K.-C. Sham et al. / Polyhedron 30 (2011) 1149–1156
1155
1.30 (d, J = 7.2 Hz, 6H), 1.36 (s, 6H), 1.40 (s, 6H), 2.03 (m, 2H), 2.08
Appendix A. Supplementary data
(m, 2H), 2.5 (m, 4H), 2.62 (t, J = 6 Hz, 2H), 2.69 (m, J = 6 Hz, 2H),
2.84 (m, 2H), 3.14 (m, 2H), 6.22 (d, J = 7.6 Hz, 2H), 6.76
(d, J = 5.2 Hz, 2H), 6.78 (d, J = 4.8 Hz, 2H), 7.20 (m, 4H), 7.17 (d,
J = 8.0 Hz, 2H), 7.28 (m, 6H), 7.43 (t, J = 6 Hz, 2H), 7.57 (d,
J = 7.2 Hz, 2H), 7.70 (d, J = 6.8 Hz, 2H); 13C NMR (300 MHz, CDCl3,
a mixture of biphenyl conformers) d: 10.0, 10.1, 19.2, 20.0, 20.1,
26.2, 26.3, 30.4, 31.4, 31.5, 51.3, 51.4, 53.8, 56.5, 56.6, 76.6,
120.7, 126.4, 126.6, 127.1, 127.2, 127.3, 127.5, 129.2, 129.4,
131.5, 138.2, 140.3, 140.5, 141.6, 141.9, 155.0, 155.2, 168.9; Anal.
Calc. for C38H40N2ꢁ2H2O: C, 81.39; H, 7.91; N, 5.00; Found: C,
81.11; H, 7.71; N 5.23; Positive ion MS-ESI m/z: 525 (MH+).
CCDC 796015 and 796016 contain the supplementary crystallo-
graphic data for [Ag(L2)(ClO4)] and [Cu(L2)I] respectively. These
graphic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK;
fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
References
[1] J. Reedijk, G. Wilkinson (Eds.), Comprehensive Coordination Chemistry, vol. 2,
Pergamon Press, London, 1987. 73.
[2] A.G. Blackman, Eur. J. Inorg. Chem. (2008) 2633–2647.
[3] H.-L. Kwong, H.-L. Yeung, C.-T. Yeung, W.-S. Lee, C.-S. Lee, W.-L. Wong, Coor.
Chem. Rev. 251 (2007) 2188.
[4] O. Mamula, A. Von Zelewsky, Coor. Chem. Rev 242 (2003) 87.
[5] M.D. Ward, J.A. McCleverty, J.C. Jeffery, Coor. Chem. Rev. 222 (2001) 251.
[6] T.C. Stamatos, C.G. Efthymiou, C.C. Stoumpos, S.P. Perlepes, Eur. J. Inorg. Chem.
(2009) 3361.
8.6.3. Caution
Perchlorate salts are potentially explosive and should be treated
with extra care. Those complexes described below which were iso-
lated as perchlorates were only prepared in small amounts which
did not cause any problem in handling.
[7] C. Kaes, A. Katz, M.W. Hosseini, Chem. Rev 100 (2000) 3553.
[8] M. Ruben, J. Rojo, R. Salguero, L.H. Uppadine, J.-M. Lehn, Angew. Chem., Int. Ed.
43 (2004) 3644.
8.7. General procedure for [Ag(L)ClO4] (L = L1 and L2)
[9] Y. Guo, W. Dou, X. Zhou, W. Liu, W. Qln, Z. Zang, H. Zhang, D. Wang, Inorg.
Chem. 48 (2009) 3581.
[10] L.T. Dulatas, S.N. Brown, E. Ojomo, B.C. Noll, M.J. Cavo, P.B. Holt, M.M.
Wopperer, Inorg. Chem. 48 (2009) 10789.
[11] C. Vedder, F. Schaper, H.-H. Brintzinger, M. Kettunen, S. Babik, G. Fink, Eur. J.
Inorg. Chem. (2005) 1071.
[12] D.P. Goldberg, A. Caneschi, S.J. Lippard, J. Am. Chem. Soc. 115 (1993)
9299.
Methanol (2 ml) was added to a flask containing L (0.12 mmol)
and AgClO4 (0.12 mmol) that was covered with foil. The mixture
was stirred for 12 h. The white precipitated product was collected
by filtration and washed with diethyl ether (10 ml ꢂ 3).
8.7.1. [Ag(L1)ClO4]
The general procedure was followed with L1 (0.060 g). A white
solid (0.053 g, 0.076 mmol, 64%) was obtained: Anal. Calc. for
[13] S.-Q. Zang, L. Zhao, T.C.W. Mak, Organometallics 27 (2008) 2396.
[14] D. Cunningham, K. Gilligan, M. Hannon, C. Kelly, P. McArdle, A. O’Malley,
Organometallics 23 (2004) 984.
[15] C. Mukherjee, T. Weyhermüller, E. Bothe, P. Chaudhuri, Inorg. Chem. 47 (2008)
11620.
C
36H36N2AgClO4: C, 61.4; H, 5.15; N, 3.98. Found: C, 61.2; H,
5.15; N, 4.08. Positive ion MS-ESI m/z: 603 (MꢀClO4)+.
[16] E. Müller, C. Piguet, G. Bernardinelli, A.F. Williams, Inorg. Chem. 27 (1988)
849.
[17] J. Chen, R. Russo, W. Chao, L.D. Margerum, M.R. Malachowski, R. White, Z.
Thawley, A. Thayer, A.L. Rheingold, L.N. Zakharov, J. Chem. Soc., Dalton Trans.
(2007) 2571.
[18] P. Hormnirun, E.L. Marshall, V.C. Gibson, R.I. Pugh, A.J.P. White, Proc. Natl.
