Thioether linked meso functionalized BODIPY DYEmer

Thioether linked meso BODIPY DYEmer 3 was synthesized by two different routes. The reaction of dipyrrothioketone 1 and 8-chloro BODIPY 2 in the presence of triethylamine followed by complexation with BF[Formula: see text] resulted in thioether linked meso functionalized BODIPY DYEmer 3. Using another route, the reaction of 8-chloro BODIPY 2 with sodium hydrosulphide (NaSH) at room temperature resulted in the thioether linked meso BODIPY DYEmer 3. The DYEmer 3 was characterized by 1 H, [Formula: see text]C, [Formula: see text]B, [Formula: see text]F NMR, HRMS, and single crystal X-ray crystallography. The properties of DYEmer 3 was compared with the previously reported thioether linked [Formula: see text] and [Formula: see text] BODIPY DYEmers 4 and 5. The structural parameters indicating the intramolecular arrangements of two BODIPY units of DYEmer were compared and corelated with the observed properties. The time-dependent DFT (TD-DFT) calculations suggested that the thioether group at meso position of BODIPY 3 stabilizes the LUMO energy than 8-chloro BODIPY 2. Compared to 8-chloro BODIPY 2 the HOMO-1 of DYEmer 3 is destabilized whereas the LUMO+1 is stabilized.