Luminescent Os(II) and Ir(III) complexes containing a tripodal-type structure terminalized with three thiol derivatives are described. The tripod is introduced through derivatization, with a rigid spacer, of a phenanthroline ligand coordinated to the metal ion, and the entire structure possesses axial geometry. The geometry of the complexes combined with the three anchoring sites, the thiol groups, allows the complexes to adopt an almost perpendicular arrangement to the surfaces and the formation of a well-packed monolayer on Au substrates. The photophysical and electrochemical behavior of the complexes is studied in solution and on surfaces. Furthermore, a self-assembled monolayer (SAM) of Os(II) complexes on an ultraflat Au surface is used to fabricate a metal–molecule–metal junction with Au and In Ga eutectic as electrodes. The Os(II) SAM in the tunneling junction exhibits rectification behavior which is opposite in direction to that which we have previously shown for Ru(II) SAMs.
Conference
IUPAC Symposium on Photochemistry, International Symposium on Photochemistry, PHOTO, Photochemistry, XXIIIrd, Ferrara, Italy, 2010-07-11–2010-07-16
References
1 10.1146/annurev.pc.43.100192.003443, C. A. Mirkin, M. A. Ratner. Annu. Rev. Phys. Chem.43, 719 (1992).Search in Google Scholar
2 10.1038/35046000, C. Joachim, J. K. Gimzewski, A. Aviram. Nature408, 541 (2000).Search in Google Scholar PubMed
3 10.1146/annurev.physchem.58.032806.104523, F. Chen, J. Hihath, Z. Huang, X. Li, N. J. Tao. Annu. Rev. Phys. Chem.58, 535 (2007).Search in Google Scholar PubMed
4 10.1098/rsta.2007.2034, W. R. Dichtel, J. R. Heath, J. Fraser Stoddart. Philos. Trans. R. Soc. A365, 1607 (2007).Search in Google Scholar PubMed
5 10.1016/j.jorganchem.2007.07.055, T. Y. Dong, C. L. Huang, C. P. Chen, M. C. Lin. J. Organomet. Chem.692, 5147 (2007).Search in Google Scholar
6 10.1021/cr0300789, J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, G. M. Whitesides. Chem. Rev.105, 1103 (2005).Search in Google Scholar PubMed
7 10.1021/cr9502357, A. Ulman. Chem. Rev.96, 1533 (1996).Search in Google Scholar PubMed
8 10.1021/ja8018093, J. M. Mativetsky, G. Pace, M. Elbing, M. A. Rampi, M. Mayor, P. Samori. J. Am. Chem. Soc.130, 9192 (2008).Search in Google Scholar PubMed
9 10.1103/PhysRevLett.88.176804, J. Reichert, R. Ochs, D. Beckmann, H. B. Weber, M. Mayor, H. v. Löhneysen. Phys. Rev. Lett.88, 176804 (2002).Search in Google Scholar PubMed
10 10.1002/ejoc.200900751, N. Weibel, A. Mishchenko, T. Wandlowski, M. Neuburger, Y. Leroux, M. Mayor. Eur. J. Org. Chem. 6140 (2009).Search in Google Scholar
11 10.1038/nnano.2008.237, S. Wu, M. T. Gonzalez, R. Huber, S. Grunder, M. Mayor, C. Schonenberger, M. Calame. Nat. Nano.3, 569 (2008).Search in Google Scholar PubMed
12 10.1038/nmat2332, N. Tuccitto, V. Ferri, M. Cavazzini, S. Quici, G. Zhavnerko, A. Licciardello, M. A. Rampi. Nat. Mater.8, 41 (2009).Search in Google Scholar PubMed
13 10.1021/ja804075y, E. Tran, A. E. Cohen, R. W. Murray, M. A. Rampi, G. M. Whitesides. J. Am. Chem. Soc.131, 2141 (2009).Search in Google Scholar PubMed
14 10.1002/cphc.200900974, S. Ballmann, W. Hieringer, D. Secker, Q. Zheng, J. A. Gladysz, A. Görling, H. B. Weber. ChemPhysChem11, 2256 (2010).Search in Google Scholar PubMed
