Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release

Run Zhao; Yu-Juan Zhou; Ke-Cheng Jie; Jie Yang; Sébastien Perrier; Fei-He Huang

doi:10.1007/s10118-019-2305-1

Your Location：

Home >

Browse articles >

Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release

ARTICLE | Updated：2019-09-27

- Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release
- Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release
- Chinese Journal of Polymer Science 2020年38卷第1期页码：1-8
- Affiliations：
  
  a.State Key Laboratory of Chemical Engineering, Center for Chemistry of High-Performance & Novel Materials, Department of Chemistry, Zhejiang University, Hangzhou 310027, China
  b.Department of Chemistry, The University of Warwick, Coventry CV4 7AL, UK
  c.Faculty of Pharmacy and Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC 3052, Australia
  d.Warwick Medical School, The University of Warwick, Coventry CV4 7AL, UK
- Author bio：
  
  J.Yang.38@warwick.ac.uk (J.Y.)
  S.Perrier@warwick.ac.uk (S.P.)
  fhuang@zju.edu.cn (F.H.H.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (No. 21861130352) and Newton Advanced Fellowships of The Royal Society (No. NAF\R10066).
- DOI：10.1007/s10118-019-2305-1
  中图分类号：
- 收稿：2019-04-26，
  
  修回：2019-5-23，
  
  录用：2019-5-25，
  
  网络首发：2019-09-27，
  
  纸质出版：2020-01
- Accepted：
Scan QR Code
Citation: Zhao, R.; Zhou, Y. J.; Jie, K. C.; Yang, J.; Perrier, S.; Huang, F. H. Fluorescent supramolecular polymersomes based on pillararene/paraquat molecular recognition for pH-controlled drug release. Chinese J. Polym. Sci. 2020, 38, 1–8

Run Zhao, Yu-Juan Zhou, Ke-Cheng Jie, et al. Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release[J]. Chinese Journal of Polymer Science, 2020, 38(1): 1-8.
Citation: Zhao, R.; Zhou, Y. J.; Jie, K. C.; Yang, J.; Perrier, S.; Huang, F. H. Fluorescent supramolecular polymersomes based on pillararene/paraquat molecular recognition for pH-controlled drug release. Chinese J. Polym. Sci. 2020, 38, 1–8 DOI： 10.1007/s10118-019-2305-1.

Run Zhao, Yu-Juan Zhou, Ke-Cheng Jie, et al. Fluorescent Supramolecular Polymersomes Based on Pillararene/Paraquat Molecular Recognition for pH-controlled Drug Release[J]. Chinese Journal of Polymer Science, 2020, 38(1): 1-8. DOI： 10.1007/s10118-019-2305-1.

摘要

Abstract

Researchers have put significant efforts on developing versatile fluorescent polymeric systems due to their promising biological/biomedical labelling

tracking

monitoring

imaging

and diagnostic applications. However

complicated organic/polymeric synthesis or post-modification of these functionalized platforms is still a big obstacle for their further application and thereby provides clear motivation for exploring alternative strategies for the design and fabrication of easily available fluorescent systems. The marriage of supramolecular polymers and fluorescent imaging can provide a facile and dynamic manner instead of tedious and time-consuming synthesis due to the dynamic and reversible nature of noncovalent interactions. Herein

based on water-soluble pillararene/paraquat molecular recognition

we successfully prepare two amphiphilic polypseudorotaxanes which can self-assemble into supramolecular polymersomes in water. These polymersomes can be reversibly destroyed and reformed by tuning the solution pH. Attributed to the aggregation-induced emission of tetraphenylethylene groups

intense fluorescence can be introduced into the obtained supramolecular polymersomes. Furthermore

pH-triggered release of an encapsulated water-insoluble drug (doxorubicin) from the self-assembled fluorescent supramolecular polymersomes is also investigated.

关键词

Keywords

references

Yang, Z.; He, Y.; Lee, J. H.; Park, N.; Suh, M.; Chae, W. S.; Cao, J.; Peng, X.; Jung, H.; Kang, C.; Kim, J. S . A self-calibrating bipartite viscosity sensor for mitochondria . J. Am. Chem. Soc. , 2013 . 135 9181 - 9185 . DOI: 10.1021/ja403851p http://doi.org/10.1021/ja403851p .

