Hostname: page-component-78c5997874-g7gxr Total loading time: 0 Render date: 2024-11-13T10:56:02.768Z Has data issue: false hasContentIssue false
  • English
  • Français

Redox-responsive supramolecular polymer based on β-cyclodextrin and ferrocene-decorated main chain of PAA

Published online by Cambridge University Press:  06 October 2015

Wenping Guo  and
Zhongli Lei
Wenping Guo
Affiliation:
Key Laboratory of Applied Surface and Colloid Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an Shaanxi 710062, China
Zhongli Lei*
Affiliation:
Key Laboratory of Applied Surface and Colloid Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an Shaanxi 710062, China
*
a)Address all correspondence to this author. e-mail: [email protected]
Get access

Abstract

Herein, we present a method for introducing β-cyclodextrin (β-CD) and Ferrocene (Fc) into the main chain of poly(acrylic acid) (PAA) to fabricate a novel supramolecular polymer, which was investigated by Fourier transform infrared spectroscopy and 1H Nuclear Magnetic Resonance (1H NMR). This polymer can self-assemble into interesting nanoparticles in aqueous solution. The redox-responsive Fc–CD host–guest interactions endow these nanoparticles with unique self-degradable and self-healable features under redox potential control. This redox behavior of the supramolecular polymer would open up an approach for redox-controlled biological materials with great application potential.

Keywords

supramolecular polymernanoparticleshost–guest interactionsredox-responsive
Type
Articles
Information
Journal of Materials Research , Volume 30 , Issue 21 , 13 November 2015 , pp. 3201 - 3210
Copyright
Copyright © Materials Research Society 2015 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Footnotes

