Skip to main content
SpringerLink
Log in

Monoacrylated cyclodextrin via “click” reaction and copolymerization with N-isopropylacrylamide: guest controlled solution properties

  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Mono-(1 H-1, 2, 3-triazol-4-yl) (methyl) 2-methylacryl-β-cyclodextrin (CD) 3 is synthesized by microwave assisted `click´ reaction of propargyl (meth) acrylate and mono-(6-azido-6-deoxy)-β-CD using Cu (I) catalysis. Free radical copolymerizations of monomer 3 with N-isopropylacrylamide 5 (NIPAAM) of different portions are carried out. The properties of polymers are characterized by use of gel permeation chromatography (GPC), dynamic light scattering (DLS) and turbidity measurements. The Lower Critical Solution Temperatures (LCSTs) of the copolymers with different portions of NIPAAM and influence of guest molecules addition by adamantly carboxylate and adamantly methyl methacrylate are evaluated.

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
Scheme 2
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Lehn JM (1995) Supramolecular Chemistr. Wiley-VCH, New York 1995

    Book  Google Scholar 

  2. Raymo FM, Stoddart JF (1999) Chem Rev 99:1643 doi:10.1021/cr970081q

    Article  CAS  Google Scholar 

  3. Szejtli J (1998) Chem Rev 98:1743 doi:10.1021/cr970022c

    Article  CAS  Google Scholar 

  4. Wenz G, Han BH, Müller A (2006) Chem Rev 106:782 doi:10.1021/cr970027+

    Article  CAS  Google Scholar 

  5. Harada A, Kamachi M (1990) Macromolecules 23:2821 doi:10.1021/ma00212a039

    Article  CAS  Google Scholar 

  6. Harada A, Li J, Kamachi M (1992) Nature 356:325 doi:10.1038/356325a0

    Article  CAS  Google Scholar 

  7. Wenz G, Keller B (1992) Angew Chem Int Ed Engl 31:197 doi:10.1002/anie.199201971

    Article  Google Scholar 

  8. Harada A, Okada M, Kamachi M (1995) Macromolecules 28:8406 doi:10.1021/ma00128a060

    Article  CAS  Google Scholar 

  9. Harada A, Kawaguchi Y, Nishiyama T, Kamachi M (1997) Macromol Rapid Commun 18:535 doi:10.1002/marc.1997.030180701

    Article  CAS  Google Scholar 

  10. Ohga K, Takashima Y, Takahashi H, Kawaguchi Y, Yamaguchi H, Harada A (2005) Macromolecules 38:5897 doi:10.1021/ma0508606

    Article  CAS  Google Scholar 

  11. Huang L, Allen E, Tonelli AE (1999) Polymer (Guildf) 40:3211 doi:10.1016/S0032-3861(98)00529-1

    Article  CAS  Google Scholar 

  12. Rusa CC, Tonelli AE (2000) Macromolecules 33:1813 doi:10.1021/ma991883l

    Article  CAS  Google Scholar 

  13. Rusa CC, Luca C, Tonelli AE (2001) Macromolecules 34:1318 doi:10.1021/ma001868c

    Article  CAS  Google Scholar 

  14. Lu J, Mirau PA, Tonelli AE (2001) Macromolecules 34:3276 doi:10.1021/ma001820z

    Article  CAS  Google Scholar 

  15. Choi SW, Ritter H (2004) J. Macromol. Sci Part A 42:321 doi:10.1081/MA-200050463

    Article  Google Scholar 

  16. Ritter H, Sadowski O, Tepper E (2003) Angew. Chem. Int. Ed. 42:3171; Corrigendum: Ritter H, Sadowski O, Tepper E (2005). Angew Chem Int Ed 44:6099 doi:10.1002/anie.200590128

    Google Scholar 

  17. Schmitz S, Ritter H (2005) Angew Chem Int Ed 44:5658 doi:10.1002/anie.200501374

    Article  CAS  Google Scholar 

  18. Kretschmann O, Choi SW, Miyauchi M, Tomatsu I, Harada A, Ritter H (2006) Angew Chem Int Ed 45:4361 doi:10.1002/anie.200504539