Yu, G.; Zhang, M.; Saha, M. L.; Mao, Z.; Chen, J.; Yao, Y.; Zhou, Z.; Liu, Y.; Gao, C.; Huang, F.; Chen, X.; Stang, P. J . Antitumor activity of a unique polymer that incorporates a fluorescent self-assembled metallacycle . J. Am. Chem. Soc. , 2017 . 139 15940 - 15949 . DOI: 10.1021/jacs.7b09224 http://doi.org/10.1021/jacs.7b09224 .

Peng, H. Q.; Sun, C. L.; Niu, L. Y.; Chen, Y. Z.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z . Supramolecular polymeric fluorescent nanoparticles based on quadruple hydrogen bonds . Adv. Funct. Mater. , 2016 . 26 5483 - 5489 . DOI: 10.1002/adfm.201600593 http://doi.org/10.1002/adfm.201600593 .

Sun, C. L.; Xu, J. F.; Chen, Y. Z.; Niu, L. Y.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z . Synthesis of a disulfide-bridged bispillar[5]arene and its application in supramolecular polymers . Polym. Chem. , 2016 . 7 2057 - 2061 . DOI: 10.1039/C6PY00148C http://doi.org/10.1039/C6PY00148C .

Yang, C.; Wang, X.; Huang, S.; Wang, M . Tunable Forster resonance energy transfer in colloidal nanoparticles composed of polycaprolactone-tethered donors and acceptors: enhanced near-infrared emission and compatibility for in vitro and in vivo bioimaging . Adv. Funct. Mater. , 2018 . 28 1705226 - 1705238 . DOI: 10.1002/adfm.v28.7 http://doi.org/10.1002/adfm.v28.7 .

Jiang, N.; Ahmed, R.; Rifat, A. A.; Guo, J.; Yin, Y.; Montelongo, Y.; Butt, H.; Yetisen, A. K . Functionalized flexible soft polymer optical fibers for laser photomedicine . Adv. Optical Mater. , 2018 . 6 1701118 - 1701127 . DOI: 10.1002/adom.v6.3 http://doi.org/10.1002/adom.v6.3 .

Sylvie, R.; Tânia, R.; Clarisse, R.; Daniela, M. C.; José, P. S. F.; Andreia, C. G.; Carlos, B.; Senentxu, L. M . Multifunctional platform based on electroactive polymers and silica nanoparticles for tissue engineering applications . Nanomaterials , 2018 . 8 933 - 952 . DOI: 10.3390/nano8110933 http://doi.org/10.3390/nano8110933 .

Robert, G.; Chen, Y. C.; Lee, J. W.; Soman, P.; Zorlutuna, P.; Nichol, J. W.; Bae, H.; Chen, S.; Khademhosseini, A . Microfabrication of complex porous tissue engineering scaffolds using 3D projection stereolithography . Biomaterials , 2012 . 33 3824 - 3834 . DOI: 10.1016/j.biomaterials.2012.01.048 http://doi.org/10.1016/j.biomaterials.2012.01.048 .

Wu, C.; Hansen, S. J.; Hou, Q.; Yu, J.; Zeigler, M.; Jin, Y.; Burnham, D. R.; McNeill, J. D.; Olson, J. M.; Chiu, D. T . Design of highly emissive polymer dot bioconjugates for in vivo tumor targeting . Angew. Chem. Int. Ed. , 2011 . 50 3430 - 3434 . DOI: 10.1002/anie.201007461 http://doi.org/10.1002/anie.201007461 .

Feng, W.; Jin, M.; Yang, K.; Pei, Y.; Pei, Z . Supramolecular delivery systems based on pillararenes . Chem. Commun. , 2018 . 54 13626 - 13640 . DOI: 10.1039/C8CC08252A http://doi.org/10.1039/C8CC08252A .

Reisch, A.; Heimburger, D.; Ernst, P.; Runser, A.; Didier, P.; Dujardin, D.; Klymchenko, A. S . Protein-sized dye-loaded polymer nanoparticles for free particle diffusion in cytosol . Adv. Funct. Mater. , 2018 . 28 1805157 - 1805166 . DOI: 10.1002/adfm.v28.48 http://doi.org/10.1002/adfm.v28.48 .

Lou, X. Y.; Yang, Y. W . Manipulating aggregation-induced emission with supramolecular macrocycles . Adv. Optical Mater. , 2018 . 6 1800668 - 1800692 . DOI: 10.1002/adom.v6.22 http://doi.org/10.1002/adom.v6.22 .

