Abstract
A new functionalized [60]fullerene-glycidyl azide polymer (C60-GAP) was synthesized for the first time using a modified Bingel reaction of [60]fullerene (C60) and bromomalonic acid glycidyl azide polymer ester (BM-GAP). The product was characterized by Fourier transform infrared (FTIR), ultraviolet-visible (UV-Vis), and nuclear magnetic resonance spectroscopy (NMR) analyses. Results confirmed the successful preparation of C60-GAP. Moreover, the thermal decomposition of C60-GAP was analyzed by differential scanning calorimetry (DSC), thermogravimetric analysis coupled with infrared spectroscopy (TGA-IR), and in situ FTIR. C60-GAP decomposition showed a three-step thermal process. The first step was due to the reaction of the azide group and fullerene at approximately 150 °C. The second step was ascribed to the remainder decomposition of the GAP main chain and N-heterocyclic at approximately 240 °C. The final step was attributed to the burning decomposition of amorphous carbon and carbon cage at around 600 °C.
Highlights
Fullerene has been extensively developed with remarkable achievement since Kratschmer et al first produced [60]fullerene (C60) on a preparative scale [1,2]
Considering glycidyl azide polymer (GAP) is an azide energetic material and can be modified through various reactions, GAP was grafted on C60 to afford energetic fullerene derivatives C60-PGN in three steps, as shown in Scheme 1
The second thermal degradation at about 200~400 °C is probably due to the decomposition of the GAP main chain and N-heterocyclic decomposition; and the last step is maybe because of the thermal decomposition of fullerene cage (Scheme 2)
Summary
Fullerene has been extensively developed with remarkable achievement since Kratschmer et al first produced [60]fullerene (C60) on a preparative scale [1,2]. C60 and its functionalized derivatives are important and can be remarkably applied in various studies because of their unique structure and physical properties [3,4,5]. If some energetic groups, such as the nitro group, would be added into C60, an enhanced fuel additive may be obtained [9]. The nitro group that directly bonds to fullerene reacts slowly with H2O to afford partially hydroxylated products poly(hydroxynitro)-fullerenes [13]. Achieving a stable energetic fullerene derivative remains a challenge
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