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Z. Naturforsch. 2014,
69b, 1181 – 1187
doi:10.5560/ZNB.2014-4166
Distibylation of Acetylenes with Ph2Sb–SbPh2: Synthesis, Crystal Structures and Phosphorescence Properties of Bis(diphenylstibyl)ethenes
1 Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan
2 Division of Materials Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
3 Advanced Materials Research Labs, Sumitomo Chemical Co. Ltd., 6 Kitahara, Tsukuba 300-3294, Japan
Reprint requests to J. Ohshita. Fax: +81-82-424-5494. E-mail:
jo@hiroshima-u.ac.jp
Received July 31, 2014 / published online December 19, 2014
Dedicated to Professor Hubert Schmidbaur on the occasion of his 80th birthday
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.
Key words: Distibine, Distibylethene, Phosphorescence, Crystal Structure