N-Aryl stilbazolium dyes as sensitizers for solar cells

Reference:

Blackburn, O. A., Coe, B. J., Hahn, V., Helliwell, M., Raftery, J., Ta, Y. T., Peter, L. M., Wang, H., Anta, J. A. and Guillen, E., 2012. N-Aryl stilbazolium dyes as sensitizers for solar cells. Dyes and Pigments, 92 (1), pp. 766-777.

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Official URL:

http://dx.doi.org/10.1016/j.dyepig.2011.06.017

Abstract

Eight new N-arylstilbazolium chromophores with electron donating -NR 2 (R = Me or Ph) substituents have been synthesized via Knoevenagel condensations and isolated as their PF6- salts. These compounds have been characterized by using various techniques including 1H NMR and IR spectroscopies and electrospray mass spectrometry. UV-vis absorption spectra recorded in acetonitrile are dominated by intense, low energy → (*) intramolecular charge-transfer (ICT) bands, and replacing Me with Ph increases the ICT energies. Cyclic voltammetric studies show irreversible reduction processes, together with oxidation waves that are irreversible for R = Me, but reversible for R = Ph. Single crystal X-ray structures have been determined for three of the methyl ester-substituted stilbazolium salts and for the Cl- salts of their picolinium precursors. Time-dependent density functional theory calculations afford reasonable predictions of ICT energies, but greater rigour is necessary for -NPh2 derivatives. The four new acid-functionalized dyes give moderate sensitization efficiencies (ca. 0.2%) when using TiO2-based photoanodes, with relatively higher values for R = Ph vs Me, while larger efficiencies (up to 0.8%) are achieved with ZnO substrates. 2011 Elsevier Ltd. All rights reserved.

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