Phthalocyanines (Pcs) are highly conjugated donor materials used in organic photovoltaic cells (OPVs). Previous work from our group demonstrated that a functionalized asymmetric phosphonic acid zinc Pc (PA-ZnPc) tethered to indium tin oxide (ITO) exhibited charge transfer rates at the ITO/organic interface that were dependent on the aggregation state of the chromophore as well as the in-plane and out-of-plane orientation with respect to the ITO surface. We hypothesized that the proliferation of subpopulations of chromophores (e.g. monomer and aggregate, in-plane and out-of-plane) in the monolayer were the result of the inhomogeneity of the relatively rough ITO surface. Self-assembled monolayers (SAMs) on Au, in contrast, are excellent systems for obtaining a fundamental understanding of chemical phenomena on surfaces and provide the opportunity to study the optimal orientation of asymmetric Pcs in a highly ordered surface. An asymmetric thiol zinc Pc (HS-ZnPc) has been synthesized to generate SAMs of Pcs on templated-stripped gold (TS-Au). These SAMs were characterized by electrochemistry and reflection absorption infrared spectroscopy (RAIRS) to reveal the order and orientation of the Pcs respect to the surface. Pcs SAMs will help understand the formation of different subpopulations on ITO which influences the charge transfer rates involved on the ITO/organic interface.

Synthesis of functionalized asymmetric thiol zinc phthalocyanine for fundamental studies of phthalocyanines behavior on gold

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.