Related Experiment Video
Updated: Sep 2, 2026

Visualizing Lignification Dynamics in Plants with Click Chemistry: Dual Labeling is BLISS!
Published on: January 26, 2018
Transformative Masked Ortho-Quinone Chemistry: From Direct Guaiacol Activation to Lignin-Based Adhesives
Dominik P Hoch1, Keven Walter1, Oliver Sipura1
1Humboldt-Universität zu Berlin, Department of Chemistry, Berlin, Germany.
Abstract:
Guaiacol moieties (1-hydroxy-2-methoxy-benzenes) are among the most abundant structural motifs in renewable biophenolic feedstocks, representing a potential industrial-scale stream from softwood lignin through biorefinery valorization. Here, the transformative chemistry of masked ortho-quinones (MoQs) is introduced, yielding reactive guaiacol derivatives to enable thiol-guaiacol connectivity (TGC) polymers. Phenyliodine(III)diacetate (PIDA) oxidizes guaiacols to chemically pure MoQs within minutes at room temperature, generating activated triguaiacol monomers that undergo thiol-MoQ Michael-type polyaddition with multithiols. This bulk polymerization leads to TGC-adhesives, reaching professional performance lap-shear strengths up to 16.9 ± 0.9 MPa. The robust strategy is extended to directly activate technical lignin, generating curable multi-MoQ prepolymers which bond aluminum with lap-shear strengths of 9.1 ± 0.7 MPa, positioning MoQs as a sustainable platform chemistry to bridge from lignin to high-performance materials.
More Related Videos
Related Concept Videos
Radical Chain-Growth Polymerization: Overview
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Cycloaddition Reactions: MO Requirements for Photochemical Activation

