authors thank Dr Turki S. Al-Saud and Dr Mohamed B. Alfageeh
at KACST for their generous support of this program of research
at NU. This material is based upon research sponsored by the
Air Force Office of Scientific Research, under agreement number
FA9550-07-1-0534. This work was supported by the MRSEC
program of the National Science Foundation (DMR-0520513)
at the Materials Research Center of Northwestern University.
This material is based upon work supported as part of the Non-
Equilibrium Energy Research Center (NERC), an Energy Frontier
Research Center funded by the U.S. Department of Energy, Office
of Science, Office of Basic Energy Sciences under Award Number
DE-SC0000989. A.C.F. acknowledges support from a National
Science Foundation Graduate Research Fellowship.
Chem. Soc., 2007, 129, 15085–15090; (e) J. D. Crowley, K. D. Ha¨nni,
D. A. Leigh and A. M. Z. Slawin, J. Am. Chem. Soc., 2010, 132, 5309–
5314; (f) X. Wang, J. Zhu and D. B. Smithrud, J. Org. Chem., 2010, 75,
3358–3370.
6 (a) V. Serreli, C.-F. Lee, E. R. Kay and D. A. Leigh, Nature, 2007, 445,
523–527; (b) S. Saha, A. H. Flood, J. F. Stoddart, S. Impellizzeri, S.
Silvi, M. Venturi and A. Credi, J. Am. Chem. Soc., 2007, 129, 12159–
12171; (c) S. Saha and J. F. Stoddart, Chem. Soc. Rev., 2007, 36, 77–92;
(d) W. D. Zhou, D. G. Chen, J. B. Li, J. L. Xu, J. Lv, H. B. Liu and Y.
L. Li, Org. Lett., 2007, 9, 3929–3932; (e) Y.-L. Zhao and J. F. Stoddart,
Langmuir, 2009, 25, 8442–8446; (f) A. Coskun, D. C. Friedman, H. Li,
K. Patel, H. A. Khatib and J. F. Stoddart, J. Am. Chem. Soc., 2009,
131, 2493–2495; (g) V. Balzani, A. Credi and M. Venturi, Chem. Soc.
Rev., 2009, 38, 1542–1550; (h) X. Ma, Q. C. Wang and H. Tian, Prog.
Chem., 2009, 21, 106–115; (i) S. J. Li, D. Taura, A. Hashidzume and A.
Harada, Chem.–Asian J., 2010, 5, 2281–2289.
7 (a) A. A. Farrell, E. R. Kay, G. Bottari, D. A. Leigh and S. P. Jarvis,
Appl. Surf. Sci., 2007, 253, 6090–6095; (b) C. Wang, M. A. Olson, L.
Fang, D. Ben´ıtez, E. Tkatchouk, S. Basu, A. N. Basuray, D. Zhang, D.
Zhu, W. A. Goddard III and J. F. Stoddart, Proc. Natl. Acad. Sci. U. S.
A., 2010, 107, 13991–13996.
Notes and references
1 (a) V. Balzani, M. Go´mez-Lo´pez and J. F. Stoddart, Acc. Chem. Res.,
1998, 31, 405–414; (b) M. Fujita, Acc. Chem. Res., 1999, 32, 53–61; (c) B.
L. Feringa, Molecular Switches, Wiley-VCH Verlag GmbH, Weinheim,
Germany, 2001; (d) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y.
Luo, C. P. Collier and J. R. Heath, Acc. Chem. Res., 2001, 34, 433–
444; (e) R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi and M.
Venturi, Acc. Chem. Res., 2001, 34, 445–455; (f) C. A. Schalley, K.
Beizai and F. Vo¨gtle, Acc. Chem. Res., 2001, 34, 465–476; (g) J. P.
Collin, C. Dietrich-Buchecker, P. Gavin˜a, M. C. Jimenez-Molero and
J.-P. Sauvage, Acc. Chem. Res., 2001, 34, 477–487; (h) S. Shinkai, M.
Ikeda, A. Sugasaki and M. Takeuchi, Acc. Chem. Res., 2001, 34, 494–
503; (i) B. L. Feringa, Acc. Chem. Res., 2001, 34, 504–513; (j) K. Kinbara
and T. Aida, Chem. Rev., 2005, 105, 1377–1400; (k) H. Tian and Q. C.
Wang, Chem. Soc. Rev., 2006, 35, 361–374; (l) V. Balzani, A. Credi and
M. Venturi, Molecular Devices and Machines. Concepts and Perspectives
for the Nanoworld, Wiley-VCH Verlag GmbH, Weinheim, Germany,
2008; (m) A. Rescifina, C. Zagni, D. Iannazzo and P. Merino, Curr.
