Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC

C. Koenigsmann, T. S. Ripolles, B. J. Brennan, C. F A Negre, M. Koepf, A. C. Durrell, R. L. Milot, J. A. Torre, R. H. Crabtree, V. S. Batista, Gary W Brudvig, J. Bisquert, C. A. Schmuttenmaer

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

An efficient synthetic protocol to functionalize the cyanoacrylic acid anchoring group of commercially available MK-2 dye with a highly water-stable hydroxamate anchoring group is described. Extensive characterization of this hydroxamate-modified dye (MK-2HA) reveals that the modification does not affect its favorable optoelectronic properties. Dye-sensitized solar cells (DSSCs) prepared with the MK-2HA dye attain improved efficiency (6.9%), relative to analogously prepared devices with commercial MK-2 and N719 dyes. The hydroxamate anchoring group also contributes to significantly increased water stability, with a decrease in the rate constant for dye desorption of MK-2HA relative to MK-2 in the presence of water by as much as 37.5%. In addition, the hydroxamate-anchored dye undergoes essentially no loss in DSSC efficiency and the external quantum efficiency improves when up to 20% water is purposefully added to the electrolyte. In contrast, devices prepared with the commercial dye suffer a 50% decline in efficiency under identical conditions, with a concomitant decrease in external quantum efficiency. Collectively, our results indicate that covalent functionalization of organic dyes with hydroxamate anchoring groups is a simple and efficient approach to improving the water stability of the dye-semiconductor interface and overall device durability. This journal is

Original languageEnglish
Pages (from-to)16629-16641
Number of pages13
JournalPhysical Chemistry Chemical Physics
Volume16
Issue number31
DOIs
Publication statusPublished - Aug 21 2014

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Hydroxamic Acids
Anchors
Substitution reactions
Coloring Agents
solar cells
dyes
substitutes
acids
Water
water
Quantum efficiency
quantum efficiency
2-(2-(2-chloro-3-(2-(3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl)-vinyl)-cyclohex-2-enylidene)-ethylidene)-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid
Dye-sensitized solar cells
Optoelectronic devices
Electrolytes
Rate constants
Desorption
Durability
durability

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Physics and Astronomy(all)

Cite this

Koenigsmann, C., Ripolles, T. S., Brennan, B. J., Negre, C. F. A., Koepf, M., Durrell, A. C., ... Schmuttenmaer, C. A. (2014). Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC. Physical Chemistry Chemical Physics, 16(31), 16629-16641. https://doi.org/10.1039/c4cp02405b

Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC. / Koenigsmann, C.; Ripolles, T. S.; Brennan, B. J.; Negre, C. F A; Koepf, M.; Durrell, A. C.; Milot, R. L.; Torre, J. A.; Crabtree, R. H.; Batista, V. S.; Brudvig, Gary W; Bisquert, J.; Schmuttenmaer, C. A.

In: Physical Chemistry Chemical Physics, Vol. 16, No. 31, 21.08.2014, p. 16629-16641.

Research output: Contribution to journalArticle

Koenigsmann, C, Ripolles, TS, Brennan, BJ, Negre, CFA, Koepf, M, Durrell, AC, Milot, RL, Torre, JA, Crabtree, RH, Batista, VS, Brudvig, GW, Bisquert, J & Schmuttenmaer, CA 2014, 'Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC', Physical Chemistry Chemical Physics, vol. 16, no. 31, pp. 16629-16641. https://doi.org/10.1039/c4cp02405b
Koenigsmann, C. ; Ripolles, T. S. ; Brennan, B. J. ; Negre, C. F A ; Koepf, M. ; Durrell, A. C. ; Milot, R. L. ; Torre, J. A. ; Crabtree, R. H. ; Batista, V. S. ; Brudvig, Gary W ; Bisquert, J. ; Schmuttenmaer, C. A. / Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC. In: Physical Chemistry Chemical Physics. 2014 ; Vol. 16, No. 31. pp. 16629-16641.
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