CP 11

	Scheme 10 Synthesis of C60-PGN and C60-GAP.

It has been calculated that the enthalpy of formation of Cp-5 is 2782.2 kJ mol−1, while its detonation velocity and pressure are 3282 km s−1 and 4.443 GPa, respectively.112 Upon complete combustion, the total heat of combustion for Cp-5 is 2.17 × 105 kJ mol−1 due to its high carbon content. It seems that this compound may not be useful as the main ingredient of an explosive or a propellant but it might be a good additive for heat-generating energetic compositions. To improve the energetic content of fullerene derivatives, more nitro groups can be introduced on the fullerene skeleton. Such a strategy has been recently attempted, where a high-nitrogen-content derivative, C60(NO2)14 (FP, CP-10), was prepared and characterized,113 using a prolonged treatment of C60 in benzene with very high concentrations of N2O4. However, Cp-10 is not so thermally stable and it deflagrates when heated above 170 °C in nitrogen or air, releasing a considerable amount of heat. This compound may be used as a powerful explosive, depending on its sensitivity, which has not been reported. In addition to the nitro-derivatives of fullerene, fullerene nitrates have also been reported that can be used in propellant compositions as energetic burn rate modifiers. As a typical example, fullerene ethylenediamine nitrate (Cp-11, FEDN) was synthesized by reacting fullerene and ethylenediamine in diluted nitric acid (Scheme ).114

1. 112 B. Tan, R. Peng, H. Li, B. O. Jin, S. Chu and X. Long, Theoretical investigation of an energetic fullerene derivative, J. Comput. Chem., 2010, 31, 2233–2237 CAS.
2. 113 F. Cataldo, O. Ursini and G. Angelini, Synthesis and explosive decomposition of polynitro[60]fullerene, Carbon, 2013, 62, 413–421 CrossRef CAS.
3. 114 B.-L. Chen, B. Jin, R.-F. Peng, F.-Q. Zhao, J.-H. Yi, W.-J. Han, H.-J. Guan and S.-J. Chu, Synthesis and characterization of fullerene-ethylenediamine nitrate, Chin. J. Energet. Mater., 2014, 22, 186–191 CAS.

http://pubs.rsc.org/en/content/articlehtml/2016/nr/c5nr07855e

///////////