self-Assembly . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 260
10.5 Self-Assembly with Anion as Primary Building Blocks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
10.5.1 Self-Assembly with Electron-Deficient Arenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 262
10.5.2 Self-Assembly with Macrocyclic Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 264
10.6 Self-Assembly with Anions as Secondary Building Blocks . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
10.7 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 272
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273
10.1 Introduction
The study of anion-π interactions should be dated to 1993, when Schneider and
coworkers described the attractive interaction between negative species and polarizable aryl parts [1]. There are no successive reports after that. Almost 10 years later
in 2002, Mascal [2], Deyà [3], and Alkorta [4] at the same time published their
independent theoretical studies on energetical favorable interaction between anions
and typical electron-deficient aromatics such as triazine, hexafluorobenzene, and
perfluoroaromatic compounds. Deyà also termed this interaction as anion-π interaction, reassembling its electrostatic antipode cation-π interaction. A rapid development of anion-π interactions has been witnessed ever since. Various computational
studies have been conducted to confirm existence and probe the nature of anion-π
interactions. Subsequent experimental efforts, either through incorporating simple
D.-X. Wang (*)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
e-mail: dxwang@iccas.ac.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_11
253