Nanostructures Prepared from Self-Assembly of
23rd IUPAC Conference on Physical Organic Chemistry (ICPOC23) 3rd – 8th July 2016 • Sydney • Australia
Nanostructures Prepared from Self-Assembly of Pillararene-Based Amphiphiles and Supra-Amphiphiles F. Huang,* G. Yu, Y. Yao, X. Chi and K. Jie Department of Chemistry, Zhejiang University, Hangzhou 310027, China [email protected]
Inspired by the natural phospholipid bilayer nanostructure, which is an important part of the cell membrane, various functional groups were introduced into pillararene-based macrocyclic amphiphiles, endowing their self-assemblies with interesting applications.1,2 For example, we designed and synthesized an amphiphilic pillar[5]arene containing five amino groups as the hydrophilic head and five alkyl chains as the hydrophobic tail.1a It self-assembled into well-defined nanovesicles under neutral conditions in 1 minute, and gradually transformed into microtubes after standing for 4 months. The nanovesicles were used in the controlled release of small molecules and the microtubes could be used to adsorb TNT. Similarly, “sweet nanotubes” were obtained from self-assembly of a sugar-functionalized macrocyclic amphiphile.2b These sweet nanotubes were utilized as excellent cell glues to agglutinate and inhibit the motility of pathogenic cells E. coli. Pillararene-based host-guest interactions were employed to construct a series of supra-amphiphiles not only in organic solvent but also in water.3 For example, we constructed a novel supramolecular amphiphile based on a pillar[6]arene and an azobenzene-containing guest in an organic solvent, which underwent a photoresponsive threading-dethreading switch upon UV and visible light irradiation due to the trans−cis photoisomerization of the guest, accompanied by disassembly and assembly of the corresponding aggregates.3a
References 1.
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(a) Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 15712–15715; (b) Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F.* Acc. Chem. Res. 2012, 45, 1294–1308; (c) Yu, G.; Jie, K.; Huang, F.* Chem. Rev. 2015, 115, 7240–7303; (d) Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F.* Chem. Rev. 2015, 115, 7398–7501. (a) Yao, Y.; Xue, M.; Zhang, Z.; Zhang, M.; Wang, Y.; Huang, F.* Chem. Sci. 2013, 4, 3667–3672. (b) Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.; Gao, C.; Huang, F.* J. Am. Chem. Soc. 2013, 135, 10310–10313; (c) Jie, K.; Zhou, Y.; Yao, Y.; Huang, F.* Chem. Soc. Rev. 2015, 44, 3568–3587. (a) Yu, G.; Han, C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Liu, S.;* Huang, F.* J. Am. Chem. Soc. 2012, 134, 8711–8717; (b) Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 13248–13251; (c) Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 19489–19497; (d) Chi, X.; Ji, X.; Xia, D.; Huang, F.* J. Am. Chem. Soc. 2015, 137, 1440–1443; (e) Jie, K.; Zhou, Y.; Yao, Y.; Shi, B.; Huang, F.* J. Am. Chem. Soc. 2015, 137, 10472–10475.
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Nanostructures Prepared from Self-Assembly of Pillararene-Based Amphiphiles and Supra-Amphiphiles F. Huang,* G. Yu, Y. Yao, X. Chi and K. Jie Department of Chemistry, Zhejiang University, Hangzhou 310027, China [email protected]
Inspired by the natural phospholipid bilayer nanostructure, which is an important part of the cell membrane, various functional groups were introduced into pillararene-based macrocyclic amphiphiles, endowing their self-assemblies with interesting applications.1,2 For example, we designed and synthesized an amphiphilic pillar[5]arene containing five amino groups as the hydrophilic head and five alkyl chains as the hydrophobic tail.1a It self-assembled into well-defined nanovesicles under neutral conditions in 1 minute, and gradually transformed into microtubes after standing for 4 months. The nanovesicles were used in the controlled release of small molecules and the microtubes could be used to adsorb TNT. Similarly, “sweet nanotubes” were obtained from self-assembly of a sugar-functionalized macrocyclic amphiphile.2b These sweet nanotubes were utilized as excellent cell glues to agglutinate and inhibit the motility of pathogenic cells E. coli. Pillararene-based host-guest interactions were employed to construct a series of supra-amphiphiles not only in organic solvent but also in water.3 For example, we constructed a novel supramolecular amphiphile based on a pillar[6]arene and an azobenzene-containing guest in an organic solvent, which underwent a photoresponsive threading-dethreading switch upon UV and visible light irradiation due to the trans−cis photoisomerization of the guest, accompanied by disassembly and assembly of the corresponding aggregates.3a
References 1.
2.
3.
(a) Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 15712–15715; (b) Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F.* Acc. Chem. Res. 2012, 45, 1294–1308; (c) Yu, G.; Jie, K.; Huang, F.* Chem. Rev. 2015, 115, 7240–7303; (d) Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F.* Chem. Rev. 2015, 115, 7398–7501. (a) Yao, Y.; Xue, M.; Zhang, Z.; Zhang, M.; Wang, Y.; Huang, F.* Chem. Sci. 2013, 4, 3667–3672. (b) Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.; Gao, C.; Huang, F.* J. Am. Chem. Soc. 2013, 135, 10310–10313; (c) Jie, K.; Zhou, Y.; Yao, Y.; Huang, F.* Chem. Soc. Rev. 2015, 44, 3568–3587. (a) Yu, G.; Han, C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Liu, S.;* Huang, F.* J. Am. Chem. Soc. 2012, 134, 8711–8717; (b) Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 13248–13251; (c) Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F.* J. Am. Chem. Soc. 2012, 134, 19489–19497; (d) Chi, X.; Ji, X.; Xia, D.; Huang, F.* J. Am. Chem. Soc. 2015, 137, 1440–1443; (e) Jie, K.; Zhou, Y.; Yao, Y.; Shi, B.; Huang, F.* J. Am. Chem. Soc. 2015, 137, 10472–10475.
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