2.2
Conclusion
In this chapter, the development of pseudorotaxanes based on crown ether
was introduced comprehensively. We discussed their synthesis, stimuli-responsive
movement, and their function and applications. Given the unique structures and
stimuli-responsive properties of crown ether and DBA, the dissociation and association of pseudorotaxanes makes them to be good candidates for molecular
switches, molecular locks and keys, and molecular logic gates. Chemists also have
studied their molecular machines in gels, which enable the functions of ion sensing,
nanovalves, and single-molecular imaging. Up to now, studies on pseudorotaxanes
have been widely explored. However, it is just the beginning.
Acknowledgments We thank NNSFC (21432004, 21672113, 21772099, 21861132001) for the
financial support.
References
1. Pedersen CJ (1967) Cyclic polyethers and their complexes with metal salts. J Am Chem Soc
89:7017–7036
2. Ji X, Yao Y, Li J, Yan X, Huang F (2013) A supramolecular cross-linked conjugated polymer
network for multiple fluorescent sensing. J Am Chem Soc 135:74–77
3. Wei P, Li J, Yan X, Zhou Q (2014) Metallosupramolecular poly[2]pseudorotaxane constructed
by metal coordination and crown-ether-based molecular recognition. Org Lett 16:126–129
4. Kim K (2002) Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem Soc Rev 31:96–107
5. Johnston AG, Leigh DA, Pritchard RJ, Deegan MD (2014) Facile synthesis and solid-state
structure of a benzylic amide [2]catenane. Angew Chem Int Ed 34:1209–1212
6. Niu Z, Slebodnick C, Gibson HW (2011) Pseudocryptand-type [3]Pseudorotaxane and “hookring” polypseudo[2]catenane based on a bis(m-phenylene)-32-crown-10 derivative and
bisparaquat derivatives. Org Lett 13:4616–4619
7. He L, Liu X, Liang J, Cong Y, Weng Z, Bu W (2015) Fluorescence responsive conjugated poly
(tetraphenylethene) and its morphological transition from micelle to vesicle. Chem Commun
51:7148–7151
8. Andrew TL, Swager TM (2011) Structure – property relationships for exciton transfer in
conjugated polymers. J Polym Sci B Polym Phys 49:476–498
9. Hu R, Maldonado JL, Rodriguez M, Deng C, Jim CKW, Lam JWY et al (2012) Luminogenic
materials constructed from tetraphenylethene building blocks: synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection. J Mater Chem 22:232–240
10. He L, Liang J, Cong Y, Chen X, Bu W (2014) Concentration and acid–base controllable
fluorescence of a metallosupramolecular polymer. Chem Commun 50:10841–10844
11. Wang Z, Chen S, Lam JWY, Qin W, Kwok RTK, Xie N et al (2013) Long-term fluorescent
cellular tracing by the aggregates of AIE bioconjugates. J Am Chem Soc 135:8238–8245
12. Lee S-Y, Ogawa A, Kanno M, Nakamoto H, Yasuda T, Watanabe M (2010) Nonhumidified
intermediate temperature fuel cells using protic ionic liquids. J Am Chem Soc 132:9764–9773
13. Pardo E, Train C, Gontard G, Boubekeur K, Fabelo O, Liu H et al (2011) High proton
conduction in a chiral ferromagnetic metal–organic quartz-like framework. J Am Chem Soc
133:15328–15331
14. Li L, He L, Wang B, Ge P, Jing L, Liu H et al (2018) Secondary dialkylammonium salt/crown
ether [2]pseudorotaxanes as nanostructured platforms for proton transport. Chem Commun
54:8092–8095
2 Polypseudorotaxanes Constructed by Crown Ethers
45
Conclusion
In this chapter, the development of pseudorotaxanes based on crown ether
was introduced comprehensively. We discussed their synthesis, stimuli-responsive
movement, and their function and applications. Given the unique structures and
stimuli-responsive properties of crown ether and DBA, the dissociation and association of pseudorotaxanes makes them to be good candidates for molecular
switches, molecular locks and keys, and molecular logic gates. Chemists also have
studied their molecular machines in gels, which enable the functions of ion sensing,
nanovalves, and single-molecular imaging. Up to now, studies on pseudorotaxanes
have been widely explored. However, it is just the beginning.
Acknowledgments We thank NNSFC (21432004, 21672113, 21772099, 21861132001) for the
financial support.
References
1. Pedersen CJ (1967) Cyclic polyethers and their complexes with metal salts. J Am Chem Soc
89:7017–7036
2. Ji X, Yao Y, Li J, Yan X, Huang F (2013) A supramolecular cross-linked conjugated polymer
network for multiple fluorescent sensing. J Am Chem Soc 135:74–77
3. Wei P, Li J, Yan X, Zhou Q (2014) Metallosupramolecular poly[2]pseudorotaxane constructed
by metal coordination and crown-ether-based molecular recognition. Org Lett 16:126–129
4. Kim K (2002) Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem Soc Rev 31:96–107
5. Johnston AG, Leigh DA, Pritchard RJ, Deegan MD (2014) Facile synthesis and solid-state
structure of a benzylic amide [2]catenane. Angew Chem Int Ed 34:1209–1212
6. Niu Z, Slebodnick C, Gibson HW (2011) Pseudocryptand-type [3]Pseudorotaxane and “hookring” polypseudo[2]catenane based on a bis(m-phenylene)-32-crown-10 derivative and
bisparaquat derivatives. Org Lett 13:4616–4619
7. He L, Liu X, Liang J, Cong Y, Weng Z, Bu W (2015) Fluorescence responsive conjugated poly
(tetraphenylethene) and its morphological transition from micelle to vesicle. Chem Commun
51:7148–7151
8. Andrew TL, Swager TM (2011) Structure – property relationships for exciton transfer in
conjugated polymers. J Polym Sci B Polym Phys 49:476–498
9. Hu R, Maldonado JL, Rodriguez M, Deng C, Jim CKW, Lam JWY et al (2012) Luminogenic
materials constructed from tetraphenylethene building blocks: synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection. J Mater Chem 22:232–240
10. He L, Liang J, Cong Y, Chen X, Bu W (2014) Concentration and acid–base controllable
fluorescence of a metallosupramolecular polymer. Chem Commun 50:10841–10844
11. Wang Z, Chen S, Lam JWY, Qin W, Kwok RTK, Xie N et al (2013) Long-term fluorescent
cellular tracing by the aggregates of AIE bioconjugates. J Am Chem Soc 135:8238–8245
12. Lee S-Y, Ogawa A, Kanno M, Nakamoto H, Yasuda T, Watanabe M (2010) Nonhumidified
intermediate temperature fuel cells using protic ionic liquids. J Am Chem Soc 132:9764–9773
13. Pardo E, Train C, Gontard G, Boubekeur K, Fabelo O, Liu H et al (2011) High proton
conduction in a chiral ferromagnetic metal–organic quartz-like framework. J Am Chem Soc
133:15328–15331
14. Li L, He L, Wang B, Ge P, Jing L, Liu H et al (2018) Secondary dialkylammonium salt/crown
ether [2]pseudorotaxanes as nanostructured platforms for proton transport. Chem Commun
54:8092–8095
2 Polypseudorotaxanes Constructed by Crown Ethers
45