Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 16, Issue 31, Pages 16629-16641Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cp02405b
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Funding
- TomKat Charitable Trust
- facilities and staff of the Yale University Faculty of Arts and Sciences High Performance Computing Center
- National Science Foundation [CNS 08-21132]
- Generalitat Valenciana project [ISIC/2012/008]
- Office of Basic Energy Sciences of the U.S. Department of Energy [DE-FG02-07ER15909]
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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.
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