The Sonogashira cross-coupling reaction between 4-bromo-2, 1,3-benzothiadiazole, and the respective para-substituted phenylethynyl derivatives could synthesize the BTDs. In addition, the BTD-Ph is prepared by reacting 4-bromo-2,1,3-benzothiadiazole (Br-BTD)and palladium-MAI catalyst, and the dynamic phenylboronic acid reagent in the starting system or dynamic o-amino pyridine reagent[1-2].
[1] Pradhan, Asit Kumar et al. “Effects of donor and acceptor substituents on the photophysics of 4-ethynyl-2,1,3-benzothiadiazole derivatives?.” Physical Chemistry Chemical Physics 42 (2023): 29327–29340.
[2] AMARO DA SILVEIRA NETO B; CORREA J R; OLIVEIRA CARVALHO T; PIMENTA ROCHA CARVALHO P. "Selective cellular markers in selective cellular imaging of organelles such as mitochondria, nucleus and other organelles, are derived from 4-bromo-2,1,3-benzothiadiazole nucleus via homogeneous catalysis of palladium complex" BR102016025541(A2)