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RAFT polymerization of styrene mediated by oxazolyl-functionalized trithiocarbonate RAFT agents

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Abstract

New oxazolyl benzhydryl and oxazolyl benzyl-functionalized trithiocarbonate RAFT agents, 1-(butylsulfanylthiocarbonylsulfanyl)-1-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-1-phenylmethane and 2-[4-((butylsulfanylthiocarbonylsulfanyl)methyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole, were prepared and employed as chain transfer agents in RAFT polymerization reactions. The RAFT polymerization of styrene, mediated by the appropriate oxazolyl-functionalized trithiocarbonate RAFT agent with AIBN as initiator at 70 °C, proceeded via controlled/living polymerization processes to produce the corresponding α-oxazolyl-functionalized polystyrene derivative, with the oxazolyl group introduced at the α-terminus of the polymer chain and the absence of any unfunctionalized polystyrene. Post-RAFT polymerization chain end modification of α-oxazolyl-functionalized polystyrene by acid-catalyzed hydrolysis reactions with dilute hydrochloric acid afforded the corresponding α-carboxyl-functionalized polystyrene derivative, with the retention of the butylsulfanylthiocarbonylsulfanyl moiety at the ω-terminus of the polymer chain. Polymer kinetic measurements show that each RAFT polymerization reaction follows first-order rate kinetics with respect to the percentage monomer consumption. The oxazolyl-functionalized benzhydryl fragmentation radical provides better control of the re-initiation of the polymerization of styrene than the oxazolyl-functionalized benzyl fragmentation radical. After consumption of the RAFT agent, the number average molecular weights of the functionalized polymers increases linearly with the percentage monomer conversion to produce α-oxazolyl-functionalized polystyrene derivatives with narrow molecular weight distributions.

Graphic abstract

New oxazolyl benzhydryl and oxazolyl benzyl-functionalized trithiocarbonate RAFT agents, 1-(butylsulfanylthiocarbonylsulfanyl)-1-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-1-phenylmethane and 2-[4-((butylsulfanylthiocarbonylsulfanyl)methyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole, were prepared and employed as chain transfer agents in RAFT polymerization reactions. The RAFT polymerization of styrene, mediated by 1-(butylsulfanylthiocarbonylsulfanyl)-1-[4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)phenyl]-1-phenylmethane or 2-[4-((butylsulfanylthiocarbonylsulfanyl)methyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole as chain transfer agents with AIBN as the initiator at 70 °C, proceeds via a controlled/living polymerization process to produce the corresponding α-oxazolyl-functionalized polystyrene derivative, with the oxazolyl group introduced at the α-terminus of the polymer chain.

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Acknowledgements

Financial assistance from the University of South Africa and the National Research Foundation, South Africa, is gratefully acknowledged. TS Motsoeneng would like to thank the National Research Foundation, South Africa, for financial assistance in the form as a Doctoral Scholarship.

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  1. Department of Chemistry, University of South Africa, PO Box 392, Pretoria, 0003, South Africa

    Gabriel J. Summers, Teboho S. Motsoeneng & Carol A. Summers

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Summers, G.J., Motsoeneng, T.S. & Summers, C.A. RAFT polymerization of styrene mediated by oxazolyl-functionalized trithiocarbonate RAFT agents. Polym. Bull. 78, 2251–2285 (2021). https://doi.org/10.1007/s00289-020-03211-6

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