Liu, F.; Zhao, X.; Zhang, X.; Zhang, X.; Peng, J.; Yang, H.; Deng, K.; Ma, L.; Chang, C.; Wei, H . Fabrication of theranostic amphiphilic conjugated bottlebrush copolymers with alternating heterografts for cell imaging and anticancer drug delivery . Polym. Chem. , 2018 . 9 4866 - 4874 . DOI: 10.1039/C8PY01221K http://doi.org/10.1039/C8PY01221K .

Liu, X.; Zhu, J.; Ouyang, K.; Yan, Q . Peroxynitrite-biosignal-responsive polymer micelles as intracellular hypersensitive nanoprobes . Polym. Chem. , 2018 . 9 5075 - 5079 . DOI: 10.1039/C8PY01110A http://doi.org/10.1039/C8PY01110A .

Zhang, P.; Wang, H.; Hong, Y.; Yu, M.; Zeng, R.; Long, Y.; Chen, J . Selective visualization of endogenous hypochlorous acid in zebrafish during lipopolysaccharide-induced acute liver injury using a polymer micelles-based ratiometric fluorescent probe . Biosens. Bioelectron. , 2018 . 99 318 - 324 . DOI: 10.1016/j.bios.2017.08.001 http://doi.org/10.1016/j.bios.2017.08.001 .

Zhao, C.; Zhang, X.; Li, K.; Zhu, S.; Guo, Z.; Zhang, L.; Wang, F.; Fei, Q.; Luo, S.; Shi, P.; Tian, H.; Zhu, W. H . Forster resonance energy transfer switchable self-assembled micellar nanoprobe: ratiometric fluorescent trapping of endogenous H 2 S generation via fluvastatin-stimulated upregulation . J. Am. Chem. Soc. , 2015 . 137 8490 - 8498 . DOI: 10.1021/jacs.5b03248 http://doi.org/10.1021/jacs.5b03248 .

Rideau, E.; Wurm, F. R.; Landfester, K . Giant polymersomes from non-assisted film hydration of phosphate-based block copolymers . Polym. Chem. , 2018 . 9 5385 - 5394 . DOI: 10.1039/C8PY00992A http://doi.org/10.1039/C8PY00992A .

Zhang, N.; Chen, H.; Fan, Y.; Zhou, L.; Trepout, S.; Guo, J.; Li, M. H . Fluorescent polymersomes with aggregation-induced emission . ACS Nano , 2018 . 12 4025 - 4035 . DOI: 10.1021/acsnano.8b01755 http://doi.org/10.1021/acsnano.8b01755 .

Abdelmohsen, L. K. E.; Williams, A. D. S.; Pille, J.; Ozel, S. G.; Rikken, R. S. M.; Wilson, D. A.; van Hest, J. C. M . Formation of well-defined, functional nanotubes via osmotically induced shape transformation of biodegradable polymersomes . J. Am. Chem. Soc. , 2016 . 138 9353 - 9356 . DOI: 10.1021/jacs.6b03984 http://doi.org/10.1021/jacs.6b03984 .

Kulkarni, P. S.; Haldar, M. K.; Confeld, M. I.; Langaas, C. J.; Yang, X.; Qian, S. Y.; Mallik, S . Mitochondria-targeted fluorescent polymersomes for drug delivery to cancer cells . Polym. Chem. , 2016 . 7 4151 - 4154 . DOI: 10.1039/C6PY00623J http://doi.org/10.1039/C6PY00623J .

Bratton, B. P.; Shaevitz, J. W.; Gitai, Z.; Morgenstein, R. M . MreB polymers and curvature localization are enhanced by RodZ and predict E. coli 's cylindrical uniformity . Nat. Commun. , 2018 . 9 2797 .

Chang, D.; Huang, A.; Olsen, B. D . Kinetic effects on self-assembly and function of protein-polymer bioconjugates in thin films prepared by flow coating . Macromol. Rapid Commun. , 2017 . 38 1600449 - 1600454 . DOI: 10.1002/marc.v38.1 http://doi.org/10.1002/marc.v38.1 .

Thomas, C. S.; Olsen, B. D . Coil fraction-dependent phase behavior of a model globular protein-polymer diblock copolymer . Soft Matter , 2014 . 10 3093 - 3102 . DOI: 10.1039/C3SM52531G http://doi.org/10.1039/C3SM52531G .

