The Diels-Alder Reaction Of 2-(Piperidine-carbodithioate)-1, 3-Butadiene With C₆₀-fullerene

the Diels-Alder reaction of 2-(piperidine-carbodithioate)-l,3-Butadiene withCeo-fullerene.Organic functionalization of fullernene is fascinating and promising for new material chemistry because of its unique spherical structure and feasibility in bulk production. According to theoretical calculations,C60 exhibits a LUMO(t1u) comparatively low in energy. Consequently, C60 behaves like an electronegative molecule which reversibly accepts up to six electrons in solution. The Cyclic voltammetry and the electron affinity measured for C60 confirm that it is a moderate electron acceptor. Upon light excitation, C60 can form singlet because of absording energy, quickly transfers the triplet state with near unit efficiency.Addition reactions instead of substitution reactions are therefore typically undergone by Ceo molecule. Among these reactions, cycloaddition reactions are the most reliable methods, For example , cyclopropanation, [2+2] cycloaddition, [3+2] cycloaddition, [4+2] cycloaddition ,the Diels-Alder reaction being particularly successful. Addition reactions occurs on the [6/6] junction bonds between the two six-membered rings on C60 surface.Recently, multiple addition to C60 becomes of increasing interest.In principle, the bisaddition reaction can form eight different regioisomers:cis-l, cis-2, cis-3, e, trans-1, trans-2, trans-3,and trans-4. Usuallly, the bisadditions take place without sufficient regioselectivity and the separation chromatographic techniques.In this paper, we will introduce the Diels-Alder reaction of 2-(piperidine-carbodithioate)-1,3-Butadiene with C60-fullerene. Semi-empirical methods(AM1 and PM3) were carried out to calculate the electronic structure and front orbits of monoadduct and bisadducts. The stability of bisadducts were discussed by energies of heat of conformation.The result implies that the type e is the most stable one.