Synthesis and properties of spiro-type heterasumanenes containing group 14 elements as bridging atoms†

Abstract

Spiro-type heterasumanenes composed of two triphenylenodithiophene units and group 14 bridging atoms were synthesized by stepwise lithiations of hexaalkoxytriphenylene derivatives and treatment with heteroatom reagents. The molecular structures of the spirobiheterasumanenes, which contain orthogonal two p-frameworks, were determined by single-crystal X-ray diffraction analyses. The stepwise and reversible two-electron oxidation process revealed that the orthogonal p-frameworks interact with each other through spiro-conjugation in their oxidized state.