Synthesis and axial electropolymerization of novel amino-derived silicon phthalocyanine-based organic semiconductors

Silicon phthalocyanines (SiPcs) are a class of molecules that have garnered large amounts of interest in the past decades, notably in the field of organic electronics. Their high level of conjugation allows them to promote charge transfer in an easy and efficient manner, in addition to holding high thermal and chemical stability. Herein, the synthesis of five novel amino-derived silicon phthalocyanines is reported, where the monomers are probed for in situ electropolymerization onto ITO conductive glass. Conductive films are obtained for the para- and ortho-bis(aminophenoxy) SiPc derivatives. The other three monomeric derivatives, however, did not yield any electropolymerized films. The polymerization is catalyzed by oxidation of the amino groups, introducing a phenazine bridge between the axial positions of the SiPcs. The electropolymerization is performed using cyclic voltammetry and further investigated through optical and spectroelectronic spectroscopy.