Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Post-polymerization Modification of Polystyrene through Mn-Catalyzed Phosphorylation of Aromatic C(sp2)-H Bonds

Version 1 : Received: 15 May 2024 / Approved: 16 May 2024 / Online: 16 May 2024 (11:54:56 CEST)

A peer-reviewed article of this Preprint also exists.

Liu, R.; Lin, C.; Zou, Y.; Zhang, Y.; Sun, W.; Yang, Y.; Wei, C.; Zhong, J.; Shen, L. Post-Polymerization Modification of Polystyrene through Mn-Catalyzed Phosphorylation of Aromatic C(Sp2)–H Bonds. ACS Applied Polymer Materials 2024, 6, 11633–11640, doi:10.1021/acsapm.4c02382. Liu, R.; Lin, C.; Zou, Y.; Zhang, Y.; Sun, W.; Yang, Y.; Wei, C.; Zhong, J.; Shen, L. Post-Polymerization Modification of Polystyrene through Mn-Catalyzed Phosphorylation of Aromatic C(Sp2)–H Bonds. ACS Applied Polymer Materials 2024, 6, 11633–11640, doi:10.1021/acsapm.4c02382.

Abstract

The high flammability and lack of charrability of polystyrene (PS) pose significant limitations on its broader applications. Therefore, there is an urgent need for a straightforward and efficient method for the synthesis of flame-retardant PS, which still poses a considerable challenge. In this study, we present an efficient approach to enhance the flame-retardant properties of PS through direct phosphorylating aromatic C(sp2)-H bonds using commercially available and inexpensive manganese catalyst. A range of phosphonates served as reactive substrates to enable a tunable degree of polymer functionalization. The corresponding phosphorylated PS specimens were determined by means of 1H NMR, 31P NMR, FTIR spectroscopy and GPC. Microscale combustion calorimetry (MCC) tests indicate that this protocol indeed enhances the flame-retardant performance of PS. Moreover, other advantages associated with the incorporation of the phosphonate group have been observed, including improved thermal resistance and wettability. This cost-effective strategy of Mn-catalyzed C-H can also be utilized to directly obtain phosphonate modification of waste foamed PS and styrene acrylonitrile copolymer, providing a new method for the purpose of recycling and upgrading PS plastics.

Keywords

Post-Polymerization Modification; Mn-Catalyzed; Phosphorylation; Aromatic C(sp2)-H Bonds; Polystyrene

Subject

Chemistry and Materials Science, Materials Science and Technology

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