A cascade-type anionic double cyclization of (o-silylphenyl)(o-halophenyl)acetylenes via lithiation followed by treatment with elemental chalcogen produces silicon and chalcogen-bridged stilbenes. Based on this reaction, a series of silicon and sulfur- or silicon and selenium-bridged ladder distyrylbenzenes have been synthesized. Their chemical modification by oxidation, crystal structures, and photophysical properties are described.
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