Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives

摘要

Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsi-lylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (Φ_F) of 0.65. In contrast, the emission properties of a triphenylsilylpheny-l(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (Φ_F = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic vol-tammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.