Yu, G.; Zhao, R.; Shao, L.; Zhou, J.; Yang, J.; Huang, F.; Wu, D.; Tang, G.; Zhang, F.; Chen, X . Pillar[5]arene-based amphiphilic supramolecular brush copolymers: fabrication, controllable self-assembly and application in self-imaging targeted drug delivery . Polym. Chem. , 2016 . 7 6178 - 6188 . DOI: 10.1039/C6PY01402J http://doi.org/10.1039/C6PY01402J .

Jie, K.; Zhou, Y.; Ji, X . A pH-responsive amphiphilic supramolecular graft copolymer constructed by crown ether based molecular recognition . Polym. Chem. , 2015 . 6 218 - 222 . DOI: 10.1039/C4PY01072H http://doi.org/10.1039/C4PY01072H .

Wang, Y.; Sukhishvili, S. A . All-aqueous nanoprecipitation: Spontaneous formation of hydrogen-bonded nanoparticles and nanocapsules mediated by phase separation of poly( N -isopropylacrylamide) . Macromol. Rapid Commun. , 2017 . 38 1700242 - 1700246 . DOI: 10.1002/marc.v38.16 http://doi.org/10.1002/marc.v38.16 .

Wang, H.; Ji, X.; Li, Z.; Huang, F . Fluorescent supramolecular polymeric materials . Adv. Mater. , 2017 . 29 1606117 - 1606138 . DOI: 10.1002/adma.v29.14 http://doi.org/10.1002/adma.v29.14 .

Wang, R. F.; Peng, H. Q.; Chen, P. Z.; Niu, L. Y.; Gao, J. F.; Wu, L. Z.; Tung, C. H.; Chen, Y. Z.; Yang, Q. Z . A hydrogen-bonded-supramolecular-polymer-based nanoprobe for ratiometric oxygen sensing in living cells . Adv. Funct. Mater. , 2016 . 26 5419 - 5425 . DOI: 10.1002/adfm.201601831 http://doi.org/10.1002/adfm.201601831 .

Wang, W.; Han, J. J.; Wang, L. Q.; Li, L. S.; Shaw, W. J.; Li, A. D. Q . Dynamic π - π stacked molecular assemblies emit from green to red colors . Nano Lett. , 2003 . 3 455 - 458 . DOI: 10.1021/nl025976j http://doi.org/10.1021/nl025976j .

Lu, W.; Chan, M. C. W.; Cheung, K. K.; Che, C. M . π - π Interactions in organometallic systems. Crystal structures and spectroscopic properties of luminescent mono-, bi-, and trinuclear trans -cyclometalated platinum(II) complexes derived from 2,6-diphenylpyridine . Organometallics , 2001 . 20 2477 - 2486 . .

Nishizawa, S.; Kato, Y.; Teramae, N . Fluorescence sensing of anions via intramolecular excimer formation in a pyrophosphate-induced self-assembly of a pyrene-functionalized guanidinium receptor . J. Am. Chem. Soc. , 1999 . 121 9463 - 9464 . DOI: 10.1021/ja991497j http://doi.org/10.1021/ja991497j .

Yoshida, K.; Miyazaki, H.; Miura, Y.; Ooyama, Y.; Watanabe, S . Solid-surface fluorescence enhancement behavior of a benzofuranoquinol-type fluorescent host upon enclathration of alicyclic amines . Chem. Lett. , 1999 . 837 - 838 . .

Ban, Q.; Du, J.; Sun, W.; Chen, J.; Wu, S.; Kong, J . Intramolecular copper-containing hyperbranched polytriazole assemblies for label-free cellular bioimaging and redox-triggered copper complex delivery . Macromol. Rapid Commun. , 2018 . 39 1800171 - 1800176 . DOI: 10.1002/marc.v39.11 http://doi.org/10.1002/marc.v39.11 .

Wei, P.; Yan, X.; Huang, F . Supramolecular polymers constructed by orthogonal self-assembly based on host-guest and metal-ligand interactions . Chem. Soc. Rev. , 2015 . 44 815 - 832 . DOI: 10.1039/C4CS00327F http://doi.org/10.1039/C4CS00327F .

Hu, J.; Liu, S . Engineering responsive polymer building blocks with host-guest molecular recognition for functional applications . Acc. Chem. Res. , 2014 . 47 2084 - 2095 . DOI: 10.1021/ar5001007 http://doi.org/10.1021/ar5001007 .

