Thiophene-functionalized octupolar triindoles: Synthesis and photophysical properties

Two thiophene-functionalized octupolar triindole molecules were synthesized through Suzuki and Sonogashira cross-coupling reactions. Their photophysical and electrochemical properties were explored. The spectroscopic data demonstrate that triindole is an excellent rich electronic central donor for building octupolar optoelectronic molecules and possesses excellent luminescent properties. Thiophenylethynyl substituted triindole compound 3,8,13-tri(2-thiophenylethynyl)-5,10,15-tributyltriindole forms an intermolecular aggregation induced by pi-pi stacking from the rigid coplanar molecular scaffold. The redox curves and results of theoretical calculation imply that the two compounds have low ionization potential and low E-1/2 (oxd) which may be originated from the high electronic density of both triindole and thiophene groups. (C) 2012 Elsevier B.V. All rights reserved.