Synthesis and electrochemical behaviour of [60]fullerene possessing poly(arylacetylene) dendrimer addends

61,61-Bis[4-{3,5-bis(3,5-di-tert-butylphenylethynyl)phenylethynyl}phenyl]-1 ,2-dihydro-1,2-methano[60]fullerene (10) and 61,61-bis[4-{3,5-bis[3,5-bis(3 ,5-di-tert-butylphenylethynyl)phenylethynyl]phenylethynyl}phenyl]-1,2-dihyd ro-1,2-methano[60]fullerene (11) with 1(st) and 2(nd) generation phenylacet ylene dendrimer addends were synthesised according to the Wudl method. Both monoadducts are obtained as single isomers in 18% and 23% yields, respecti vely. The structures of the products were established by FTIR, H-1 NMR, C-1 3 NMR and UV/VIS spectroscopy, as well as by mass spectrometry. All spectro scopic data confirm the exclusive formation of methano[60]fullerenes with [ 6,6]-closed structures. The electrochemical and spectroelectrochemical prop erties of 2(nd) generation dendrimer 7 and of its fullerene derivative 11 h ave been investigated. The cyclic voltammetric study shows that no signific ant interaction occurs in the ground state between the fullerene and the de ndrimer; the fullerene derivative retains the typical redox stability of 6, 6-closed derivatives in both the cyclic voltammetry (CV) and bulk electroly sis timescales.