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Asymmetric cellulose nanocrystals: thiolation of reducing end groups via NHS–EDC coupling

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Abstract

Cellulose nanocrystals (CNC) were functionalized in aqueous media at the reducing, aldehyde ends of cellulose. CNC oxidation to produce carboxyl groups was followed by carbodiimide-mediated reaction to install thiol groups. The selectivity and extent of thiolation at the reducing ends was qualitatively confirmed by imaging (transmission electron microscopy) silver nanoparticles that tagged the CNC termini and by X-ray photoelectron spectroscopy, respectively. The adsorption of thiolated CNC onto gold surfaces as well as the viscoelastic property of the formed adlayer was investigated by using quartz crystal microgravimetry. The thiolated CNC chemisorbed on the surfaces were further analyzed for surface density and distribution by using atomic force microscopy. Overall we introduce a facile, mild asymmetric thiolation procedure as an efficient alternative to conventional reductive amination.

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Acknowledgments

The TEM images presented in this work were recorded at the Aalto University Nanomicroscopy Center (Aalto-NMC) premises. This work was partly supported by the Academy of Finland through its Centres of Excellence Programme (2014–2019) and under Project 132723612 HYBER.

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Authors and Affiliations

  1. Department of Forest Products Technology, School of Science and Technology, Aalto University School of Chemical Technology, Vuorimiehentie 1, P.O. Box 16100, 00076, Espoo, Finland

    Lokanathan R. Arcot, Meri Lundahl, Orlando J. Rojas & Janne Laine

  2. Departments of Forest Biomaterials and Chemical and Biomolecular Engineering, North Carolina State University, Raleigh, NC, 27695, USA

    Orlando J. Rojas

Authors
  1. Lokanathan R. Arcot
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  2. Meri Lundahl
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  3. Orlando J. Rojas
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  4. Janne Laine
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Corresponding authors

Correspondence to Lokanathan R. Arcot or Orlando J. Rojas.

Additional information

Lokanathan R. Arcot and Meri Lundahl have contributed equally to this work.

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Arcot, L.R., Lundahl, M., Rojas, O.J. et al. Asymmetric cellulose nanocrystals: thiolation of reducing end groups via NHS–EDC coupling. Cellulose 21, 4209–4218 (2014). https://doi.org/10.1007/s10570-014-0426-9

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  • DOI: https://doi.org/10.1007/s10570-014-0426-9

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