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Methods development for the synthesis of 1,2,3-trithiolane monomers for a new platform of chemically recyclable polymers

Katherine Harry

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Presented at
ACS Fall 2022

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Abstract

With the rising demand and production of plastics in modern society, the current modes of disposal and recycling of these materials has resulted in an accumulation of plastic waste in landfills and the environment. Designing polymeric materials for a circular economy which possess intrinsic recyclability is a means to disrupt the current linear lifecycle of plastics and plastic waste pollution. In this work, we have developed a new platform of chemically recyclable polymers, (poly(trithiolanes)), which can be polymerized and depolymerized back to monomer using several methods. Key to the development of this new platform was the expansion of novel trithiolane monomers and sustainable methods for synthesizing them. In this work, green chemical practices were employed in the synthesis of trithiolane monomers using commercially available or bioderived starting materials and abundant petrochemical waste product, elemental sulfur. Building upon the previously reported synthetic approach, several new methods have been demonstrated to synthesize the trithiolane monomers. First, a solvent-free method for trithiolane monomer synthesis was established minimizing the need for expensive, harmful solvents and streamlining the purification of these monomers. Additionally, a novel method using near-visible wavelengths of light was developed to synthesize trithiolane monomers under mild conditions. Both light driven, solvent-free, and previously reported methods for the synthesis of trithiolane as monomers for a new platform of chemically recyclable polymers will be discussed.

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