Electrochemical Characteristics of Water-Soluble Phosphate-Functionalized Naphthalene- and Perylene-Bisimides and Their Zirconium Bisphosphate Multilayers on ITO Electrode
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N,N’-bis(ethyldihydrogen phosphate)-1,4,5,8-naphthalene bis(dicarboximide) (EPNI) and N,N’-bis(ethyldihydrogen phosphate)-3,4,9,10-perylene bis(dicarboximide) (EPPI) and their zirconium bisphosphate multilayers (Zr-EPNI and Zr-EPPI), that had been briefly reported by us, were further investigated in terms of their electrochemical properties. EPNI in aqueous solution showed typical two reversible reductions at ITO electrode but the reductions were strongly dependent on solution pH while EPPI showed only an irreversible reduction. The single and mixed multilayers of Zr-EPNI and Zr-EPPI were well constructed on ITO electrode by the alternate adsorptions of zirconium ion and the bisimides. While Zr-EPNI multilayer on ITO electrode showed single broad reversible reduction with E1/2 = −0.68 V, Zr-EPPI gave two separated reductions at E1/2 = −0.54 and −0.81 V vs SCE, quite differently from the solution properties. The average layer densities of the multilayers were estimated as 1.5×10−10 and 2.3×10−10 mol/cm2 for Zr-EPNI and Zr-EPPI, respectively. Both the monolayers of Zr-EPNI and Zr-EPPI could not completely block the electron transfer between Fe(CN)6 3− in solution and ITO electrode but 3−5 layers of Zr-EPNI and Zr- EPPI could block it completely and mediated the one-way electron transfer at the potential shifted to their reduction potentials. When the monolayer of zirconium 1,10-decanediylbisphosphonate (Zr-DBP) was used as a sublayer of Zr-EPNI and Zr-EPPI layers, the mediated electron transfer became prominent without any direct electron transfer.
Abstract
N,N’-bis(ethyldihydrogen phosphate)-1,4,5,8-naphthalene bis(dicarboximide) (EPNI) and N,N’-bis(ethyldihydrogen phosphate)-3,4,9,10-perylene bis(dicarboximide) (EPPI) and their zirconium bisphosphate multilayers (Zr-EPNI and Zr-EPPI), that had been briefly reported by us, were further investigated in terms of their electrochemical properties. EPNI in aqueous solution showed typical two reversible reductions at ITO electrode but the reductions were strongly dependent on solution pH while EPPI showed only an irreversible reduction. The single and mixed multilayers of Zr-EPNI and Zr-EPPI were well constructed on ITO electrode by the alternate adsorptions of zirconium ion and the bisimides. While Zr-EPNI multilayer on ITO electrode showed single broad reversible reduction with E1/2 = −0.68 V, Zr-EPPI gave two separated reductions at E1/2 = −0.54 and −0.81 V vs SCE, quite differently from the solution properties. The average layer densities of the multilayers were estimated as 1.5×10−10 and 2.3×10−10 mol/cm2 for Zr-EPNI and Zr-EPPI, respectively. Both the monolayers of Zr-EPNI and Zr-EPPI could not completely block the electron transfer between Fe(CN)6 3− in solution and ITO electrode but 3−5 layers of Zr-EPNI and Zr- EPPI could block it completely and mediated the one-way electron transfer at the potential shifted to their reduction potentials. When the monolayer of zirconium 1,10-decanediylbisphosphonate (Zr-DBP) was used as a sublayer of Zr-EPNI and Zr-EPPI layers, the mediated electron transfer became prominent without any direct electron transfer.
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