N-Aryl stilbazolium dyes as sensitizers for solar cells

Octavia A Blackburn, Benjamin J Coe, Valentine Hahn, Madeleine Helliwell, James Raftery, Yien T Ta, Laurence M Peter, Hongxia Wang, Juan A Anta, Elena Guillen

Research output: Contribution to journalArticle

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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.
LanguageEnglish
Pages766-777
Number of pages12
JournalDyes and Pigments
Volume92
Issue number1
DOIs
StatusPublished - Jan 2012

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Charge transfer
Solar cells
Coloring Agents
Dyes
Salts
Chromophores
Acetonitrile
Nuclear magnetic resonance spectroscopy
Density functional theory
Mass spectrometry
Absorption spectra
Condensation
Infrared spectroscopy
Esters
Single crystals
Derivatives
X rays
Oxidation
Acids
Electrons

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Blackburn, O. A., Coe, B. J., Hahn, V., Helliwell, M., Raftery, J., Ta, Y. T., ... Guillen, E. (2012). N-Aryl stilbazolium dyes as sensitizers for solar cells. DOI: 10.1016/j.dyepig.2011.06.017

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; Guillen, Elena.

In: Dyes and Pigments, Vol. 92, No. 1, 01.2012, p. 766-777.

Research output: Contribution to journalArticle

Blackburn, OA, Coe, BJ, Hahn, V, Helliwell, M, Raftery, J, Ta, YT, Peter, LM, Wang, H, Anta, JA & Guillen, E 2012, 'N-Aryl stilbazolium dyes as sensitizers for solar cells' Dyes and Pigments, vol. 92, no. 1, pp. 766-777. DOI: 10.1016/j.dyepig.2011.06.017
Blackburn OA, Coe BJ, Hahn V, Helliwell M, Raftery J, Ta YT et al. N-Aryl stilbazolium dyes as sensitizers for solar cells. Dyes and Pigments. 2012 Jan;92(1):766-777. Available from, DOI: 10.1016/j.dyepig.2011.06.017
Blackburn, Octavia A ; Coe, Benjamin J ; Hahn, Valentine ; Helliwell, Madeleine ; Raftery, James ; Ta, Yien T ; Peter, Laurence M ; Wang, Hongxia ; Anta, Juan A ; Guillen, Elena. / N-Aryl stilbazolium dyes as sensitizers for solar cells. In: Dyes and Pigments. 2012 ; Vol. 92, No. 1. pp. 766-777
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