Yang, H.; Yuan, B.; Zhang, X.; Scherman, O. A . Supramolecular chemistry at interfaces: host-guest interactions for fabricating multifunctional biointerfaces . Acc. Chem. Res. , 2014 . 47 2106 - 2115 . DOI: 10.1021/ar500105t http://doi.org/10.1021/ar500105t .

Zhang, M.; Yan, X.; Huang, F.; Niu, Z.; Gibson, H. W . Stimuli-responsive host-guest systems based on the recognition of cryptands by organic guests . Acc. Chem. Res. , 2014 . 47 1995 - 2005 . DOI: 10.1021/ar500046r http://doi.org/10.1021/ar500046r .

Zhang, D. W.; Zhao, X.; Li, Z. T . Aromatic amide and hydrazide foldamer-based responsive host-guest systems . Acc. Chem. Res. , 2014 . 47 1961 - 1970 . DOI: 10.1021/ar5000242 http://doi.org/10.1021/ar5000242 .

Yang, Y. W.; Sun, Y. L.; Song, N . Switchable host-guest systems on surfaces . Acc. Chem. Res. , 2014 . 47 1950 - 1960 . DOI: 10.1021/ar500022f http://doi.org/10.1021/ar500022f .

Cook, T. R.; Zheng, Y. R.; Stang, P. J . Metal-organic frameworks and self-assembled supramolecular coordination complexes: comparing and contrasting the design, synthesis, and functionality of metal-organic materials . Chem. Rev. , 2013 . 113 734 - 777 . DOI: 10.1021/cr3002824 http://doi.org/10.1021/cr3002824 .

Servant, A.; Qiu, F.; Mazza, M.; Kostarelos, K.; Nelson, B. J . Controlled in vivo swimming of a swarm of bacteria-like microrobotic flagella . Adv. Mater. , 2015 . 27 2981 - 2988 . DOI: 10.1002/adma.201404444 http://doi.org/10.1002/adma.201404444 .

Wang, H.; Su, W.; Wang, S.; Wang, X.; Liao, Z.; Kang, C.; Han, L.; Chang, J.; Wang, G.; Pu, P . Smart multifunctional core-shell nanospheres with drug and gene co-loaded for enhancing the therapeutic effect in a rat intracranial tumor model . Nanoscale , 2012 . 4 6501 - 6508 . DOI: 10.1039/c2nr31263h http://doi.org/10.1039/c2nr31263h .

Zhang, Y. M.; Li, Y. F.; Fang, H.; He, J. X.; Yong, B. R.; Yao, H.; Wei, T. B.; Lin, Q . Multi-stimuli-responsive supramolecular gel constructed by pillar[5]arene-based pseudorotaxanes for efficient detection and separation of multi-analytes in aqueous solution . Soft Matter , 2018 . 14 8529 - 8536 . DOI: 10.1039/C8SM01838C http://doi.org/10.1039/C8SM01838C .

Han, Y.; Tian, Y.; Li, Z.; Wang, F . Donor-acceptor-type supramolecular polymers on the basis of preorganized molecular tweezers/guest complexation . Chem. Soc. Rev. , 2018 . 47 5165 - 5176 . DOI: 10.1039/C7CS00802C http://doi.org/10.1039/C7CS00802C .

Wei, T. B.; Chen, J. F.; Cheng, X. B.; Li, H.; Han, B. B.; Yao, H.; Zhang, Y. M.; Lin, Q . Construction of stimuli-responsive supramolecular gel via bispillar[5]arene-based multiple interactions . Polym. Chem. , 2017 . 8 2005 - 2009 . DOI: 10.1039/C7PY00335H http://doi.org/10.1039/C7PY00335H .

Ma, X.; Tian, H . Stimuli-responsive supramolecular polymers in aqueous solution . Acc. Chem. Res. , 2014 . 47 1971 - 1981 . DOI: 10.1021/ar500033n http://doi.org/10.1021/ar500033n .

Qi, Z.; Schalley, C. A . Exploring macrocycles in functional supramolecular gels: from stimuli responsiveness to systems chemistry . Acc. Chem. Res. , 2014 . 47 2222 - 2233 . DOI: 10.1021/ar500193z http://doi.org/10.1021/ar500193z .

Ji, X. F.; Xia, D. Y.; Yan, X.; Wang, H.; Huang, F. H . Supramolecular polymer materials based on crown ether and pillararene host-guest recognition motifs . Acta Polymerica Sinica (in Chinese) , 2017 . 9 - 18 . .