Org. Chem., 2009, 13, 448–481; (n) M. A. Olson, A. B. Braunschweig,
T. Ikeda, L. Fang, A. Trabolsi, A. M. Z. Slawin, S. I. Khan and J.
F. Stoddart, Org. Biomol. Chem., 2009, 7, 4391–4405; (o) S. Silvi, M.
Venturi and A. Credi, J. Mater. Chem., 2009, 19, 2279–2294; (p) Y.
Tokunaga, J. Synth. Org. Chem. Jpn., 2011, 69, 62–72.
8 (a) M.-V. Mart´ınez-D´ıaz, N. Spencer and J. F. Stoddart, Angew. Chem.,
Int. Ed. Engl., 1997, 36, 1904–1907; (b) P. R. Ashton, R. Ballardini, V.
Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Go´mez-
Lo´pez, M.-V. Mart´ınez-D´ıaz, A. Piersanti, N. Spencer, J. F. Stoddart,
M. Venturi, A. J. P. White and D. J. Williams, J. Am. Chem. Soc., 1998,
120, 11932–11942; (c) J. D. Badjic´, V. Balzani, A. Credi, S. Silvi and J.
F. Stoddart, Science, 2004, 303, 1845–1849; (d) C. M. Keaveney and D.
A. Leigh, Angew. Chem., Int. Ed., 2004, 43, 1222–1224; (e) J. D. Badjic´,
C. M. Ronconi, J. F. Stoddart, V. Balzani, S. Silvi and A. Credi, J. Am.
Chem. Soc., 2006, 128, 1489–1499; (f) F. Coutrot, C. Romuald and E.
Busseron, Org. Lett., 2008, 10, 3741–3744; (g) Q. Jiang, H.-Y. Zhang,
M. Han, Z.-J. Ding and Y. Liu, Org. Lett., 2010, 12, 1728–1731.
9 (a) R. A. Bissell, E. Co´rdova, A. E. Kaifer and J. F. Stoddart, Nature,
1994, 369, 133–137; (b) A. Altieri, F. G. Gatti, E. R. Kay, D. A. Leigh,
D. Martel, F. Paolucci, A. M. Z. Slawin and J. K. Y. Wong, J. Am. Chem.
Soc., 2003, 125, 8644–8654; (c) T. Iijima, S. A. Vignon, H.-R. Tseng, T.
Jarrosson, J. K. M. Sanders, F. Marchioni, M. Venturi, E. Apostoli, V.
Balzani and J. F. Stoddart, Chem.–Eur. J., 2004, 10, 6375–6392; (d) I.
Aprahamian, W. R. Dichtel, T. Ikeda, J. R. Heath and J. F. Stoddart,
Org. Lett., 2007, 9, 1287–1290; (e) G. Fioravanti, N. Haraszkiewicz, E.
R. Kay, S. M. Mendoza, C. Bruno, M. Marcaccio, P. G. Wiering, F.
Paolucci, P. Rudolf, A. M. Brouwer and D. A. Leigh, J. Am. Chem.
Soc., 2008, 130, 2593–2601; (f) F. Durola, J. Lux and J.-P. Sauvage,
Chem.–Eur. J., 2009, 15, 4124–4134; (g) B. Korybut-Daszkiewicz, R.
Bilewicz and K. Woz´niak, Coord. Chem. Rev., 2010, 254, 1637–1660.
10 L. L. Grill, K.-H. Rieder, F. Moresco, G. Rapenne, S. Stojkovic, C.
Joachim and X. Bouju, Nat. Nanotechnol., 2007, 2, 95–98.
11 (a) C. Joachim, J. K. Gimzewski and A. Aviram, Nature, 2000, 408,
541–548; (b) J. Repp, G. Meyer, S. M. Stojkovic´, A. Gourdon and
C. Joachim, Phys. Rev. Lett., 2005, 94, 026803-1–026803-4; (c) C. J.
Villagomez, T. Zambelli, S. Gauthier, A. Gourdon, S. Stojkovic, C.
Barthes and C. Joachim, Chem. Phys. Lett., 2007, 450, 107–111; (d) A.
Bellec, F. Ample, D. Riedel, G. Dujardin and C. Joachim, Nano Lett.,
2009, 9, 144–147; (e) L. Lafferentz, F. Ample, H. Yu, S. Hecht, C.
Joachim and L. Grill, Science, 2009, 323, 1193–1197.
12 (a) M. Alemani, S. Selvanathan, F. Ample, M. V. Peters, K.-H. Rieder,
F. Moresco, C. Joachim, S. Hecht and L. Grill, J. Phys. Chem. C, 2008,
112, 10509–10514; (b) B.-Y. Choi1, S.-J. Kahng, S. Kim, H. Kim, H. W.
Kim, Y. J. Song, J. Ihm and Y. Kuk, Phys. Rev. Lett., 2006, 96, 156106-
1–156106-4; (c) M. El Garah, B. Baris, V. Luzet, F. Palmino and F.