    Article  Google Scholar 

  19. Lewis WG, Green LG, Grynszpan F, Radic Z, Carlier PR, Taylor P et al (2002) Angew Chem Int Ed 41:1053

    CAS  Google Scholar 

  20. Fazio F, Bryan MC, Blixt O, Paulson JC, Wong CH (2002) Am. Chem. Soc. 124:14397 doi:10.1021/ja020887u

    Article  CAS  Google Scholar 

  21. Bryan MC, Fazio F, Lee HK, Huang CY, Chang A, Best MD et al (2004) J Am Chem Soc 126:8640 doi:10.1021/ja048433f

    Article  CAS  Google Scholar 

  22. Collman JP, Devaraj NK, Chidsey CED (2004) Langmuir 20:1051 doi:10.1021/la0362977

    Article  CAS  Google Scholar 

  23. Wu P, Feldman AK, Nugent AK, Hawker CJ, Scheel A, Voit B et al (2004) Angew Chem Int Ed 43:3928 doi:10.1002/anie.200454078

    Article  CAS  Google Scholar 

  24. Helms B, Mynar JL, Hawker CJ, Fréchet JMJ (2004) J Am Chem Soc 126:15020 doi:10.1021/ja044744e

    Article  CAS  Google Scholar 

  25. Huisgen R, Knorr R, Mobius L, Szeimies G (1965) Chem Ber 98:4014 doi:10.1002/cber.19650981228

    Article  CAS  Google Scholar 

  26. Ryu EH, Zhao Y (2005) Org Lett 7:1035 doi:10.1021/ol047468h

    Article  CAS  Google Scholar 

  27. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596 doi:10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4

    Article  CAS  Google Scholar 

  28. Hoogenboom R, Moore BC, Schubert US (2006) Chem Comm 4010

  29. Barr L, Lincoln S, Easton C (2005) J Supramol Chem 17:547–555

    Article  CAS  Google Scholar 

  30. Kraus T, Budesinsky M, Zavada J (1998) Collect Czech Chem Commun 63:534 doi:10.1135/cccc19980534

    Article  CAS  Google Scholar 

  31. Roehri-Steockel C, Dangles O, Brouillard R (1997) Tetrahedron Lett 38:1551 doi:10.1016/S0040-4039(97)00145-7

    Article  Google Scholar 

  32. Munteanu M, Choi SW, Ritter H Macromolecules (submitted)

  33. Heskins M, Guillet JE (1968) J Macromol Sci Chem A2:1441 doi:10.1080/10601326808051910

    Article  Google Scholar 

  34. Schild HG (1992) Prog Polym Sci 17:163 doi:10.1016/0079-6700(92)90023-R

    Article  CAS  Google Scholar 

  35. Ohashi H, Hiraoka Y, Yamaguchi T (2006) Macromolecules 39:2614 doi:10.1021/ma052509q

    Article  CAS  Google Scholar 

  36. Wang HD, Chu LY, Yu XQ, Xie R, Yang M, Xu D et al (2007) Ind Eng Chem Res 46:1511 doi:10.1021/ie061265a

    Article  CAS  Google Scholar 

  37. Taylor LD, Cerankowski LD (1975) J. Polym Sci., Polym Chem Ed 13:2551

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial supports by the Deutsche Forschungsgemeinschaft (DFG) are greatly acknowledged.

Author information

Authors and Affiliations

  1. Heinrich-Heine-Universität Düsseldorf, Institute für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Präparative Polymerchemie, Universitätsstraße 1, 40225, Düsseldorf, Germany

    SooWhan Choi, Maricica Munteanu & Helmut Ritter

Authors
  1. SooWhan Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maricica Munteanu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Helmut Ritter
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Helmut Ritter.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Choi, S., Munteanu, M. & Ritter, H. Monoacrylated cyclodextrin via “click” reaction and copolymerization with N-isopropylacrylamide: guest controlled solution properties. J Polym Res 16, 389–394 (2009). https://doi.org/10.1007/s10965-008-9240-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10965-008-9240-0

Keywords

Search

Navigation