Biomimetic Dehydrogenation of Non‐Conventional Lignin Monomers on Cellulose Ferulate Interfaces

Author:

Elschner Thomas1ORCID,Geissler Andreas2,Adam Jörg3,Joseph Yvonne3,Fischer Steffen1

Affiliation:

1. Institute of Plant and Wood Chemistry Technische Universität Dresden Pienner Str. 19 01737 Tharandt Germany

2. Laboratory of Macromolecular and Paper Chemistry Technical University Darmstadt Peter‐Grünberg‐Str. 8 64287 Darmstadt Germany

3. Institute of Electronic and Sensor Materials TU Bergakademie Freiberg Gustav‐Zeuner‐Str. 3 09599 Freiberg Germany

Abstract

AbstractCellulose ferulate, synthesized by Mitsunobu reaction, is shaped into thin films and also used as an aqueous dispersion to perform artificial lignin polymerization on anchor groups. This biomimetic approach is carried out in a Quartz crystal microbalance with a dissipation monitoring (QCM‐D) device to enable online monitoring of the dehydrogenation, applying H2O2 and adsorbed horseradish peroxidase (HRP). The systematic use of phenylpropanoids with different oxidation states, i.e., ferulic acid, coniferyl aldehyde, coniferyl alcohol, and eugenol allowed to conclude structure‐property relationships. Both the deposited material, as well as the surface roughness increased with the hydrophobicity of the monomers. Beyond surface characterizations, py‐GC‐MS, HSQC NMR spectroscopy and Size exclusion chromatography (SEC) measurements revealed the linkage types β‐β, β‐5, 5‐5, and β‐O‐4, as well as the oligomeric character of the dehydrogenation products. All samples possessed an antibacterial activity against B. subtilis and can be used in the field of antimicrobial biomaterials.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Wiley

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