Conjugated Donor-Acceptor Macrocycles: Synthesis and Oxidation of ortho-Phenylene Bridged Cyclic Tetra(benzo[c][1,2,5]thiadiazole).

Here, we reported the synthesis of an ortho-phenylene bridged cyclic tetra(benzo[c][1,2,5]thiadiazole) (3) by stepwise Suzuki-Miyaura couplings. Subsequent oxidation of 3 yielded a two-sided fused product 4, identified as an ortho-phenylene bridged cyclic triphenyleno[1,2-c:7,8-c']bis([1,2,5]thiadiazole) dimer. The structures of 3 and 4 were confirmed by high-resolution mass spectroscopies (HRMS) and NMR techniques. Their photophysical and electrochemical properties were fully characterized by ultraviolet-visible (UV-vis), fluorescence spectroscopy, cyclic voltammetry, and density functional theory (DFT) calculations.