Preparation,Structure,and Properties of Tris(trimethylsilyl)silyl-substituted Anthracenes: Realization of Ideal Conformation for sigma-pi Conjugation Involving Eclipse of Si-Si sigma-Bond with p-Orbital of Aromatic Ring

摘要

Synthesis and X-ray diffraction analysis of 9-and 9,10-tris(trimethylsilyl)silyl(TTMSS)-substituted anthracenes were carried out to disclose that one of the Si-Si sigma-bonds in the TTMSS-substituted anthracenes were perpendicular to the aromatic rings.The introduction of the TTMSS groups induced red shift of UV absorption and fluorescence emission maxima as compared with the parent and 9-pentamethyldisilanylated anthracenes.Theoretical calculation suggests LUMO levels of the TTMSS-substituted anthracenes are lowered by sigma*-pi* orbital interaction.