The reactions of [60]fullerene with benzyl chlorides and amino acids in chlorobenzene (PhCl) were investigated. Fulleropyrrolidines bearing ArCH moieties originating from the corresponding benzyl chlorides through C–Cl bond cleavage were obtained from these reactions. Use of PhCl/DMSO instead of PhCl as the solvent significantly improved the reaction efficiency. A detailed investigation of these reactions resulted in the discovery of other halides – such as allyl chloride, methallyl chloride, cinnamyl chloride, propargyl bromide, ethyl bromoacetate, bromoacetonitrile, bromomethane, bromopropane and bromobutane – that could also react with [60]fullerene and amino acids to produce fulleropyrrolidines. This reaction could be an alternative to the Prato reaction for synthesizing fulleropyrrolidines when aldehydes are expensive or unavailable from commercial sources. A plausible reaction mechanism for product formation involving C–X bond cleavage in the halide to form the aldehyde is proposed.

A series of energetic polymers, poly(vinyl p-nitrobenzal acetal)-g-polyglycidylazides (PVPNB-g-GAPs), are obtained via cross-linking reactions of poly(vinyl p-nitrobenzal acetal) (PVPNB) with four different molecular weights polyglycidylazides (GAPs) using toluene diisocyanate as cross-linking agent. The structures of the energetic polymers are characterized by ultraviolet visible spectra (UV-Vis), attenuated total reflectance-Fourier transform-infrared spectroscopy (ATR-FT-IR), 1 H nuclear magnetic resonance spectrometry ( 1 H NMR), and 13 C nuclear magnetic resonance spectrometry ( 13 C NMR). Differential scanning calorimetry (DSC) is applied to evaluate the glass-transition temperature of the polymers. DSC traces illustrate that PVPNB-g22 # GAP, PVPNB-g23 # GAP, and PVPNB-g24 # GAP have two distinct glass-transition temperatures, whereas PVPNB-g21 # GAP has one. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) are used to evaluate the thermal decomposition behavior of the four polymers and their compatibility with the main energetic components of TNT-based melt-cast explosives, such as cyclotetramethylene tetranitramine (HMX), cyclotrimethylene-trinitramine (RDX), triaminotrinitrobenzene (TATB), and 2,4,6-trinitrotoluene (TNT). The DTA and TGA curves obtained indicate that the polymers have excellent resistance to thermal decomposition up to 200 C. PVPNBg24 # GAP also exhibits good compatibility and could be safely used with TNT, HMX, and TATB but not with RDX.