One-pot synthesis of conjugated triphenylamine macrocycles and their complexation with fullerenes

Abstract

Triphenylamine derivates have been utilized as building blocks in hole-transporting materials. Herein, we describe the synthesis of three octyl-derived conjugated triphenylamine macrocycles with different sizes, and a 4-(2-ethylhexyloxy)-substituted cyclic triphenylamine hexamer using a palladium-catalyzed C–N coupling reaction. These conjugated triphenylamine macrocycles not only have interesting structures, but also are capable of complexing with C₆₀, C₇₀ and PC₆₁BM. Their binding stoichiometries with fullerenes were all determined to be 1 : 1 by an emission titration method. The association constants of these complexes were measured to be in the range of 0.115–1.53 × 10⁵ M⁻¹ depending on the cavity size of the triphenylamine macrocycles and the volume of the fullerenes. The space-charge-limited current properties of the complexes were further investigated using the fabricated ITO/PEDOT:PSS/active layer/Au devices.