Cyclic Polymers from Alkynes: Synthesis, Scope, and Degradation

Parker T. Boeck, Rinku Yadav, Brent S. Sumerlin, Adam S. Veige

University of Florida

Reported in 2016, Roland's catalyst polymerizes alkynes to produce cyclic polyacetylenes and has led to a renaissance in cyclic polymer chemistry and the realization of their practical applications. Despite impending commercialization, a comprehensive scope study had yet to be performed with this catalyst and the functional group compatibility was unknown. Gratifyingly, we found Roland's catalyst successfully polymerized a wide variety of functional aliphatic and aromatic alkynes. Moreover, it was observed that the synthesized polyenes degraded rapidly simply upon dissolution in DMAc. A thorough understanding of the functional group tolerance of Roland's catalyst will inform future monomer design accelerating breakthroughs in cyclic polymer synthesis and the realization of their applications. Moreover, the degradation of these polymers now serves as a method for the synthesis of previously inaccessible linear polymers from their cyclic analogue.