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 language | English |
|---|---|
| Pages (from-to) | 16629-16641 |
| Number of pages | 13 |
| Journal | Physical Chemistry Chemical Physics |
| Volume | 16 |
| Issue number | 31 |
| DOIs | |
| Publication status | Published - Aug 21 2014 |
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ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Physics and Astronomy(all)
Cite this
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 journal › Article
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TY - JOUR
T1 - Substitution of a hydroxamic acid anchor into the MK-2 dye for enhanced photovoltaic performance and water stability in a DSSC
AU - Koenigsmann, C.
AU - Ripolles, T. S.
AU - Brennan, B. J.
AU - Negre, C. F A
AU - Koepf, M.
AU - Durrell, A. C.
AU - Milot, R. L.
AU - Torre, J. A.
AU - Crabtree, R. H.
AU - Batista, V. S.
AU - Brudvig, Gary W
AU - Bisquert, J.
AU - Schmuttenmaer, C. A.
PY - 2014/8/21
Y1 - 2014/8/21
N2 - 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
AB - 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
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U2 - 10.1039/c4cp02405b
DO - 10.1039/c4cp02405b
M3 - Article
VL - 16
SP - 16629
EP - 16641
JO - Physical Chemistry Chemical Physics
JF - Physical Chemistry Chemical Physics
SN - 1463-9076
IS - 31
ER -