Acad. Sci. USA 103 (2006) 15343.
[19] Y.J. Zhang, F. Wang, W. Zhang, J. Org. Chem. 72 (2007) 9208.
[20] P.S. Singh, H.C. Rubeck, P. Huang, S. Ezzaher, L. Eriksson, M. Stein, S. Ott, R.
Lomoth, Inorg. Chem. 48 (2009) 10883.
[21] M. Maus, W. Rettig, J. Phys. Chem. A 106 (2002) 2104.
[22] Z.-H. Lin, L.-X. Xie, Y.-G. Zhao, C.-Y. Duan, J.-P. Qu, Org. Biomol. Chem. 5 (2007)
3535.
8.7.2. [Ag(L2)ClO4]
The general procedure was followed with L2 (0.063 g). A white
solid (0.066 g, 0.09 mmol, 75%) was obtained: Anal. Calc. for
C
38H40N2AgClO4ꢁ1/4CH2Cl2: C, 61.0; H, 5.42; N, 3.72. Found: C,
61.1; H, 5.43; N, 3.81. Positive ion MS-ESI m/z: 631 (MꢀClO4)+.
8.8. General procedure for [Cu(L)I] (L = L1 and L2)
[23] D.-Y. Wu, L.-X. Xie, C.-L. Zhang, C.-Y. Duan, Y.-G. Zhao, Z.-J. Guo, J. Chem. Soc.,
Dalton Trans. (2006) 3528.
Degassed MeCN (6 ml) was added to a flask containing L
(0.12 mmol) and CuI (0.12 mmol) under nitrogen. The mixture
was stirred for 12 h. It was reduced to minimum amount of sol-
vent. Dichloromethane (2 ml) was added, then n-hexane (40 ml)
was added to precipitate out the product. The product was col-
lected by filtration and washed with n-hexane (20 ml ꢂ 3).
[24] J. Cody, C.J. Fahrni, Tetrahedron 60 (2004) 11099.
[25] D.H. Lee, J.H. Im, J.-H. Lee, J.-I. Hong, Tetrahedron Lett. 43 (2002) 9637.
[26] T. Mizuno, M. Yamamoto, M. Takeuchi, S. Shinkai, Tetrahedron 56 (2000) 6193.
[27] A.M. Costero, J. Sanchis, S. Gil, V. Sanz, J.A. Gareth Williams, J. Mater. Chem. 15
(2005) 2848.
[28] M. Teng, G. Kuang, X. Jia, M. Gao, Y. Li, Y. Wei, J. Mater. Chem. 19 (2009)
5648.
[29] H.-L. Kwong, L.-S. Cheng, W.-S. Lee, W.-L. Wong, W.-T. Wong, Eur. J. Inorg.
Chem. (2000) 1997.
8.8.1. [Cu(L1)I]
[30] M. Düggeli, C. Goujon-Ginglinger, S.R. Ducotterd, D. Mauron, C. Bonte, A. von
Zelewsky, H. Steockli-Evans, A. Neels, Org. Biomol. Chem. (2003) 1894.
[31] J.W. Akitt, B.E. Mann, NMR and Chemistry: An introduction to modern NMR
spectroscopy, Stanley Thornes Ltd., Cheltenham, 2000.
[32] C.R.K. Glasson, L.F. Lindoy, G.V. Meehan, Coord. Chem. Rev 252 (2008) 940.
[33] T. Sugimoto, T. Suzuki, S. Shinkai, K. Sada, J. Am. Chem. Soc. 129 (2007)
270.
The general procedure was followed with L1 (0.061 g). A yellow
solid (0.050 g, 0.072 mmol, 60%) was obtained: Anal. Calc. for
C
36H36N2CuI: C, 62.9; H, 5.28; N, 4.08. Found: C, 62.7; H, 5.11; N,
3.92. Positive MS-ESI m/z: 559 (MꢀI)+.
[34] C.-S. Lee, P.-F. Teng, W.-L. Wong, H.-L. Kwong, A.S.C. Chan, Tetrahedron 61
(2005) 7924.
[35] W.-L. Wong, K.-H. Huang, P.-F. Teng, C.-S. Lee, H.-L. Kwong, Chem. Commun.
(2004) 384.
[36] T.W. Bell, A.B. Khasanov, M.G.B. Drew, J. Am. Chem. Soc. 124 (2002) 14092.
[37] T. Chang, A.M. Heiss, S.J. Cantrill, M.C.T. Fyfe, A.R. Pease, S.J. Rowan, J.F.
Stoddart, A.J.P. White, D.J. Williams, Org. Lett. 2 (2000) 2947.
[38] Binding constants: the measurement of molecular complex stability; Wiley:
New York, 1987.
8.8.2. [Cu(L2)I]
The general procedure was followed with L2 (0.063 g). A yellow
solid (0.055 g, 0.076 mmol, 63%) was obtained: Anal. Calc. for
C34H40N2CuIꢁ1/5CH2Cl2: C, 62.7; H, 5.56; N, 3.82. Found: C, 62.8;
H, 5.59; N, 3.82. Positive MS-ESI m/z: 587 (M ꢀ I)+.
Acknowledgment
Io=ðI ꢀ IoÞ ¼ ða=ðb ꢀ aÞÞð1=K½Gꢃꢀ1 þ 1Þ
Io=ðI ꢀ IoÞ ¼ ðc=ðd ꢀ cÞÞð1=K½Gꢃꢀ2 þ 1Þ
ð1Þ
ð2Þ
The work described in this paper was supported by a grant from
the University Grants Committee of the Hong Kong Special Admin-
istrative Region, China (Project No. [AoE/P-03/08]) and the City
University of Hong Kong (Project No.7002607).
where a, b, c and d are constants.