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

    Year: 2014

    Journal: Cellulose, September 2014, 20141015

    Authors: Lokanathan R. Arcot (1), Meri Lundahl (1), Orlando J. Rojas (1)(2), Janne Laine (1)

    Last authors: Janne Laine

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

    Country: USA, United States of America, Finland

    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.