15 D. Secker, H. B. Weber. Phys. Status Solidi B244, 4176 (2007).10.1002/pssb.200776207Search in Google Scholar
16 10.1103/PhysRevB.81.205430, J. S. Seldenthuis, H. S. J. van der Zant, M. A. Ratner, J. M. Thijssen. Phys. Rev. B81, 205430 (2010).Search in Google Scholar
17 10.1126/science.272.5265.1145, G. E. Poirier, E. D. Pylant. Science272, 1145 (1996).Search in Google Scholar PubMed
18 10.1021/ja00246a011, M. D. Porter, T. B. Bright, D. L. Allara, C. E. D. Chidsey. J. Am. Chem. Soc.109, 3559 (1987).Search in Google Scholar
19 10.1021/ja00200a039, C. D. Bain, J. Evall, G. M. Whitesides. J. Am. Chem. Soc.111, 7155 (1989).Search in Google Scholar
20 10.1021/ja00019a011, P. E. Laibinis, G. M. Whitesides, D. L. Allara, Y. T. Tao, A. N. Parikh, R. G. Nuzzo. J. Am. Chem. Soc.113, 7152 (1991).Search in Google Scholar
21 10.1021/la048762l, E. Figgemeier, E. C. Constable, C. E. Housecroft, Y. C. Zimmermann. Langmuir20, 9242 (2004).Search in Google Scholar PubMed
22 10.1039/b807526c, K. Terada, K. Kobayashi, M.-a. Haga. Dalton Trans. 4846 (2008).Search in Google Scholar PubMed
23 A. D’Aleo, R. M. Williams, Y. Chriqui, Vijay M. Iyer, P. Belser, F. Vergeer, V. Ruiz, P. R. Unwin, L. De Cola. Open Inorg. Chem. J.1, 26 (2007).Search in Google Scholar
24 10.1021/ic1002868, S. Ramachandra, K. C. Schuermann, F. Edafe, P. Belser, C. A. Nijhuis, W. F. Reus, G. M. Whitesides, L. De Cola. Inorg. Chem.50, 1581 (2011).Search in Google Scholar PubMed
25 10.1021/la0007170, R. J. Forster, E. Figgemeier, A. C. Lees, J. Hjelm, J. G. Vos. Langmuir16, 7867 (2000).Search in Google Scholar
26 10.1021/la000718s, R. J. Forster, E. Figgemeier, P. Loughman, A. Lees, J. Hjelm, J. G. Vos. Langmuir16, 7871 (2000).Search in Google Scholar
27 10.1007/s10008-007-0339-8, A. Ricci, C. Rolli, S. Rothacher, L. Baraldo, C. Bonazzola, E. Calvo, N. Tognalli, A. Fainstein. J. Solid State Electrochem.11, 1511 (2007).Search in Google Scholar
28 10.1021/jp951708g, J. E. Hudson, H. D. Abruna. J. Phys. Chem.100, 1036 (1996).Search in Google Scholar
29 10.1021/jp952541u, J. D. Tirado, H. D. Abruna. J. Phys. Chem.100, 4556 (1996).Search in Google Scholar
30 10.1021/la00018a057, J. D. Tirado, D. Acevedo, R. L. Bretz, H. D. Abruna. Langmuir10, 1971 (1994).Search in Google Scholar
31 10.1021/j100176a098, D. Acevedo, H. D. Abruna. J. Phys. Chem.95, 9590 (1991).Search in Google Scholar
32 10.1039/b505451f, T. Albrecht, K. Moth-Poulsen, J. B. Christensen, A. Guckian, T. Bjornholm, J. G. Vos, J. Ulstrup. Faraday Discuss.131, 265 (2006).Search in Google Scholar PubMed
33 10.1021/ic060903e, N. M. O’Boyle, T. Albrecht, D. H. Murgida, L. Cassidy, J. Ulstrup, J. G. Vos. Inorg. Chem.46, 117 (2006).Search in Google Scholar PubMed
34 10.1021/jo051863j, T. Kitagawa, Y. Idomoto, H. Matsubara, D. Hobara, T. Kakiuchi, T. Okazaki, K. Komatsu. J. Org. Chem.71, 1362 (2006).Search in Google Scholar PubMed
35 10.1021/la9707787, M. A. Fox, J. K. Whitesell, A. J. McKerrow. Langmuir14, 816 (1998).Search in Google Scholar
36 10.1021/la0475573, J. S. Park, A. N. Vo, D. Barriet, Y. S. Shon, T. R. Lee. Langmuir21, 2902 (2005).Search in Google Scholar PubMed
