Synthesis, photoluminescent and electrochemical properties of diacetoxyboron derivatives for bis-β-diketone linked thienothiophene

Abstract Six novel diacetoxyboron complexes of bis-β-diketones linked thienothiophene moiety were synthesized from acetoacetone by cyclization, Claisen condensation and chelation reaction. The obtained complexes were confirmed by means of 1 H NMR, FTIR, MS and elemental analysis and their electrochemical and photoluminescent properties were investigated by cyclic voltammetry, UV–vis absorption and fluorescence spectroscopy. The results showed that these diacetoxyboron complexes yielded a blue emission in DMF solution and emitted a greenish-yellow emission in powders and PMMA films. Especially, diacetoxyboron bis-β-diketonate with tert-butylphenyl thienothiophene exhibited the most intense photoluminescent intensity, highest quantum efficiency ( Φ u  = 0.95) in solution and longest lifetime value ( τ  = 38.42 μs) in PMMA film among these complexes. In addition, these diacetoxyboron complexes showed the low-lying LUMO energy levels (2.71–2.75 eV), which was suitable for electron transfer.