Skip to main content
SpringerLink
Log in

Covalently β-cyclodextrin modified single-walled carbon nanotubes: a novel artificial receptor synthesized by ‘click’ chemistry

  • Brief Communication
  • Published:
Journal of Nanoparticle Research Aims and scope Submit manuscript

Abstract

Novel β-cyclodextrin covalently modified single-walled carbon nanotubes have been synthesized via a ‘click’ coupling reaction. The product was fully characterized with Raman, FTIR, XRD, UV-Vis-NIR spectra as well as TEM and TGA measurements. The effective functionalization via ‘click’ coupling has set up a facile and versatile route for modular preparation of SWNTs based functional materials. The inclusion complexation behavior of this artificial receptor with quinine has been investigated in aqueous solution by fluorescence spectroscopy.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

References

  • Agag T, Takeichi T (2001) Novel benzoxazine monomers containing p-phenyl propargyl ether: polymerization of monomers and properties of polybenzoxazines. Macromolecules 34:7257–7263

    Article  CAS  Google Scholar 

  • Bahr JL, Tour JM (2001) Highly functionalized carbon nanotubes using in situ generated diazonium compounds. Chem Mater 13:3823–3824

    Article  CAS  Google Scholar 

  • Binder WH, Sachsenhofer R (2007) ‘Click’ chemistry in polymer and materials science. Macromol Rapid Commun 28:15–54

    Article  CAS  Google Scholar 

  • Chen Y, Wang Y-L, Rassat A, Sinaÿ P, Zhao Y, Zhang Y-M (2006) Synthesis of water-soluble 2-alkylcyclodextrin–C60 conjugates and their inclusion complexation in aqueous solution. Tetrahedron 62:2045–2049

    Article  CAS  Google Scholar 

  • Dresselhaus MS, Dresselhaus G, Avouris P (eds) (2001) Carbon nanotubes: synthesis, structure, properties and applications. Springer, Berlin

    Google Scholar 

  • Feazell RP, Nakayama-Ratchford N, Dai H, Lippard SJ (2007) Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design. J Am Chem Soc 129:8438–8439

    Article  CAS  Google Scholar 

  • Furtado CA, Kim UJ, Gutierrez HR, Pan L, Dickey EC, Eklund PC (2004) Debundling and dissolution of single-walled carbon nanotubes in amide solvents. J Am Chem Soc 126:6095–6105

    Article  CAS  Google Scholar 

  • Girifalco LA, Hodak M, Lee RS (2000) Carbon nanotubes, buckyballs, ropes, and a universal graphitic potential. Phys Rev B 62:13104–13110

    Article  CAS  Google Scholar 

  • He J-L, Yang Y, Yang X, Liu Y-L, Liu Z-H, Shen G-L, Yu R-Q (2006) β-Cyclodextrin incorporated carbon nanotube-modified electrode as an electrochemical sensor for rutin. Sens Actuator B Chem 114:94–100

    Article  CAS  Google Scholar 

  • Honigsbaum M (2001) The fever trail: the hunt for the cure for malaria. Macmillan, London

    Google Scholar 

  • Ikeda A, Hayashi K, Konishi T, Kikuchi J (2004) Solubilization and debundling of purified single-walled carbon nanotubes using solubilizing agents in an aqueous solution by high-speed vibration milling technique. Chem Commun 1334–1335

  • Karim MR, Lee CJ, Lee MS (2006) Synthesis and characterization of conducting polythiophene/carbon nanotubes composites. J Polym Sci Pol Chem 44:5283–5290

    Article  CAS  Google Scholar 

  • Kuhlmann O, Hofmann H, Muller SP, Weiss M (2003) Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin. Anticancer Drugs 14:411–416

    Article  CAS  Google Scholar 

  • Li H-M, Cheng F-Y, Duft AM, Adronov A (2005) Functionalization of single-walled carbon nanotubes with well-defined polystyrene by ‘click’ coupling. J Am Chem Soc 127:14518–14524

    Article  CAS  Google Scholar 

  • Liu Y, Li L, Zhang H-Y, Fan Z, Guan X-D (2003) Selective binding of chiral molecules of cinchona alkaloid by β- and γ-cyclodextrins and organoselenium-bridged bis(β-cyclodextrin)s. Bioorganic Chem 31:11–23

    Article  CAS  Google Scholar 

  • Liu Y, Chen G-S, Chen Y, Lin J (2005) Inclusion complexes of azadirachtin with native and methylated cyclodextrins: solubilization and binding ability. Bioorg Med Chem 13:4037–4042

    Article  CAS  Google Scholar 

  • Liu Z, Cai W, He L, Nakayama N, Chen K, Sun X, Chen X, Dai H (2007) In vivo biodistribution and highly efficient tumour targeting of carbon nanotubes in mice. Nat Nanotechnol 2:47–52