Contributing Editor: Tao Xie

References

REFERENCES

Dong, S.Y., Luo, Y., Yan, X.Z., Zheng, B., Ding, X., Yu, Y.H., Ma, Z., Zhao, Q.L., and Huang, F.H.: A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition. Angew. Chem., Int. Ed. 50, 1905 (2011).CrossRefGoogle ScholarPubMed
Yan, Q., Wang, J.B., Yin, Y.W., and Yuan, J.Y.: Breathing polymersomes: CO2-tuning membrane permeability for size-selective release, separation, and reaction. Angew. Chem., Int. Ed. 52, 5070 (2013).CrossRefGoogle ScholarPubMed
Nakahata, M., Takashima, Y., Yamaguchi, H., and Harada, A.: Redox-responsive self-healing materials formed from host-guest polymers. Nat. Commun. 2, 511 (2011).Google Scholar
Yan, Q., Hu, J., Zhou, R., Ju, Y., Yin, Y.W., and Yuan, J.Y.: Visible light-responsive micelles formed from dialkoxyanthracene-containing block copolymers. Chem. Commun. 48, 1913 (2012).Google Scholar
Kumar, S., Tong, X., Dory, Y.L., Lepage, M., and Zhao, Y.: A CO2-switchable polymer brush for reversible capture and release of proteins. Chem. Commun. 49, 90 (2013).Google Scholar
Moughton, A.O. and O'Reilly, R.K.: Thermally induced micelle to vesicle morphology transition for a charged chain end diblock copolymer. Chem. Commun. 46, 1091 (2010).CrossRefGoogle ScholarPubMed
Rodriguez-Hernandez, J. and Lecommandoux, S.: Reversible inside-out micellization of pH-responsive and water-soluble vesicles based on polypeptide diblock copolymers. J. Am. Chem. Soc. 127, 2026 (2005).Google Scholar
Yan, X.Z., Wang, F., Zheng, B., and Huang, F.H.: Stimuli-responsive supramolecular polymeric materials. Chem. Soc. Rev. 41, 6042 (2012).Google Scholar
Mura, S., Nicolas, J., and Couvreur, P.: Stimuli-responsive nanocarriers for drug delivery. Nat. Mater. 12, 991 (2013).Google Scholar
Sun, R.L., Wang, L., Yu, H.J., Chen, Y.S., Huang, J., and Tong, R.B.: Molecular recognition and sensing based on ferrocene derivatives and ferrocene-based polymers. Organometallics 33, 4560 (2014).Google Scholar
Ahn, S.k., Kasi, R.M., Kim, S.C., Sharma, N., and Zhou, Y.X.: Stimli-responsive polymer gels. Soft Matter 4, 1151 (2008).Google Scholar
Shankar, R., Ghosh, T.K., and Spontak, R.J.: Dielectric elastomers as next-generation polymeric actuators. Soft Matter 3, 1116 (2007).Google Scholar
Peng, L., Feng, A.C., Huo, M., and Yuan, J.Y.: Ferrocene-based supramolecular structures and their applications in electrochemical responsive systems. Chem. Commun. 50, 13005 (2014).Google Scholar
Schneider, H.J. and Yatsimirsky, A.K.: Selectivity in supramolecular host-guest complexes. Chem. Soc. Rev. 37, 263 (2008).CrossRefGoogle ScholarPubMed
Seward, E.M., Hopkins, R.B., Sauerer, W., Tam, S.W., and Diederich, F.: Redox-dependent binding ability of a flavin cyclophane in aqueous solution: Hydrophobic stacking versus cavity-inclusion complexation. J. Am. Chem. Soc. 112, 1783 (1990).Google Scholar
Wang, Y., Mendoza, S., and Kaifer, A.E.: Electrochemical reduction of cobaltocenium in the presence of β-cyclodextrin. Inorg. Chem. 37, 7 (1998).Google Scholar
Chan-Thaw, C.E., Villa, A., Prati, L., and Thomas, A.: Triazine-based polymers as nanostructured supports for the liquid-phase oxidation of alcohols. Chem. Eur. J. 3, 1052 (1997).Google Scholar
Whittell, G.R., Hager, M.D., Schubert, U.S., and Manners, I.: Functional soft materials from metallopolymers and metallosupramolecular polymers. Nat. Mater. 10, 176 (2011).Google Scholar
Matsue, T., Evans, D.H., Osa, T., and Kobayashi, N.: Electron-transfer reactions associated with host-guest complexation. Oxidation of ferrocenecarboxylic acid in the presence of beta-cyclodextrin. J. Am. Chem. Soc. 107, 3411 (1985).Google Scholar
Jones, M.C. and Leroux, J.C.: Polymeric micelles-a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 48, 101 (1999).Google Scholar
Torchilin, V.P.: Structure and design of polymeric surfactant-based drug delivery systems. J. Controlled Release 3, 137 (2001).Google Scholar
Yan, X.Z., Xu, D.H., Chi, X.D., Chen, J.Z., Dong, S.Y., Ding, X., Yu, Y.H., and Huang, F.H.: A multiresponsive, shape-persistent, and elastic supramolecular polymer network gel constructed by orthogonal self-assembly. Adv. Mater. 24, 362 (2012).Google Scholar
Groger, G., Meyer-Zaika, W., Bottcher, C., Grohn, F., Ruthard, C., and Schmuck, C.: Switchable supramolecular polymers from the self-assembly of a small monomer with two orthogonal binding interactions. J. Am. Chem. Soc. 133, 8961 (2011).Google Scholar
Kumpfer, J.R. and Rowan, S.J.: Thermo-, photo-, and chemo-responsive shape-memory properties from photo-cross-linked metallo-supramolecular polymers. J. Am. Chem. Soc. 133, 12866 (2011).Google Scholar
Yan, Q., Yuan, J.Y., Cai, Z.N., Xin, Y., Kang, Y., and Yin, Y.W.: Voltage-responsive vesicles based on orthogonal assembly of two homopolymers. J. Am. Chem. Soc. 132, 9268 (2010).Google Scholar
Liu, L.C., Rui, L.L., Gao, Y., and Zhang, W.A.: Self-assembly and disassembly of a redox-responsive ferrocene-containing amphiphilic block copolymer for controlled release. Polym. Chem. 6, 1817 (2015).Google Scholar
Liu, Y.L. and Chuo, T.W.: Self-healing polymers based on thermally reversible Diels–Alder chemistry. Polym. Chem. 4, 2194 (2013).Google Scholar
Elbert, J., Gallei, M., Rvttiger, C., Brunsen, A., Didzoleit, H., Stvhn, B., and Rehahn, M.: Ferrocene polymers for switchable surface wettability. Organometallics 32, 5873 (2013).Google Scholar
Schmidt, B.V., Hetzer, M., Ritter, H., and Barner-Kowollik, C.: Complex macromolecular architecture design via cyclodextrin host/guest complexes. Prog. Polym. Sci. 39, 235 (2014).CrossRefGoogle Scholar
Wei, K.C., Li, J., Chen, G.S., and Jiang, M.: Dual molecular recognition leading to a protein-polymer conjugate and further self-assembly. ACS Macro Lett. 2, 278 (2013).Google Scholar
Zuo, F., Luo, C., Ding, X.B., Zheng, Z., Cheng, X., and Peng, Y.: Redox-responsive inclusion complexation between β-cyclodextrin and ferrocene-functionalized poly(N-isopropylacrylamide) and its effect on the solution properties of this polymer. Supramol. Chem. 20, 559 (2008).Google Scholar
Tian, Z.C., Chen, C., and Allcock, H.R.: Synthesis and assembly of novel poly(organophosphazene) structures based on noncovalent “host-guest” inclusion complexation. Macromolecules 47, 1065 (2014).Google Scholar