Triptycene-Derived Macrocyclic Arenes
6
From Calixarenes to Helicarenes
Ying Han and Chuan-Feng Chen
Contents
6.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139
6.2 Triptycene-Derived Calixarenes and Analogues . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 141
6.2.1 Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . 141
6.2.2 Structures in Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150
6.2.3 Structures in Solid State . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . 154
6.2.4 Molecular Recognition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 157
6.2.5 Molecular Self-Assembly . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 162
6.3 Helicarenes: New Chiral Macrocyclic Arenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166
6.3.1 Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . 167
6.3.2 Structural Characterization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169
6.3.3 Applications in Molecular Recognitions and Self-Assemblies . . . . . . . . . . . . . . . . . . 171
6.4 Conclusion and Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 178
6.1
Introduction
Since Pedersen first reported the synthesis of crown ethers and their cation-complexing
properties in 1967, the development of new class of macrocyclic hosts has always been
one of the most important topics in host-guest chemistry, and also supramolecular
chemistry during the last half century. Consequently, various macrocyclic hosts [1–4]
including crown ethers, cryptands, cyclodextrins, cavitands, cyclophanes,
Y. Han
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
C.-F. Chen (*)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
University of Chinese Academy of Sciences, Beijing, China
e-mail: cchen@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_7
139
6
From Calixarenes to Helicarenes
Ying Han and Chuan-Feng Chen
Contents
6.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 139
6.2 Triptycene-Derived Calixarenes and Analogues . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 141
6.2.1 Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . 141
6.2.2 Structures in Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150
6.2.3 Structures in Solid State . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . 154
6.2.4 Molecular Recognition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 157
6.2.5 Molecular Self-Assembly . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 162
6.3 Helicarenes: New Chiral Macrocyclic Arenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166
6.3.1 Synthesis . . . . . . . . . . . . . .. . . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . . . . . . . . . . .. . . . 167
6.3.2 Structural Characterization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169
6.3.3 Applications in Molecular Recognitions and Self-Assemblies . . . . . . . . . . . . . . . . . . 171
6.4 Conclusion and Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 178
6.1
Introduction
Since Pedersen first reported the synthesis of crown ethers and their cation-complexing
properties in 1967, the development of new class of macrocyclic hosts has always been
one of the most important topics in host-guest chemistry, and also supramolecular
chemistry during the last half century. Consequently, various macrocyclic hosts [1–4]
including crown ethers, cryptands, cyclodextrins, cavitands, cyclophanes,
Y. Han
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
C.-F. Chen (*)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular
Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China
University of Chinese Academy of Sciences, Beijing, China
e-mail: cchen@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_7
139