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.

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click chemistry, elemental analysis, functionalization of polymers, polystyrene

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