Science and Technology of Energetic Materials

Vol.77, No.4 (2016)

Research paper

Synthesis of novel polymeric energy materials with high nitrogen content by double click functionalization
Tsuyoshi Michinobu and Yoko Yoshitake


A novel approach to produce polymeric energy materials with high nitrogen contents is described. Electron-rich alkynes in the polymer side chain are sequentially functionalized by two different click reactions. A [2+2] cycloadditionretroelectrocyclization with tetracyanoethylene (TCNE) proceeds at room temperature without any side reactions yielding the 1,1,4,4-tetracyanobutadiene (TCBD) unit. This transformation efficiently increases the nitrogen content of the resulting polymer. The cyano groups of the TCBD unit are subjected to the cyano-azide cycloaddition reaction in the presence of zinc chloride (ZnCl2) or silver trifluoromethanesulfonate (AgOTf). The successful formation of tetrazole products is suggested from elemental analyses and thermal analysis.


click chemistry, elemental analysis, functionalization of polymers, polystyrene

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