Tunable SiN Hybrid Conjugated Materials

We report the synthesis of a family of N-aryl cyclosilazanes. The reaction of 1,2-bis­(trifluoro­methanesulfonate)­tetramethyl­disilane with para-substituted anilines gives six-membered rings with no observed condensation polymerization. X-ray crystallography reveals the cyclosilazane adopts a twist boat conformation with both nitrogens in a trigonal planar geometry. Solution phase UV–vis spectroscopic studies coupled with density functional theory calculations interrogate the ability of the nitrogen atom to bridge the σ- and π-conjugated moieties. Depending on the aromatic substituent, the cyclosilazane rings may be either more or less electron rich than an all silicon ring.