Che´rioux, ChemPhysChem, 2010, 11, 2568–2572; (d) E. McNellis, J.
Meyer, A. D. Baghi and K. Reuter, Phys. Rev. B: Condens. Matter
Mater. Phys., 2009, 80, 035414-1–035414-10; (e) M. Piantek, G. Schulze,
M. Koch, K. J. Franke, F. Leyssner, A. Kru¨ger, C. Nav´ıo, J. Miguel, M.
Bernien, M. Wolf, W. Kuch, P. Tegeder and J. I. Pascual, J. Am. Chem.
Soc., 2009, 131, 12729–12735.
2 (a) J. Berna´, D. A. Leigh, M. Lubomska, S. M. Mendoza, E. M. Pe´rez,
P. Rudolf, G. Teobaldi and F. Zerbetto, Nat. Mater., 2005, 4, 704–710;
(b) P. Wan, Y. Jiang, Y. Wang, Z. Wang and X. Zhang, Chem. Commun.,
2008, 5710–5712.
3 (a) C. P. Collier, G. Mattersteig, E. W. Wong, Y. Luo, K. Beverly, J.
Sampaio, F. M. Raymo, J. F. Stoddart and J. R. Heath, Science, 2000,
289, 1172–1175; (b) J. E. Green, J. W. Choi, A. Boukai, Y. Bunimovich,
E. Johnston-Halperin, E. DeIonno, Y. Luo, B. A. Sheriff, K. Xu, Y. S.
Shin, H.-R. Tseng, J. F. Stoddart and J. R. Heath, Nature, 2007, 445,
414–417; (c) W. R. Dichtel, J. R. Heath and J. F. Stoddart, Philos. Trans.
R. Soc. London, Ser. A, 2007, 365, 1607–1625; (d) Y. H. Jang and W.
A. Goddard, J. Phys. Chem. C, 2010, 114, 4611–4616; (e) S. J. van der
Molen and P. Liljeroth, J. Phys.: Condens. Matter, 2010, 22, 1–30; (f) W.
Y. Zhang, E. DeIonno, W. R. Dichtel, L. Fang, A. Trabolsi, J.-C. Olsen,
D. Ben´ıtez, J. R. Heath and J. F. Stoddart, J. Mater. Chem., 2011, 21,
1487–1495.
4 (a) R. Hernandez, H.-R. Tseng, J. W. Wong, J. F. Stoddart and J. I. Zink,
J. Am. Chem. Soc., 2004, 126, 3370–3371; (b) K. Patel, S. Angelos, W.
R. Dichtel, A. Coskun, Y.-W. Yang, J. I. Zink and J. F. Stoddart, J.
Am. Chem. Soc., 2008, 130, 2382–2383; (c) Y. Klichko, M. Liong, E.
Choi, S. Angelos, A. E. Nel, J. F. Stoddart, F. Tamanoi and J. I. Zink,
J. Am. Ceram. Soc., 2009, 92, S2–S10; (d) K. K. Cot´ı, M. E. Belowich,
M. Liong, M. W. Ambrogio, Y. A. Lau, H. A. Khatib, J. I. Zink, N.
M. Khashab and J. F. Stoddart, Nanoscale, 2009, 1, 16–39; (e) M. M.
Boyle, R. A. Smaldone, A. C. Whalley, M. W. Ambrogio, Y. Y. Botros
and J. F. Stoddart, Chem. Sci., 2011, 2, 204–210.
13 (a) B. Odell, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F.
Stoddart and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1988, 27,
1547–1550; (b) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani,
M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp,
M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N.
Spencer, J. F. Stoddart, C. Vicent and D. J. Williams, J. Am. Chem. Soc.,
1992, 114, 193–218; (c) M. Asakawa, W. Dehaen, G. L’abbe´, S. Menzer,
J. Nouwen, F. M. Raymo, J. F. Stoddart and D. J. Williams, J. Org.
5 (a) N. Armaroli, V. Balzani, J.-P. Collin, P. Gavin˜a, J.-P. Sauvage and B.
Ventura, J. Am. Chem. Soc., 1999, 121, 4397–4408; (b) S. A. Vignon, T.
Jarrosson, T. Iijima, H.-R. Tseng, J. K. M. Sanders and J. F. Stoddart, J.
Am. Chem. Soc., 2004, 126, 9884–9885; (c) D. S. Marlin, D. G. Cabrera,
D. A. Leigh and A. M. Z. Slawin, Angew. Chem., Int. Ed., 2006, 45,
77–83; (d) J. D. Crowley, D. A. Leigh, P. J. Lusby, R. T. McBurney, L.-
E. Perret-Aebi, C. Petzold, A. M. Z. Slawin and M. D. Symes, J. Am.
7132 | Org. Biomol. Chem., 2011, 9, 7126–7133
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