Efficient blue emission from siloles

2,3,4,5-Tetraphenylsiloles with different 1,1-substituents on the ring silicon atoms, i.e., 1,1-dimethyl- 2,3,4,5-tetraphenylsilole (1), 1-methyl-1-(3-chloropropyl)-2,3,4,5-tetraphenylsilole (2), 1-methyl-1,2,3,4,5-pentaphenylsilole (3) and hexaphenylsilole (4), are synthesized and characterized. While all the siloles emit intense blue light readily observable by naked eyes under normal room illumination conditions, the film of their acyclic cousin without silicon, namely 1,2,3,4-tetraphenylbutadiene (5), does not fluoresce, revealing the vital role of the planar and rigid silacyclopentadiene ring in the solid-state photoluminescence process. The electronic transitions of the siloles can be tuned by varying the 1,1-substituents, and the inductive and conjugating effects of the aromatic rings confer low LUMO energy levels and high emission efficiencies on the phenyl-substituted siloles. The electroluminescence device of the 1-phenylsilole 3 shows a high brightness (4538 cd m(-2) at 18 V) and an excellent external quantum efficiency (0.65% at 17 V and 94 mA cm(-2)).