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The fluorescent 3-methylene-2,3-dihydroselenophene derivative (Φ(F) = 0.86 in CH(2)Cl(2)) incorporated in a dibenzobarrelene skeleton was synthesized by the reaction of a four-membered selenaplatinacycle with dimethyl acetylenedicarboxylate (DMAD) or reaction of bis(dibenzobarrelenyl) diselenide with DMAD in the presence of Pd(PPh(3))(4) and PPh(3). A fluorescent sulfur homologue (Φ(F) = 1.0 in CH(2)Cl(2)) was also synthesized by the reaction of bis(dibenzobarrelenyl) disulfide with DMAD in the presence of Pd(PPh(3))(4). Selected chemical transformations of these diesters were also investigated.

Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton