Electrochemistry and Electrogenerated Chemiluminescence of 1,3,5-Tri(anthracen-10-yl)-benzene-Centered Starburst Oligofluorenes.

Abstract

The electrochemistry and electrogenerated chemiluminescence (ECL) of three 1,3,5-tri(anthracen-10-yl)-benzene-centered starburst oligofluorenes (T1-T3) are reported in this paper. The compounds T1-T3 contain 1,3,5-tri(anthracen-10-yl)-benzene as a core with fluorene as an arm from monofluorene to trifluorene groups (n = 1-3), generating a rigid three-dimensional structure. The electrochemical behaviors of these compounds are likely to be tuned by the fluorene arms. In cyclic voltammograms, both the oxidation and reduction of T1 and T2 are characterized by three reversible one-electron transfers from the core while the oxidation and reduction of T3 are characterized by six reversible one-electron transfers from the core and the arms in acetonitrile:benzene (v:v = 1:1) solvent. The second oxidation and reduction waves of T1 show three reversible one-electron transfers from three fluorene arms, while the second and third oxidation and reduction waves of T2 and T3 exhibit three reversible one-electron transfers from the six fluorene arms. The multiple electron transfers in one molecule are confirmed by chronoamperometry at an ultramicroelectrode, simulations and DFT calculations. The T1-T3 compounds display strong absorption in UV-vis and blue fluorescence emission. Strong blue ECL emissions can be generated from T1, T2 and T3 under ion annihilation condition, which is assigned as S-route.