2-(2,5-二羟基苯基)-5-甲基-2,5-二氢吡咯并[3,4]富勒烯的合成和电子光谱的理论研究

Synthesis of [2-(2,5-Dihydroxyphenyl)-5-methyl-2,5-dihydropyrrolino]- [3,4]fullerene and Theoretical Studies on Its Electronic Spectra

利用丙氨酸和2,5-二羟基苯甲醛所形成的亚胺叶立德与C60发生1,3-偶极环加成反应,合成并分离、纯化制备了一种新的C60吡咯烷衍生物:2-(2-5-二羟基苯基)-5-甲基-2,5-二氢吡咯并[3,4]富勒烯.通过1HNMR,FT-IR,UV-vis和元素分析确定了其结构,研究了体系的电化学和荧光性质.采用密度泛函的方法,在B3LYP/6-31G水平上对分子的几何构型进行了优化,得到稳定的几何构型;运用INDO/S方法计算了化合物的电子光谱,计算结果434.2nm与实验值432.0nm基本一致.

A new compound [2-（2,5-dihydroxyphenyl）-5-methyl-2,5-dihydropyrrolino][3,4]fullerene was synthesized by the 1,3-dipolar cycloaddition reaction between the fullerene （C60） and azomethine ylide （prepared from 2-aminopropanoic acid and 2,5-dihydroxybenzal）, which was characterized by 1H NMR, FT-IR, UV-vis spectra and elemental analysis. Its properties of electrochemistry and fluorescence were also studied. The geometry configurations of the compound were optimized using the density functional theory at B3LYP/6-31G level. The electronic spectra of the compound were studied by INDO/S method. The comoutational result （434.2 nm） accorded with the experimental one （432.0 nm）.