37 10.1021/ja025840n, E. Galoppini, W. Guo, W. Zhang, P. G. Hoertz, P. Qu, G. J. Meyer. J. Am. Chem. Soc.124, 7801 (2002).Search in Google Scholar PubMed
38 10.1039/b515727g, T. Weidner, A. Kramer, C. Bruhn, M. Zharnikov, A. Shaporenko, U. Siemeling, F. Trager. Dalton Trans. 2767 (2006).Search in Google Scholar PubMed
39 10.1021/jo034169h, H. Jian, J. M. Tour. J. Org. Chem.68, 5091 (2003).Search in Google Scholar PubMed
40 10.1021/ja047156+, M. S. Lowry, W. R. Hudson, R. A. Pascal, S. Bernhard. J. Am. Chem. Soc.126, 14129 (2004).Search in Google Scholar PubMed
41 K. Kalyanasundaram. In Photochemistry of Polypyridine and Porphyrin Complexes, Academic Press, New York (1972).Search in Google Scholar
42 Y. Nakabayashi, K. Nakamura, M. Kawachi, T. Motoyama, O. Yamauchi. J. Biol. Inorg. Chem.8, 45 (2003).Search in Google Scholar
43 10.1246/bcsj.65.1006, M. Yamada, Y. Tanaka, Y. Yoshimoto, S. Kuroda, I. Shimao. Bull. Chem. Soc. Jpn.65, 1006 (1992).Search in Google Scholar
44 10.1021/j100407a046, E. M. Kober, J. V. Caspar, R. S. Lumpkin, T. J. Meyer. J. Phys. Chem.90, 3722 (1986).Search in Google Scholar
45 10.1021/ja0677261, E. A. Weiss, R. C. Chiechi, G. K. Kaufman, J. K. Kriebel, Z. Li, M. Duati, M. A. Rampi, G. M. Whitesides. J. Am. Chem. Soc.129, 4336 (2007).Search in Google Scholar
46 10.1021/la701919r, E. A. Weiss, G. K. Kaufman, J. K. Kriebel, Z. Li, R. Schalek, G. M. Whitesides. Langmuir23, 9686 (2007).Search in Google Scholar
47 10.1002/anie.200703642, R. C. Chiechi, E. A. Weiss, M. D. Dickey, G. M. Whitesides. Angew. Chem., Int. Ed.47, 142 (2008).Search in Google Scholar
48 10.1021/ma001662b, W. Y. Huang, W. Gao, T. K. Kwei, Y. Okamoto. Macromolecules34, 1570 (2001).Search in Google Scholar
49 K. Kalyanasundaram. In Photophysics and Photochemistry of Polypyridyl and Porphyrin Complexes, p. 626, Academic Press, New York (1992).Search in Google Scholar
50 D. Kumaresan, K. Shankar, S. Vaidya, R. Schmehl. In Photochemistry and Photophysics of Coordination Compounds II, Series Topics in Current Chemistry, Vol. 281, V. Balzani, S. Campagna (Eds.), pp. 101–142 (2007).10.1007/128_2007_140Search in Google Scholar
51 10.1002/chem.200901937, S. Verma, P. Kar, Amitava Das, D. K. Palit, H. N. Ghosh. Chem.—Eur. J.16, 611 (2010).Search in Google Scholar
52 10.1021/jp901135n, P. Kar, S. Verma, A. Das, H. N. Ghosh. J. Phys. Chem. C113, 7970 (2009).Search in Google Scholar
53 10.1016/S0010-8545(02)00106-6, H. Yersin, C. Kratzer. Coord. Chem. Rev.229, 75 (2002).Search in Google Scholar
54 10.1007/128_2007_131, L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, F. Barigelletti. Top. Curr. Chem.281, 143 (2007).Search in Google Scholar
55 10.1021/ic00293a008, F. O. Garces, K. A. King, R. J. Watts. Inorg. Chem.27, 3464 (1988).Search in Google Scholar
56 10.1021/j100308a012, K. Ichimura, T. Kobayashi, K. A. King, R. J. Watts. J. Phys. Chem.91, 6104 (2002).Search in Google Scholar
57 10.1039/b503065j, F. Lafolet, S. Welter, Z. Popovic, L. De Cola. J. Mater. Chem.15, 2820 (2005).Search in Google Scholar
58 10.1021/ic00295a022, A. Juris, S. Campagna, I. Bidd, J. M. Lehn, R. Ziessel. Inorg. Chem.27, 4007 (1988).Search in Google Scholar
