1,3-Dipolar cycloaddition polymerization reactions of novel macromolecules containing sym-tetrazine rings

We report the synthesis of sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine through 1,3-dipolar cycloaddition polymerization reactions where bis-hydrazonoyl chloride was converted to a tetrazine based polymer through bis-nitrilimine intermediates. Polymer molecular weights approached 90,000 g/mol under optimized reaction conditions with low polydispersity indices of approximately 1.05. The polymers are soluble in a variety of organic solvents and the reactions were characterized through a series of spectral, thermal and chromatographic techniques. The tetrazine based polymers display high complexation potential with cobalt chloride demonstrating metal complexation capability.