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Green Synthesis of UV-Reactive Polycarbonates from Levoglucosenone And 5-Hydroxymethyl Furfural.

Aihemaiti KayishaerMattia AnnatelliChloe M HansomLouis M M MouterdeAurélien A M PeruFabio AricòFlorent AllaisSami Fadlallah
Published in: Macromolecular rapid communications (2023)
This study focuses on the synthesis of fully renewable polycarbonates (PCs) starting from cellulose-based platform molecules levoglucosenone (LGO) and 2,5-bis(hydroxymethyl)furan (BHMF). These unique bio-based PCs were obtained through the reaction of a citronellol-containing triol (Triol-citro) derived from LGO, with a dimethyl carbonate derivative of BHMF (BHMF-DC). Solvent-free polymerizations were targeted to minimize waste generation and promote an eco-friendly approach with a favorable environmental factor (E-factor). The choice of metal catalyst during polymerization significantly influenced the polymer properties, resulting in high molecular weight (up to 755 kDa) when Na 2 CO 3 was employed as inexpensive catalyst. Characterization using Nuclear Magnetic Resonance (NMR) confirmed the successful incorporation of the furan ring and the retention of the terminal double bond of citronellol pendant chain. Furthermore, under ultraviolet (UV) irradiation, the presence of both citronellol and furanic moieties induced singular structural changes, triggering the formation of three distinct structures within the polymer network, a phenomenon herein observed for the first time in this type of polymers. These findings pave the way to new functional materials prepared from renewable monomers with tunable properties. This article is protected by copyright. All rights reserved.
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