Skip to main content
SpringerLink
Log in

pH-responsive amphiphilic H-shaped supramolecular copolymer via the inclusion complexation between β-cyclodextrin and adamantane

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

pH-responsive amphiphilic H-shaped copolymer was prepared by the supramolecular self-assembly between β-cyclodextrin-graft-poly(2-(N,N-diethylamino)ethyl methacrylate) (β-CD-(PDEAEMA)2) and bi-adamantyl terminated poly(ε-caprolactone) (Ad-PCL-Ad). β-CD-(PDEAEMA)2 was synthesized by click reaction of alkynyl-modified β-CD with azide PDEAEMA (PDEAEMA-N3). Ad-PCL-Ad was synthesized by the DCC reaction of bi-hydroxyl terminated PCL (HO-PCL-OH) with adamantaneacetic acid. The supramolecular copolymer can self-assemble into micelles in water at room temperature. The micellization and pH-responsivity of the amphiphilic copolymer solution were investigated by transmittance, dynamic light scattering spectrophotometer, and transmission electron microscopy in water. Investigation shows that the micelles’ sizes can be adjusted through the alteration of the pH values of solutions and the supramolecular copolymer will have the potential applications in biomedical field.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Dupin D, Armes SP, Syuji F (2009) Stimulus-responsive liquid marbles. J Am Chem Soc 131:5386–5387. doi:10.1021/ja901641v

    Article  CAS  Google Scholar 

  2. Orakdogen N (2011) pH-responsive swelling behavior, elasticity and molecular characteristics of poly(N, N dimethylaminoethyl methacrylate) gels at various initial monomer concentrations. Polym Bull 67:1347–1366. doi:10.1007/s00289-011-0559-z

    Article  CAS  Google Scholar 

  3. Ma YH, Tang YQ, Billingham NC et al (2003) Synthesis of biocompatible, stimuli-responsive, physical gels based on ABA triblock copolymers. Biomacromolecules 4:864–868. doi:10.1021/bm034118u

    Article  CAS  Google Scholar 

  4. Martin TJ, Prochazka K, Munk P et al (1996) pH-dependent micellization of poly (2-vinyl pyridine)-block-poly(ethylene oxide). Macromolecules 29:6071–6073. doi:10.1021/ma960629f

    Article  CAS  Google Scholar 

  5. Mori H, Kato I, Saito S et al (2010) Proline-based block copolymers displaying upper and lower critical solution temperatures. Macromolecules 43:1289–1298. doi:10.1021/ma902002b

    Article  CAS  Google Scholar 

  6. Plamper FA, Schmalz A, Ballauff M et al (2007) Tuning the thermoresponsiveness of weak polyelectrolytes by pH and light: lower and upper critical-solution temperature of poly (N, N-dimethylaminoethyl methacrylate). J Am Chem Soc 129:14538–14539. doi:10.1021/ja074720i

    Article  CAS  Google Scholar 

  7. Meléndez-Ortiz HI, Bucio E (2008) Radiation synthesis of a thermo-pH responsive binary graft copolymer (PP-g-DMAEMA)-g-NIPAAm by a two step method. Polym Bull 61:619–629. doi:10.1007/s00289-008-0982-y

    Article  Google Scholar 

  8. Lee AS, Butun V, Vamvakaki M et al (2002) Structure of pH-dependent block copolymer micelles: charge and ionic strength dependence. Macromolecules 35:8540–8551. doi:10.1021/ma0114842

    Article  CAS  Google Scholar 

  9. Asayama S, Maruyama A, Cho CS et al (1997) Design of comb-type polyamine copolymers for a novel pH-sensitive DNA carrier. Bioconj Chem 8:833–838. doi:10.1021/bc970097n

    Article  CAS  Google Scholar 

  10. Du L, Liao SJ, Khatib HA et al (2009) Controlled-access hollow mechanized silica nanocontainers. J Am Chem Soc 131:15136–15142. doi:10.1021/ja904982j

    Article  CAS  Google Scholar 

  11. Meng H, Xue M, Xia T et al (2010) Autonomous in vitro anticancer drug release from mesoporous silica nanoparticles by pH-sensitive nanovalves. J Am Chem Soc 132:12690–12697. doi:10.1021/ja104501a

    Article  CAS  Google Scholar 

  12. Setijadi E, Tao L, Liu JQ et al (2009) Biodegradable star polymers functionalized with β-cyclodextrin inclusion complexes. Biomacromolecules 10:2699–2707. doi:10.1021/bm900646g

    Article  CAS  Google Scholar 

  13. Kolb HC, Finn MG, Sharpless KB (2001) Click Chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004–2021. doi:10.1002/1521-3773(20010601)40:11<2004:AID-ANIE2004>3.0.CO;2-5

    Article  CAS  Google Scholar 

  14. Shi GY, Yang LP, Pan CY (2008) Synthesis and characterization of well-defined polystyrene and poly(ε-caprolactone) hetero eight-shaped copolymers. J Polym Sci Part A Polym Chem 46:6496–6508. doi:10.1002/pola.22959

    Article  CAS  Google Scholar 

  15. Zeng Q, Li ZA, Li Z et al (2007) Convenient attachment of highly polar azo chromophore moieties to disubstituted polyacetylene through polymer reactions by using “click” chemistry. Macromolecules 40:5634–5637. doi:10.1021/ma070846o

    Article  CAS  Google Scholar 

  16. Yuan WZ, Zhao ZD, Gu SY et al (2010) Synthesis, characterization, and properties of amphiphilic chitosan copolymers with mixed side chains by click chemistry. J Polym Sci Part A Polym Chem 48:3476–3486. doi:10.1002/pola.24136

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the financial support of National Key Technology R&D Program (2012BAI15B06) and National Basic Research Program of China (973 Program: 2011CB013805).

Author information

Authors and Affiliations

  1. Institute of Nano and Bio-polymeric Materials, School of Materials Science and Engineering, Tongji University, Shanghai, 201804, People’s Republic of China

    Weizhong Yuan, Hui Zou, Wen Guo, Tianbin Ren & Jie Ren

  2. Key Laboratory of Advanced Civil Engineering Materials of Ministry of Education, Shanghai, 201804, People’s Republic of China

    Weizhong Yuan, Tianbin Ren & Jie Ren

Authors
  1. Weizhong Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hui Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wen Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tianbin Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jie Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Weizhong Yuan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yuan, W., Zou, H., Guo, W. et al. pH-responsive amphiphilic H-shaped supramolecular copolymer via the inclusion complexation between β-cyclodextrin and adamantane. Polym. Bull. 70, 2257–2267 (2013). https://doi.org/10.1007/s00289-013-0947-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-013-0947-7

Keywords

Search

Navigation