以C60、邻-硝基苯甲醛和甘氨酸为原料,经过1,3-偶极环加成反应得到2-(2-硝基苯基)吡咯烷[3′,4′∶1,2][60]富勒烯(NPF)。经紫外可见光谱、红外光谱、质谱、核磁共振谱等检测手段鉴定了NPF的结构。通过正交试验研究了反应物物质的量比、温度、时间和溶剂体积等对NPF产率的影响。结果表明,合成NPF的最佳工艺条件为:反应物物质的量比n(C60)∶n(邻-硝基苯甲醛)∶n(甘氨酸)为1∶4∶6,温度为80℃,反应时间为48h,溶剂甲苯体积为70mL,此时产率达81.2%(以消耗的C60计)。
A new nitrofulleropyrrolidine derivative 2-(2-nitrophenyl) fullerenopyrrolidine (NPF) was synthesized with [60] fullerene, glycine and o-nitrobenzaldehyde as primary materials by 1,3-dipolar cycloaddition reaction. Its structure was characterized by UV-Vis, FT-IR, ^1HNMR, ^13CNMR and MS. Effects of the ratios of raw materials, temperature, reaction time and the volume of toluene on the reaction were investigated by orthogonal method. The results show that the reaction conditions of synthesizing NPF with the yield of 81. 2% (based on consumed C60) are: molar ratio of C60, o-nitrobenzaldehyde and glycine 1 : 4 : 6, reaction temperature 80 ℃, reaction time 48h, volume of toluene solvent 70mL.