Paper
RSC Advances
4
4
0
0
¨
¨
6.573 (d, 2H, J ¼ 3.0 Hz, H-4C ), 6.568 (d, 2H, J ¼ 2.4 Hz, H-4G),
R. Schirrmacher, B. Wangler and C. Wangler, Molecules,
2013, 18, 6469; (h) E. W. Price and C. Orvig, Chem. Soc.
Rev., 2014, 43, 260.
4
4
6.452 (d, 2H, J ¼ 2.4 Hz, H-4G ), 6.388 (d, 2H, J ¼ 1.8 Hz, H-4C),
5.555 (d, 2H, 2J ¼ 12.6 Hz, H-8A), 5.407 (d, 2H, 2J ¼ 16.2 Hz, H-
8G), 5.275 (d, 2H, 2J ¼ 12.0 Hz, H-3Da), *4.834 (dd, 2H, 3J ¼ 10.8
Hz, 3J ¼ 10.8 Hz, H-12ꢂ), *4.748 (d, 2H, 3J ¼ 10.2 Hz, 3J ¼ 6.0 Hz,
H-12+), 4.674 (d, 2H, 3J ¼ 3.0 Hz, H-12x), 4.634 (d, 2H, 2J ¼ 13.2
3 (a) K. F. Fouche, H. J. Le Roux and F. Phillips, J. Inorg. Nucl.
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P. Jewula, J.-C. Berthet, J.-C. Chambron, P. Thuery,
Y. Rousselin and M. Meyer, manuscript in preparation.
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R. J. Abergel, P. W. Durbin, B. Kullgren, S. N. Ebbe, J. Xu,
P. Y. Chang, D. Y. Bunin, E. A. Blakely, K. A. Bjornstad,
C. J. Rosen, D. K. Shuh and K. N. Raymond, Health Phys.,
2010, 99, 401.
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Chem. Biol., 1995, 2, 553.
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Eur. J. Org. Chem., 2011, 3191.
9 S. Dhungana, M. J. Miller, L. Dong, C. Ratledge and
A. L. Crumbliss, J. Am. Chem. Soc., 2003, 125, 7654.
2
2
0
Hz, H-3Fa), 4.528 (d, 2H, J ¼ 12.6 Hz, H-8A ), 4.445 (d, 2H, J ¼
13.2 Hz, H-3Ba), 4.328 (d, 2H, 2J ¼ 12.6 Hz, H-8C), 4.157 (d, 2H, 2J
2
0
¼ 13.2 Hz, H-3Ha), 4.142 (d, 2H, J ¼ 12.0 Hz, H-8C ), 3.981 (d,
2
0
´
2H, J ¼ 13.8 Hz, H-8E ), 3.841 (br dd, 4H, H-12C, H-15), 3.75–
2
3.50 (m, 14H, H-15, H-150), 3.662 (d, 2H, J ¼ 16.2 Hz, H-8G ),
3.436 (d, 4H, 2J ¼ 13.8 Hz, H-3Be, H-3Fe), 3.163 (d, 2H, 2J ¼ 12.6
Hz, H-3De), 3.157 (d, 2H, 2J ¼ 13.2 Hz, H-3He), 2.780 (tt, 2H, 2J ¼
13.8 Hz, H-13x), 2.676 (br q, 2H, H-13+), 2.137 (hidden, 4H, H-
0
´
+
x
13ꢂ, H-13 ), 2.048 (hidden, 2H, H-14 ), 2.010 (hidden, 2H, H-
14ꢂ), 1.993 (hidden, 2H, H-14+), 2.15–1.85 (m, 8H, H-14, H-140),
1.788 (br AB, 2H, H-13C), 1.735 (br AB, 2H, H-13ꢂ0), 1.649 (br d,
0
2
x
0
2H, J ¼ 14.4 Hz, H-13 ), 1.546 (m, 2H, H-140), 1.375 (s, 18H, H-
0
7E), 1.355 (s, 18H, H-7A), 1.200 (m, 2H, H-13C ), 0.860 (s, 18H, H-
7G), 0.816 (s, 18H, H-7C). MALDI-TOF MS m/z calcd for
[C144H184KN16O32Hf2]+: 3047.212 (average mass), found:
3047.194 (peak of maximum intensity).
Reaction of 1H4 with KCl followed by addition of Hf(acac)4. A
mixture of 1H4 (64.8 mg, 48.7 mmol) and KCl (1.82 mg, 24.4
mmol) in CH3OH (20 mL) was heated at reux for 4 h. Next
Hf(acac)4 (28 mg, 48.7 mmol) in CH3OH (5 mL) was added via
cannula to the reaction mixture, which was further heated at
reux for 18 h. The mixture became homogeneous aer 15 min
at 60 ꢂC. The solvent was evaporated, leaving a brown solid (90
mg). Analysis by 1H NMR and MALDI-TOF MS showed that this
residue was identical to the material obtained in the previous 10 (a) M. Lee, S.-J. Lee and L.-H. Jiang, J. Am. Chem. Soc., 2004,
experiment.
126, 12724; (b) F. Corbellini, A. Mulder, A. Sartori,
M. J. W. Ludden, A. Casnati, R. Ungaro, J. Huskens,
M. Crego-Calama and D. N. Reinhoudt, J. Am. Chem. Soc.,
2004, 126, 17050; (c) H. Huang, D. M. Li, W. Wang,
Y.-C. Chen, K. Khan, S. Song and Y.-S. Zheng, Org. Biomol.
Chem., 2012, 10, 729.
Acknowledgements
This work was supported by the Centre National de la Recher-
che Scientique (CNRS), the Conseil Regional de Bourgogne
´
(program PARI IME SMT8), and the Groupement National de 11 (a) R. Ludwig, H. Matsumoto, M. Takeshita, K. Ueda and
Recherche GNR PARIS. P.J. thanks the CNRS and the Conseil
S. Shinkai, Supramol. Chem., 1995, 4, 319; (b) L. Bennouna,
J. Vicens and Z. Asfari, J. Inclusion Phenom. Macrocyclic
Chem., 2001, 40, 96; (c) U. V. Trivedi, S. K. Menon and
Y. K. Agrawal, React. Funct. Polym., 2002, 50, 205; (d)
B. Boulet, C. Bouvier-Capely, C. Cossonnet and G. Cote,
Solvent Extr. Ion Exch., 2006, 24, 319; (e) L. Poriel,
B. Boulet, C. Cossonnet and C. Bouvier-Capely, Radiat.
Prot. Dosim., 2007, 127, 273; (f) B. Boulet, C. Bouvier-
Capely, G. Cote, L. Poriel and C. Cossonnet, J. Alloys
´
Regional de Bourgogne for
a
PhD fellowship (2009-
9201AAO037S03746).
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