Sulfur-containing polymer is promising to the application of the optical, anti-corrosion and antifouling materials. Using sulfur-containing C1 building blocks [i.e. carbonyl sulfide (COS), carbon disulfide (CS2)] to copolymerize with epoxides have been rapidly developed in our group and others. This talk reports two metal-free routes for the reaction of COS with epoxides.
1) The inhibition of oxygen-sulfur exchange reaction (O-S ER)1 for synthesizing poly(monothiocarbonate)s. Two types of organocatalysts will present, one is the combination of Lewis bases including amidine, guanidine, or quaternary onium salts with triethyl borane.2 A highly transparent and colorless poly(monothiocarbonate)s are obtained with > 99% tail-to-head content and high Mns of up to 92.5 kg/mol. O-S ER that would generate random thiocarbonate and carbonate units, were totally suppressed in most instances. The turnover frequency (TOF) of these Lewis pairs are as high as 240 h-1 at ambient temperature. The other is the combination of organic bases and thioureas via cooperative catalysis.3 Poly(monothiocarbonate)s are obtained with 100 % alternating degree, > 99% tail-to-head content, high Mns of up to 98.4 kg/mol and narrow molecular weight distributions (1.13-1.23). TOFs of the catalysts are up to 112 h−1 at 25 °C. 
2) The utilization of O-S ER for synthesizing poly(thioether)s using COS and epoxides as the starting materials.4 This route undergoes the coupling reaction of COS with epoxides, decarboxylative ring-opening polymerization (ROP) of the generated mixed cyclic thiocarbonates with releasing CO2(a little bit COS). And this method is also applied to the reaction of carbon disufide with epoxides, providing a new pathway to produce COS and poly(thioether)s simultaneously. 
Finally, we’ll present the transformation of poly(monothiocarbonate)s to poly(thioether)s by using O-S ER process, which is a polymer A to polymer B method for recycling the polymers.

Organocatalytic Synthesis of Sulfur-containing Polymers

**Session Chair: **Jason Lim, Li Zibiao 
	**Poster Judges: **Li Bofan and Wang Pei

SYM B - Re-cyclability and Re-manufacturing

technical paper

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MATERIALS FOR HUMANITY (MH 21)

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Xing-Hong Zhang

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Organocatalytic Synthesis of Sulfur-containing Polymers

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