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

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 C(60), C(70) and PC(61)BM. 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 × 10(5) 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.