N-Aryl stilbazolium dyes as sensitizers for solar cells

Blackburn, Octavia A., Coe, Benjamin J., Hahn, Valentine, Helliwell, Madeleine, Raftery, James, Ta, Yien T., Peter, Laurence M., Wang, Hongxia, Anta, Juan A., & Guillén, Elena (2012) N-Aryl stilbazolium dyes as sensitizers for solar cells. Dyes and Pigments, 92(1), pp. 766-777.

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Eight new N-arylstilbazolium chromophores with electron donating –NR2 (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 π → π* 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.

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ID Code: 46442
Item Type: Journal Article
Refereed: Yes
Keywords: Stilbazolium salts; Dye sensitizers; Solar cells; UV-visible absorption spectroscopy; Electrochemistry; Density functional theory
DOI: 10.1016/j.dyepig.2011.06.017
ISSN: 01437208
Divisions: Past > QUT Faculties & Divisions > Faculty of Built Environment and Engineering
Copyright Owner: Copyright 2011 Elsevier Ltd.
Copyright Statement: NOTICE: this is the author’s version of a work that was accepted for publication in Dyes and Pigments. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Dyes and Pigments, [Volume 92, Issue 1, (January 2012)]. DOI: 10.1016/j.dyepig.2011.06.017
Deposited On: 12 Oct 2011 22:58
Last Modified: 12 Sep 2013 23:34

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