    Article  CAS  Google Scholar 

  • Lu X, Chen Z-F (2005) Curved pi-conjugation, aromaticity, and the related chemistry of small fullerenes (<C60) and single-walled carbon nanotubes. Chem Rev 105:3643–3696

    Article  CAS  Google Scholar 

  • Muderawan IW, Ong T-T, Lee T-C, Young DJ, Ching C-B, Ng S-C (2005) A reliable synthesis of 2- and 6-amino-β-cyclodextrin and permethylated-β-cyclodextrin. Tetrahedron Lett 46:7905–7907

    Article  CAS  Google Scholar 

  • Na N, Hu Y-P, Ouyang J, Baeyens WRG, Delanghe JR, Taes YEC, Xie M-X, Chen H-Y, Yang Y-P (2006) On the use of dispersed nanoparticles modified with single layer β-cyclodextrin as chiral selector to enhance enantioseparation of clenbuterol with capillary electrophoresis. Talanta 69:866–872

    Article  CAS  Google Scholar 

  • Ogoshi T, Takashima Y, Yamaguchi H, Harada A (2007) Chemically-responsive sol-gel transition of supramolecular single-walled carbon nanotubes (SWNTs) hydrogel made by hybrids of SWNTs and cyclodextrins. J Am Chem Soc 129:4878–4879

    Article  CAS  Google Scholar 

  • Sayes CM, Liang F, Hudson JL, Mendez J, Guo W-H, Beach JM, Moore VC, Doyle CD, West JL, Billups WE, Ausman KD, Colvin VL (2006) Functionalization density dependence of single-walled carbon nanotubes cytotoxicity in vitro. Toxicol Lett 161:135–142

    Article  CAS  Google Scholar 

  • Shi J, Wang Z, Li H-L (2006) Selfassembly of gold nanoparticles onto the surface of multiwall carbon nanotubes functionalized with mercaptobenzene moieties. J Nanopart Res 8:743–747

    Article  CAS  Google Scholar 

  • Strano MS, Dyke CA, Usrey ML, Barone PW, Allen MJ, Shan H-W, Kittrell C, Hauge RH, Tour JM, Smalley RE (2003) Electronic structure control of single-walled carbon nanotube functionalization. Science 301:1519–1522

    Article  CAS  Google Scholar 

  • Tasis D, Tagmatarchis N, Bianco A, Prato M (2006) Chemistry of carbon nanotubes. Chem Rev 106:1105–1136

    Article  CAS  Google Scholar 

  • Wang Z, Chen Y (2007) Supramolecular hydrogels hybridized with single-walled carbon nanotubes. Macromolecules 40:3402–3407

    Article  CAS  Google Scholar 

  • Wang G-Y, Liu X-J, Yu B, Luo G-A (2004) Electrocatalytic response of norepinephrine at a β-cyclodextrin incorporated carbon nanotube modified electrode. J Electroanal Chem 567:227–231

    Article  CAS  Google Scholar 

  • Yang R-C, Yang X-Y, Zhang Z-H, Zhang Y, Wang S-J, Cai Z, Jia Y, Ma Y-F, Zheng C, Lu Y-H, Roden RBS, Chen Y-S (2006) Single-walled carbon nanotubes-mediated in vivo and in vitro delivery of siRNA into antigen-presenting cells. Gene Ther 13:1714–1723

    Article  CAS  Google Scholar 

  • Zeng L, Zhang L, Barron AR (2005) Tailoring aqueous solubility of functionalized single-wall carbon nanotubes over a wide pH range through substituent chain length. Nano Lett 5:2001–2004

    Article  CAS  Google Scholar 

  • Zhang Z-H, Yang X-Y, Zhang Y, Zeng B, Wang S-J, Zhu T-H, Roden RBS, Chen Y-S, Yang R-C (2006) Delivery of telomerase reverse transcriptase small interfering RNA in complex with positively charged single-walled carbon nanotubes suppresses tumor growth. Clin Cancer Res 12:4933–4939

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work is supported by the ‘973’ Program (2006CB932900, 2006CB932700) from MoST and the Natural Science Foundation of China (20572048, 20421202, 20644004).

Author information

Authors and Affiliations

  1. State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China

    Zhen Guo, Li Liang, Dong-Mei Ren & Jian-Yu Zheng

  2. Center for Nanoscale Science and Technology and Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, China

    Jia-Jie Liang, Yan-Feng Ma, Xiao-Ying Yang & Yong-Sheng Chen

Authors
  1. Zhen Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Li Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jia-Jie Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yan-Feng Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiao-Ying Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Dong-Mei Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yong-Sheng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jian-Yu Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jian-Yu Zheng.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guo, Z., Liang, L., Liang, JJ. et al. Covalently β-cyclodextrin modified single-walled carbon nanotubes: a novel artificial receptor synthesized by ‘click’ chemistry. J Nanopart Res 10, 1077–1083 (2008). https://doi.org/10.1007/s11051-007-9338-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11051-007-9338-z

Keywords

Search

Navigation