Journal of the American Chemical Society
Communication
(16) Marques
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-Gonzal
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ez, S.; Yufit, D. S.; Howard, J. K.; Martín, S.;
ASSOCIATED CONTENT
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Osorio, H. M.; García-Suarez, V. M.; Nichols, R. J.; Higgins, S. J.; Cea,
P.; Low, P. J. Dalton Trans. 2013, 42, 338.
S
* Supporting Information
Synthetic procedures, STM-BJ procedures, table of conductan-
ces, additional figures, characterization data, computational
details, and crystallographic data (CIF). This material is
(17) Vonlanthen, D.; Rotzler, J.; Neuburger, M.; Mayor, M. Eur. J.
Org. Chem. 2010, 2010, 120.
(18) Venkataraman, L.; Klare, J. E.; Nuckolls, C.; Hybertsen, M. S.;
Steigerwald, M. L. Nature 2006, 442, 904.
(19) Ke, S.; Yang, W.; Baranger, H. U. Nano Lett. 2008, 8, 3257.
(20) Solomon, G. C.; Andrews, D. Q.; Goldsmith, R. H.; Hansen, T.;
Wasielewski, M. R.; Van Duyne, R. P.; Ratner, M. A. J. Am. Chem. Soc.
2008, 130, 17301.
(21) Aradhya, S. V; Meisner, J. S.; Krikorian, M.; Ahn, S.;
Parameswaran, R.; Steigerwald, M. L.; Nuckolls, C.; Venkataraman,
L. Nano Lett. 2012, 12, 1643.
AUTHOR INFORMATION
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Corresponding Authors
́
(22) Guedon, C. M.; Valkenier, H.; Markussen, T.; Thygesen, K. S.;
Hummelen, J. C.; van der Molen, S. J. Nat. Nanotechnol. 2012, 7, 305.
(23) Roy, X.; Schenck, C. L.; Ahn, S.; Lalancette, R. A.;
Venkataraman, L.; Nuckolls, C.; Steigerwald, M. L. Angew. Chem.,
Int. Ed. 2012, 51, 12473.
Present Address
§Department of Chemistry, The Johns Hopkins University,
Baltimore, MD 21218, USA.
(24) Klausen, R. S.; Widawsky, J. R.; Su, T. A.; Li, H.; Chen, Q.;
Steigerwald, M. L.; Venkataraman, L.; Nuckolls, C., unpublished
results.
(25) Myers, A. G.; Kephart, S. E.; Chen, H. J. Am. Chem. Soc. 1992,
114, 7922.
(26) Denmark, S. E.; Griedel, B. D.; Coe, D. M. J. Org. Chem. 1993,
58, 988.
(27) Matsumoto, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1994, 59,
7152.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The STM-BJ experiments were supported as part of the Center
for Re-Defining Photovoltaic Efficiency Through Molecular-
Scale Control, as Energy Frontier Research Center funded by
the U.S. Department of Energy (DOE), Office of Science,
Office of Basic Energy Science under Award Number DE-
SC0001085. T.A.S. is supported by the NSF Graduate Research
Fellowship under Grant No. 11-44155. H.L. is supported by the
Semiconductor Research Corporation and New York CAIST
program. J.L.L. acknowledges support from NSF Grant CHE-
11-52949. We thank Arunabh Batra for helpful discussions and
Dr. Yasuhiro Itagaki for mass spectrometry assistance. We
thank the NSF (CHE-0619638) for acquisition of an X-ray
diffractometer and Dr. Wesley Sattler and Serge Ruccolo for
crystallographic analysis of 1 and 5.
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