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Metal-free visible-light-induced dithiol–ene clicking via carbon nitride to valorize 4-pentenoic acid as a functional monomer

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Kumru,  Baris
Bernhard Schmidt, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

Mendoza Mesa,  Jose
Majd Al-Naji, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Antonietti,  Markus
Markus Antonietti, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Al-Naji,  Majd
Majd Al-Naji, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Kumru, B., Mendoza Mesa, J., Antonietti, M., & Al-Naji, M. (2019). Metal-free visible-light-induced dithiol–ene clicking via carbon nitride to valorize 4-pentenoic acid as a functional monomer. ACS Sustainable Chemistry & Engineering, 7(21), 17574-17579. doi:10.1021/acssuschemeng.9b05351.


Cite as: https://hdl.handle.net/21.11116/0000-0004-E674-6
Abstract
The necessity for more bio-based building blocks and processes have led to utilizing new polymerization approaches with a lower carbon footprint. Here, we demonstrate the synthesis of a visible-light-induced dithiol–ene clicking reaction between lignocellulosic biomass-derivable 4-pentenoic acid (4-PEA) and different dithiols, i.e., 1,2-ethanedithiol (EDT), 2,2-(ethylenedioxy)diethanethiol (EDDT), and 1,4-benzenedimethanethiol (BDT), using graphitic carbon nitride (g-CN) as a metal-free photocatalyst. The formation of dicarboxylic acid functional monomers were confirmed using 1H NMR and FT-IR. Furthermore, polyamides were synthesized from the dicarboxylic acid functional monomers to demonstrate the applicability of the monomers yielding new polyamide end polymers.