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

Here, we reported the synthesis of an <i>ortho</i>-phenylene bridged cyclic tetra(benzo[<i>c</i>][1,2,5]thiadiazole) (<b>3</b>) by stepwise Suzuki-Miyaura couplings. Subsequent oxidation of <b>3</b> yielded a two-sided fused product <b>4</b>, identified as an <i>ortho</i>-phenylene bridged cyclic triphenyleno[1,2-<i>c</i>:7,8-<i>c</i>']bis([1,2,5]thiadiazole) dimer. The structures of <b>3</b> and <b>4</b> 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.