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Facile synthesis of β-functionalized “push-pull” Zn(II) porphyrins for DSSC applications

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Abstract Three new β -substituted “push-pull” Zn(II) porphyrin dyes with various electron donors at meso- positions and cyanoacetic acid as acceptor at β -position have been designed and synthesized. These… Click to show full abstract

Abstract Three new β -substituted “push-pull” Zn(II) porphyrin dyes with various electron donors at meso- positions and cyanoacetic acid as acceptor at β -position have been designed and synthesized. These porphyrins have been characterized by UV-Vis, Fluorescence, 1 H NMR and 13 C NMR spectroscopic techniques and cyclic voltammetric studies. The Soret and Q band of Zn(II) porphyrin dyes were found to be red-shifted (30–35 nm) as compared to ZnTPP. The fluorescence quenching and the decrement in quantum yield and lifetime suggest intramolecular charge transfer from donor to acceptor. Zn porphyrins exhibited anodic shift in their first redox potentials (0.03–0.11 V) as compared to ZnTPP. The HOMO-LUMO energy levels of Zn porphyrin dyes were compared with the conduction band of TiO 2 and the electrolyte I − /I 3 − . The HOMO levels of all the dyes are sufficiently higher than the energy level of electrolyte I − /I 3 − and LUMO levels significantly lower than the conduction band of TiO 2 which reflect the feasibility of facile electron-transfer. ZnT(Mes)P(CN-COOH) has been co-sensitized with N719 dye to further improve the PCE efficiency. These dyes displayed power conversion efficiency (PCE) of η  = 1.72–3.13% where co-sensitized ZnT(Mes)P(CN-COOH) (N719) dye demonstrated maximum PCE efficiency up to 5.35%, with a J sc of 11.8 mA cm −2 , a V oc of 630 mV and a fill factor (FF) of 72% due to better light harvesting capacity.

Keywords: synthesis functionalized; facile synthesis; push; push pull; porphyrin dyes

Journal Title: Dyes and Pigments
Year Published: 2017

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