5
6
7
A. P. de Silva and N. D. McClenaghan, Chem. Eur. J., 2004, 10,
574–586.
A. Credi, V. Balzani, S. J. Langford and J. F. Stoddart, J. Am. Chem.
Soc., 1997, 119, 2679–2681.
A. P. de Silva, H. Q. N. Gunaratne and C. P. McCoy, J. Am. Chem.
Soc., 1997, 119, 7891–7892.
8
9
D. Parker and J. A. Gareth Williams, Chem. Commun., 1998, 245–246.
A. P. de Silva, I. M. Dixon, H. Q. N. Gunaratne, T. Gunnlaugsson,
P. R. S. Maxwell and T. E. Rice, J. Am. Chem. Soc., 1999, 121,
1
393–1394.
0 A. Roque, F. Pina, S. Alves, R. Ballardini, M. Maestri and V. Balzani,
J. Mater. Chem., 1999, 9, 2265–2269.
1
11 F. Pina, M. J. Melo, M. Maestri, P. Passaniti and V. Balzani, J. Am.
Chem. Soc., 2000, 122, 4496–4498.
2 G. McSkimming, J. H. R. Tucker, H. Bouas-Laurent and
J.-P. Desvergne, Angew. Chem., Int. Ed., 2000, 39, 2167–2169.
1
1
1
3 H. T. Baytekin and E. U. Akkaya, Org. Lett., 2000, 2, 1725–1727.
4 T. Gunnlaugsson, D. A. Mac D o´ nail and D. Parker, Chem. Commun.,
000, 93–94.
5 T. Gunnlaugsson, D. A. Mac D o´ nail and D. Parker, J. Am. Chem. Soc.,
001, 123, 12866–12876.
2
1
2
Fig. 3 Normalised Tb(III) luminescence intensities of a 1:1 mixture with
2
16 S. Alves, F. Pina, M. T. Albelda, E. Garc ´ı a-Espa n˜ a, C. Soriano and
S. V. Luis, Eur. J. Inorg. Chem., 2001, 405–412.
1
(75 mM, MeCN) at lobs = 544 nm with different chemical inputs [Cl :
1
7 G. Bergamini, C. Saudan, P. Ceroni, M. Maestri, V. Balzani, M. Gorka,
S.-K. Lee, J. van Heyst and F. V o¨ gtle, J. Am. Chem. Soc., 2004, 126,
6466–16471.
8 M. de Sousa, M. Kluciar, S. Abad, M. A. Miranda, B. de Castro and
U. Pischel, Photochem. Photobiol. Sci., 2004, 3, 639–642.
1
50 mM; O : 1.9 mM (air-equilibrated); TEA: 75 mM]. The dashed line
2
marks the threshold. The insets show the logic table and the respective
1
symbolic representation of the EnNOR function.
1
1
9 J.-M. Montenegro, E. Perez-Inestrosa, D. Collado, Y. Vida and
We acknowledge financial support by the Funda c¸ a˜ o para a
Ci eˆ ncia e Tecnologia, Lisbon (Grant No. POCI/QUI/58535/2004
for U. P.). Further, we thank Dr C. Baleiz a˜ o (Instituto Superior
T e´ cnico, Lisbon, Portugal) for phosphorescence measurements
and Prof. W. M. Nau (International University Bremen,
Germany) for making his laser-flash-photolysis-setup available.
R. Suau, Org. Lett., 2004, 6, 2353–2355.
0 S. Banthia and A. Samanta, Eur. J. Org. Chem., 2005, 4967–4970.
2
21 N. Sabbatini, M. Guardigli and J. M. Lehn, Coord. Chem. Rev., 1993,
123, 201–228.
2
2 J. P. Cross, M. Lauz, P. D. Badger and S. Petoud, J. Am. Chem. Soc.,
004, 126, 16278–16279.
3 J. H. Barlow, R. S. Davidson, A. Lewis and D. R. Russell, J. Chem.
Soc., Perkin Trans. 2, 1979, 1103–1109.
2
2
24 J. D. Coyle, A. Harriman and G. L. Newport, J. Chem. Soc., Perkin
Trans. 2, 1979, 799–802.
Notes and references
{ The measurement of the phosphorescence spectrum of 1 at 77 K in
presence of 1 eq. Gd(III), whose energy levels are too high-lying to quench
25 V. Wintgens, P. Valat, J. Kossanyi, L. Biczok, A. Demeter and T. B e´ rces,
J. Chem. Soc., Faraday Trans., 1994, 90, 411–421.
26 H. G o¨ rner, A. G. Griesbeck, T. Heinrich, W. Kramer and
M. Oelgem o¨ ller, Chem. Eur. J., 2001, 7, 1530–1538.
21
via energy transfer, yielded a triplet energy of E
5
Fig, S5). The energy of the D
T
= 23 400 cm (ESI,{
level of Tb(III) was taken as 20 500 cm
21
4
(
§
cf. ref. 8).
The rate constant for electronic energy transfer (kEET) from phthalimide
(with tobs = 2.4 ms in
27 L. Alderighi, P. Gans, A. Ienco, D. Peters, A. Sabatini and A. Vacca,
Coord. Chem. Rev., 1999, 184, 311–318.
28 R. C. Howell, S. H. Edwards, A. S. Gajadhar-Plummer, I. A. Kahwa,
G. L. McPherson, J. T. Mague, A. J. P. White and D. J. Williams,
Molecules, 2003, 8, 565–592.
to Tb(III) was calculated with kEET = 1/tobs 2 1/t
presence of 1 eq. Tb(III) and t = 3.5 ms in presence of 1 eq. H ). The
bimolecular oxygen quenching constant (k
0
+
0
8
21 21
q
= 6.3 6 10 M
s ) of the
triplet state of 1 in presence of 1 eq. Tb(III) was determined via lifetime
measurements with laser-flash-photolysis (ESI,{ Fig. S6). The pseudo-
29 A. P. de Silva, H. Q. N. Gunaratne and T. E. Rice, Angew. Chem., Int.
Ed. Engl., 1996, 35, 2116–2118.
2
unimolecular rate constant was calculated with [O ] = 1.9 mM (air-
equilibrated MeCN solution).
30 M. Montalti, L. Prodi, N. Zaccheroni, L. Charbonni e` re, L. Douce and
R. Ziessel, J. Am. Chem. Soc., 2001, 123, 12694–12695.
3
1 L. J. Charbonni e` re, R. Ziessel, M. Montalti, L. Prodi, N. Zaccheroni,
C. Boehme and G. Wipff, J. Am. Chem. Soc., 2002, 124, 7779–7788.
32 T. Yamada, S. Shinoda and H. Tsukube, Chem. Commun., 2002,
1218–1219.
1
A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley,
C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97,
1515–1566.
F. M. Raymo, Adv. Mater., 2002, 14, 401–414.
V. Balzani, A. Credi and M. Venturi, ChemPhysChem, 2003, 4, 49–59.
G. J. Brown, A. P. de Silva and S. Pagliari, Chem. Commun., 2002,
2
3
4
33 S. W. Magennis, S. Parsons and Z. Pikramenou, Chem. Eur. J., 2002, 8,
5761–5771.
34 N. Chatterton, Y. Bretonni e` re, J. P e´ caut and M. Mazzanti, Angew.
Chem., Int. Ed., 2005, 44, 7595–7598.
2461–2463.
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