59 10.1021/jp064878+, P. Pramod, P. K. Sudeep, K. G. Thomas, P. V. Kamat. J. Phys. Chem. B110, 20737 (2006).Search in Google Scholar PubMed
60 10.1021/jp057276j, P. Bertoncello, E. T. Kefalas, Z. Pikramenou, P. R. Unwin, R. J. Forster. J. Phys. Chem. B110, 10063 (2006).Search in Google Scholar PubMed
61 A. D’Aleo, R. M. Williams, Y. Chriqui, Vijay M. Iyer, P. Belser, F. Vergeer, V. Ruiz, P. R. Unwin, L. De Cola. Open Inorg. Chem. J.1, 26 (2007).Search in Google Scholar
62 10.1126/science.251.4996.919, C. E. D. Chidsey. Science251, 919 (1991).Search in Google Scholar PubMed
63 10.1021/ja00035a001, H. O. Finklea, D. D. Hanshew. J. Am. Chem. Soc.114, 3173 (1992).Search in Google Scholar
64 10.1021/ic00153a012, D. P. Rillema, G. Allen, T. J. Meyer, D. C. Conrad. Inorg. Chem.22, 1617 (1983).Search in Google Scholar
65 10.1039/dt9900001841, E. Amouyal, A. Homsi, J.-C. Chambron, J.-P. Sauvage. J. Chem. Soc., Dalton Trans. 1841 (1990).Search in Google Scholar
66 10.1021/ic00271a029, F. Barigelletti, A. Juris, V. Balzani, P. Belser, A. v. Zelewsky. Inorg. Chem.27, 4115 (1987).Search in Google Scholar
67 10.1039/a605269j, J.-Z. Wu, B.-H. Ye, L. Wang, L.-N. Ji, J.-Y. Zhou, R.-H. Li, Z.-Y. Zhou. J. Chem. Soc., Dalton Trans. 1395 (1997).Search in Google Scholar
68 10.1002/hlca.200790188, L.-F. Tan, S. Zhang, H. Chao, K.-C. Zheng, F. Wang, Y. Xiao, L.-N. Ji. Helv. Chim. Acta90, 1786 (2007).Search in Google Scholar
69 10.1002/anie.200904156, K. Omer, S. Y. Ku, K. T. Wong, A. Bard. Angew. Chem., Int. Ed.48, 9300 (2009).Search in Google Scholar
70 10.1002/(SICI)1521-4095(199802)10:3<219::AID-ADMA219>3.0.CO;2-6, M. Thelakkat, H.-W. Schmidt. Adv. Mater.10, 219 (1998).Search in Google Scholar
71 A. J. Bard, L. R. Faulkner. Electrochemical Methods, Fundamentals and Applications, John Wiley, New York (2001).Search in Google Scholar
72 10.1021/la00081a009, L. Strong, G. M. Whitesides. Langmuir4, 546 (1988).Search in Google Scholar
73 10.1021/la00054a029, D. M. Collard, M. A. Fox. Langmuir7, 1192 (1991).Search in Google Scholar
74 10.1016/S0022-0728(97)00553-6, D. Hobara, M. Ota, S.-i. Imabayashi, K. Niki, T. Kakiuchi. J. Electroanal. Chem.444, 113 (1998).Search in Google Scholar
75 10.1021/ja9048898, C. A. Nijhuis, W. F. Reus, G. M. Whitesides. J. Am. Chem. Soc.131, 17814 (2009).Search in Google Scholar
76 10.1021/ja0395792, A. V. Walker, T. B. Tighe, O. M. Cabarcos, M. D. Reinard, B. C. Haynie, S. Uppili, N. Winograd, D. L. Allara. J. Am. Chem. Soc.126, 3954 (2004).Search in Google Scholar
77 10.1063/1.2696653, J. M. Beebe, J. G. Kushmerick. Appl. Phys. Lett.90, 083117 (2007).Search in Google Scholar
78 10.1021/nl035117a, C. N. Lau, D. R. Stewart, R. S. Williams, M. Bockrath. Nano Lett.4, 569 (2004).Search in Google Scholar
79 10.1088/0957-4484/18/31/315204, T. W. Kim, G. Wang, H. Lee, T. Lee. Nanotechnology18, 315204 (2007).Search in Google Scholar
80 10.1063/1.2141955, R. Liu, S.-H. Ke, W. Yang, H. U. Baranger. J. Chem. Phys.124, 024718 (2006).Search in Google Scholar PubMed
81 10.1103/PhysRevB.66.165436, P. E. Kornilovitch, A. M. Bratkovsky, R. S. Williams. Phys. Rev. B66, 165436 (2002).Search in Google Scholar
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