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

  • Gabriel J. SummersEmail author
  • Thembinkosi S. Mdletshe
  • Carol A. Summers
Original Paper


Three new naphthyl-functionalized trithiocarbonate RAFT agents, ethyl 1-naphthylmethyltrithiocarbonate, butyl 1-naphthylmethyltrithiocarbonate and dodecyl 1-naphthylmethyltrithiocarbonate, were prepared and employed as chain transfer agents in RAFT polymerization reactions. The RAFT polymerization of styrene, mediated by the different naphthyl-functionalized trithiocarbonate RAFT agents, with AIBN as the initiator at 75 °C proceeded via a controlled/living polymerization process to produce quantitative yields of α-naphthyl-functionalized polymers with the naphthyl group introduced at the α-terminus of the polymer chain. Ultraviolet visible spectroscopy and fluorescence spectroscopy data provide evidence for the incorporation of the naphthyl group at the α-terminus of the polymer chain. Polymer kinetic measurements show that each polymerization reaction follows first-order rate kinetics with respect to monomer consumption and the number average molecular weights increase linearly with monomer conversion to produce polymers with narrow molecular weight distributions. The percentage monomer conversion for each reaction was monitored by 1H NMR spectroscopy. The naphthyl-functionalized trithiocarbonate chain transfer agents and the α-naphthyl-functionalized polymers were characterized by 1H and 13C NMR spectroscopy, FTIR spectroscopy, size exclusion chromatography, ultraviolet visible spectroscopy and fluorescence spectroscopy.

Graphic abstract

The AIBN-initiated RAFT polymerization of styrene, mediated by new alkyl 1-naphthylmethyltrithiocarbonate RAFT agents at 75 °C proceeded via controlled/living polymerization processes to produce quantitative yields of α-naphthyl-functionalized polymers with the naphthyl group introduced at the α-terminus of the polymer chain.


RAFT polymerization Naphthyl-functionalized trithiocarbonate RAFT agents α-Naphthyl-functionalized polystyrene Fluorescence spectroscopy 



Funding from the University of South Africa and the National Research Foundation, South Africa, is gratefully acknowledged. TS Mdletshe would like to thank the National Research Foundation, South Africa, for financial assistance in the form of a doctoral scholarship.


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of South Africa (UNISA)PretoriaSouth Africa

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