Nano Research

, Volume 3, Issue 11, pp 764–778 | Cite as

Improved non-covalent biofunctionalization of multi-walled carbon nanotubes using carbohydrate amphiphiles with a butterfly-like polyaromatic tail

  • Mohyeddin Assali
  • Manuel Pernía Leal
  • Inmaculada Fernández
  • Pablo Romero-Gomez
  • Rachid Baati
  • Noureddine KhiarEmail author
Open Access
Research Article


We have developed an efficient strategy for the non-covalent functionalization of multi-walled carbon nanotubes (MWCNTs) which allows a biomimetic presentation of carbohydrates on their surface by π-π stacking interactions. The strategy is based on the use of sugar-based amphiphiles functionalized with tetrabenzo[a,c,g,i]fluorene (Tbf), a polyaromatic compound with a topology that resembles a butterfly with open wings. The new carbohydrate-tethered Tbf amphiphiles have been synthesized in a straightforward manner using click chemistry. The reported method has been developed in order to improve the rather low ability of pyrene-based systems to exfoliate MWCNTs in water. By means of thermogravimetric analysis (TGA), ultraviolet (UV), infrared (IR), and fluorescence spectroscopies the interaction between MWCNTs and the Tbf group has been found to be stronger than those involving pyrene-based amphiphilic carbohydrates. The resulting aggregates with a multivalent sugar exposition on their surface are able to engage in specific ligand-lectin interactions similar to glycoconjugates on a cell membrane.


Carbon nanotubes non-covalent functionalization tetrabenzo[a,c,g,i]fluorene carbohydrates click chemistry biocompatible system 

Supplementary material

12274_2010_44_MOESM1_ESM.pdf (777 kb)
Supplementary material, approximately 605 KB.


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Copyright information

© Tsinghua University Press and Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Mohyeddin Assali
    • 1
  • Manuel Pernía Leal
  • Inmaculada Fernández
    • 2
  • Pablo Romero-Gomez
    • 3
  • Rachid Baati
    • 4
  • Noureddine Khiar
    • 1
    Email author
  1. 1.Instituto de Investigaciones QuímicasC.S.I.C-Universidad de SevillaSevillaSpain
  2. 2.Departamento de Química Orgánica y Farmacéutica, Facultad de FarmaciaUniversidad de SevillaSevillaSpain
  3. 3.Instituto de Ciencias de Materiales de SevillaC.S.I.C-Universidad de SevillaSevillaSpain
  4. 4.Laboratoire des Systèmes Chimiques Fonctionnels BP 60024Université de Strasbourg Faculté de Pharmacie CNRS/UMR 7199IllkirchFrance

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