Distibylation of Acetylenes with Ph2Sb–SbPh2: Synthesis, Crystal Structures and Phosphorescence Properties of Bis(diphenylstibyl)ethenes

Abstract

Abstract Treatment of tetraphenyldistibine (1) with terminal arylacetylenes, XC6H5C≡CH (2a-c, X=H, F, OMe), gave the corresponding anti-addition products (E)-aryl-1,2-bis(diphenylstibyl)ethenes 3a-c in 11 - 17% yields. A similar reaction of 1 with 1,4-diphenylbutadiyne provided (E)-1,4-diphenyl- 1,2-bis(diphenylstibyl)but-1-en-3-yne (3d) in 28% yield. X-Ray diffraction studies on crystals of 3a, 3b and 3d revealed a congested configuration around the ethylene core. The optical properties of the adducts 3a-d were examined by measuring UV absorption and photoluminescence spectra. Interestingly, 3d showed phosphorescence in the solid state, which was enhanced at low temperature.