Yang, J.; Shao, L.; Yuan, J.; Huang, F . Construction of a pillar[6]arene based water-soluble supramolecular pseudopolyrotaxane driven by cucurbit[8] uril-enhanced π - π interaction . Chem. Commun. , 2016 . 52 12510 - 12512 . DOI: 10.1039/C6CC07433B http://doi.org/10.1039/C6CC07433B .

Dhinakaran, M. K.; Gong, W.; Yin, Y.; Wajahat, A.; Kuang, X.; Wang, L.; Ning, G . Configuration-independent AIE-active supramole-cular polymers of cyanostilbene through the photo-stable host-guest interaction of pillar[5]arene . Polym. Chem. , 2017 . 8 5295 - 5302 . DOI: 10.1039/C7PY00845G http://doi.org/10.1039/C7PY00845G .

Wang, Y.; Lv, M. Z.; Song, N.; Liu, Z. J.; Wang, C.; Yang, Y. W . Dual-stimuli-responsive fluorescent supramolecular polymer based on a diselenium-bridged pillar[5]arene dimer and an AIE-active tetraphenylethylene guest . Macromolecules , 2017 . 50 5759 - 5766 . DOI: 10.1021/acs.macromol.7b01010 http://doi.org/10.1021/acs.macromol.7b01010 .

Hua, B.; Shao, L.; Zhang, Z.; Sun, J.; Yang, J . Pillar[6]arene/acridine orange host-guest complexes as colorimetric and fluorescence sensors for choline compounds and further application in monitoring enzymatic reactions . Sens. Actuators B , 2018 . 255 1430 - 1435 . DOI: 10.1016/j.snb.2017.08.141 http://doi.org/10.1016/j.snb.2017.08.141 .

Hu, X.; Wu, X.; Wang, S.; Chen, D.; Xia, W.; Lin, C.; Pan, Y.; Wang, L . Pillar[5]arene-based supramolecular polypseudorotaxane polymer networks constructed by orthogonal self-assembly . Polym. Chem. , 2013 . 4 4292 - 4297 . DOI: 10.1039/c3py00575e http://doi.org/10.1039/c3py00575e .

Li, E.; Jie, K.; Zhou, Y.; Zhao, R.; Huang, F . Post-synthetic modification of nonporous adaptive crystals of pillar[4]-arene[1]quinone by capturing vaporized amines . J. Am. Chem. Soc. , 2018 . 140 15070 - 15079 . DOI: 10.1021/jacs.8b10192 http://doi.org/10.1021/jacs.8b10192 .

Li, Z.; Zhang, Y.; Zhang, C.; Chen, L. J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H. B . Cross-linked supramolecular polymer gels constructed from discrete multi-pillar[5]arene metallacycles and their multiple stimuli-responsive behavior . J. Am. Chem. Soc. , 2014 . 136 8577 - 8589 . DOI: 10.1021/ja413047r http://doi.org/10.1021/ja413047r .

Xu, J. F.; Chen, Y. Z.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z . Dynamic covalent bond based on reversible [4+4] photocycloaddition of anthracene for construction of double-dynamic polymers . Org. Lett. , 2013 . 15 6148 - 6151 . DOI: 10.1021/ol403015s http://doi.org/10.1021/ol403015s .

Jie, K.; Zhou, Y.; Li, E.; Zhao, R.; Huang, F . Separation of aromatics/cyclic aliphatics by nonporous adaptive pillararene crystals . Angew. Chem. Int. Ed. , 2018 . 57 12845 - 12849 . DOI: 10.1002/anie.201808998 http://doi.org/10.1002/anie.201808998 .

Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H . A facile and efficient preparation of pillararenes and a pillarquinone . Angew. Chem. Int. Ed. , 2009 . 48 9721 - 9723 . DOI: 10.1002/anie.200904765 http://doi.org/10.1002/anie.200904765 .

Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y . Para -bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property . J. Am. Chem. Soc. , 2008 . 130 5022 - 5023 . DOI: 10.1021/ja711260m http://doi.org/10.1021/ja711260m .

Zhang, H.; Liu, Z.; Zhao, Y . Pillararene-based self-assembled amphiphiles . Chem. Soc. Rev. , 2018 . 47 5491 - 5528 . DOI: 10.1039/C8CS00037A http://doi.org/10.1039/C8CS00037A .

Yu, G.; Yang, J.; Fu, X.; Wang, Z.; Shao, L.; Mao, Z.; Liu, Y.; Yang, Z.; Zhang, F.; Fan, W.; Song, J.; Zhou, Z.; Gao, C.; Huang, F.; Chen, X . A supramolecular hybrid material constructed from graphene oxide and a pillar[6]arene-based host-guest complex as an ultrasound and photoacoustic signal nanoampli . Mater. Horiz. , 2018 . 5 429 - 435 . DOI: 10.1039/C8MH00128F http://doi.org/10.1039/C8MH00128F .

Jie, K.; Zhou, Y.; Li, E.; Li, Z.; Zhao, R.; Huang, F . Reversible iodine capture by nonporous pillar[6]arene crystals . J. Am. Chem. Soc. , 2017 . 139 15320 - 15323 . DOI: 10.1021/jacs.7b09850 http://doi.org/10.1021/jacs.7b09850 .

Jie, K.; Liu, M.; Zhou, Y.; Little, M. A.; Bonakala, S.; S. Chong, Y.; Stephenson, A.; Chen, L.; Huang, F.; Cooper, A. I . Styrene purification by guest-induced restructuring of pillar[6]arene . J. Am. Chem. Soc. , 2017 . 139 2908 - 2911 . DOI: 10.1021/jacs.6b13300 http://doi.org/10.1021/jacs.6b13300 .

Dong, R.; Zhou, Y.; Huang, X.; Zhu, X.; Lu, Y.; Shen, J . Functional supramolecular polymers for biomedical applications . Adv. Mater. , 2015 . 27 498 - 526 . DOI: 10.1002/adma.v27.3 http://doi.org/10.1002/adma.v27.3 .

Mei, J.; Huang, Y.; Tian, H . Progress and trends in AIE-based bioprobes: a brief overview . ACS Appl. Mater. Interfaces , 2018 . 10 12217 - 12261 . DOI: 10.1021/acsami.7b14343 http://doi.org/10.1021/acsami.7b14343 .

Furue, R.; Nishimoto, T.; Park, I. S.; Lee, J.; Yasuda, T . Aggregation-induced delayed fluorescence based on donor/acceptor-tethered Janus carborane triads: unique photophysical properties of nondoped OLEDs . Angew. Chem. Int. Ed. , 2016 . 55 7171 - 7175 . DOI: 10.1002/anie.201603232 http://doi.org/10.1002/anie.201603232 .

Yan, X.; Wang, M.; Cook, T. R.; Zhang, M.; Saha, M. L.; Zhou, Z.; Li, X.; Huang, F.; Stang, P. J . Light-emitting superstructures with anion effect: coordination-driven self-assembly of pure tetraphenylethylene metallacycles and metallacages . J. Am. Chem. Soc. , 2016 . 138 4580 - 4588 . DOI: 10.1021/jacs.6b00846 http://doi.org/10.1021/jacs.6b00846 .

Li, K.; Liu, B . Polymer-encapsulated organic nanoparticles for fluorescence and photoacoustic imaging . Chem. Soc. Rev. , 2014 . 43 6570 - 6597 . DOI: 10.1039/C4CS00014E http://doi.org/10.1039/C4CS00014E .

Luo, J.; Xie, Z. J.; Lam, W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z . Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole . Chem. Commun. , 2001 . 1740 - 1741 . DOI: 10.1039/B105159H http://doi.org/10.1039/B105159H .

Ji, X.; Li, Y.; Wang, H.; Zhao, R.; Tang, G.; Huang, F . Facile construction of fluorescent polymeric aggregates with various morphologies by self-assembly of supramolecular amphiphilic graft copolymers . Polym. Chem. , 2015 . 28 5021 - 5025 . DOI: 10.1039/C5PY00801H http://doi.org/10.1039/C5PY00801H .

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

A Fluorescent Supramolecular Crosslinked Polymer Gel Formed by Crown Ether Based Host-Guest Interactions and Aggregation Induced Emission

Boosting Blood-Brain Barrier Crossing with a Mannosylated Nanocarrier

Composition-dependent Emission in Bifuran-based Polyester Films Doped with Aggregation-induced Emission Luminogen for Information Storage and Encryption

Multicomponent Polymerization of Alkynes, Amines, and Benzaldehyde toward Main-chain Charged Aggregation-induced Emission Polyelectrolytes

Experimental Investigation of Graphene and TiO2 Reinforced Poly(vinyl alcohol)-based Fiber Metal Laminates