Double-pillaring strategy for silacyclophanes: synthesis and structures of disilanyl double-pillared bisanthracenes
Waka Nakanishi1, Shunpei Hitosugi, Yusuke Shimada
1Department of Chemistry, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan.
Abstract:
A new series of silacyclophanes with two disilanyl pillars has been synthesized using a straightforward method. A silylation reaction of 1,8-dilithioanthracenes allowed the connection of two anthracene rings with two Si-Si bonds to afford disilanyl double-pillared bisanthracenes ((Si)DPBAs). The major product had an anti geometry of the anthracene rings, and a unique steplike structure favorable for σ-π conjugations was revealed by X-ray crystallographic analysis. Upon introducing a substituent at the 10-position of anthracene, we obtained a U-shaped isomer with syn geometry that yielded an excimer upon excitation and can decompose without steric protection.
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