Multicomponent Coupling Approach to Cross-Conjugated Polymers from Vanillin-Based Monomers

2016/10/24 by Laure V. Kayser, Elizabeth M. Hartigan, Bruce A. Arndtsen · 1 citation
Biochemistry, Genetics and Molecular Biology · Chemistry · Engineering · #Biochemical and biochemical processes #Catalysis for Biomass Conversion #Synthesis of Indole Derivatives

paper · doi:10.1021/acssuschemeng.6b02302

openalex publication_date 2016/10/24 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/16

Abstract

We describe the use of vanillin-based monomers as a renewable feedstock for the synthesis of cross-conjugated polymers. This transformation exploits a catechyl-substituted phosphonite mediated multicomponent polymerization to convert vanillin-derived diimines, commercial diacid chlorides, and simple alkynes or alkenes into conjugated pyrrole-based polymers. The flexibility of the multicomponent polymerization has allowed for the efficient formation of families of vanillin-derived fluorescent polymers with tunable properties. This includes coupling vanillin with furan-based acid chlorides as the first cross-conjugated polymer composed of both components of lignocellulosic biomass.

Citations

• Modular Mesoionics: Understanding and Controlling Regioselectivity in 1,3-Dipolar Cycloadditions of Münchnone Derivatives
• Phospha-Münchnones: Electronic Structures and 1,3-Dipolar Cycloadditions
• Multicomponent Synthesis of Substituted and Fused-Ring Imidazoles via Phospha-münchnone Cycloaddition
• Metal-Free, Multicomponent Synthesis of Pyrrole-Based π-Conjugated Polymers from Imines, Acid Chlorides, and Alkynes
• Handbook of Conducting Polymers, 2 Volume Set

Cited by

• Montréalone [wikipedia]