Communications
1
3
9
1
1
1
1
1
2
4.29, 14.81, 17.26, 18.33, 18.36, 20.66, 22.89, 28.16, 28.20, 29.58, 29.59,
Zhang, O. S. Smart, G. A. Woolley, Biochemistry 2004, 43,
15329 –15338.
0.70, 32.09, 32.10, 32.39, 32.89, 34.42, 34.51, 90.57, 90.61, 90.76, 91.00,
1.35, 91.40, 119.02, 123.13, 123.19, 123.50, 123.83, 123.97, 124.00,
25.37, 127.57, 128.32, 128.55, 128.60, 128.86, 129.21, 129.33, 129.66,
29.72, 130.73, 131.59, 131.87, 131.89, 131.93, 131.98, 132.41, 132.47,
32.55, 133.24, 133.92, 134.92, 135.93, 135.98, 136.29, 136.37, 136.72,
37.08, 137.68, 138.31, 139.28, 140.03, 140.92, 141.72, 151.18, 152.28,
[7] M. J. Pandya, E. Cerasoli, A. Joseph, R. G. Stoneman, E. Waite,
D. N. Woolfson, J. Am. Chem. Soc. 2004, 126, 17016 –17024.
[8] a) J. R. Moran, S. Karbach, D. J. Cram, J. Am. Chem. Soc. 1982,
104, 5826 –5828; b) D. J. Cram, H.-J. Choi, J. A. Bryant, C. B.
Knobler, J. Am. Chem. Soc. 1992, 114, 7748 –7765.
[9] P. Soncini, S. Bonsignore, E. Dalcanale, F. Ugozzoli, J. Org.
Chem. 1992, 57, 4608 –4612.
[10] T. Haino, D. M. Rudkevich, A. Shivanyuk, K. Rissanen, J.
Rebek, Jr., Chem. Eur. J. 2000, 6, 3797 –3805.
[11] P. J. Skinner, A. G. Cheetham, A. Beeby, V. Gramlich, F.
Diederich, Helv. Chim. Acta 2001, 84, 2146 –2153.
[12] M. Frei, F. Marotti, F. Diederich, Chem. Commun. 2004, 1362 –
1363.
1
9
52.46, 153.31, 154.36, 159.08, 161.68 ppm; F NMR (CDCl3,
82.5 MHz): d = À134.5 (q, J = 33.5), À145.1 ppm (q, J = 32.5); IR
(neat): n˜ = 2957 (w), 2924 (m), 2855 (w), 1739 (s), 1524 (m), 1479 (m),
1
1
444 (m), 1411 (s), 1362 (s), 1326 (s), 1275 (m), 1231 (m), 1190 (s),
158 (s), 1116 (m), 1103 (m), 1083 (m), 1018 (m), 979 (m), 898 (m), 837
À1
(
(
m), 760 (m), 708 (m), 669 (w), 604 cm (w); UV/Vis (CHCl ): l
e) = 332 (184000), 529 (72000), 571 (21000), 619 nm (98000);
3
max
Fluorescence (CHCl , l = 490 nm): lmax = 542 nm, 630 nm; HR-
MALDI-MS
C188H156B F N O , calcd 2880.21599).
3
exc
+
(matrix:
3-HPA):
2880.2161
([MÀF] ,
[13] a) V. A. Azov, F. Diederich, Y. Lill, B. Hecht, Helv. Chim. Acta
2003, 86, 2149 –2155; b) V. A. Azov, P. J. Skinner, Y. Yamakoshi,
P. Seiler, V. Gramlich, F. Diederich, Helv. Chim. Acta 2003, 86,
3648 –3670.
þ
14 12
2
3
Received: March 16, 2005
[
14] P. P. Castro, G. Zhao, G. A. Masangkay, C. Hernandez, L. M.
Gutierrez-Tunstad, Org. Lett. 2004, 6, 333 –336.
Keywords: cavitands · conformation analysis · FRET
.
[15] a) J. Chen, A. Burghart, A. Derecskei-Kovacs, K. Burgess, J.
Org. Chem. 2000, 65, 2900 –2906; b) A. Burghart, H. Kim, M. B.
Welch, L. H. Thoresen, J. Reibenspies, K. Burgess, F. Bergström,
L. B.-. Johansson, J. Org. Chem. 1999, 64, 7813 –7819; c) J.
Karolin, L. B.-A. Johansson, L. Strandberg, T. Ny, J. Am. Chem.
Soc. 1994, 116, 7801 –7806.
16] a) T. Förster, Ann. Phys. 1948, 2, 55 –75; b) P. R. Selvin, Methods
Enzymol. 1995, 246, 300 –334.
17] AM1 calculations: Spartan 04 for Windows, Wavefunction Inc.,
(
fluorescence resonance energy transfer) · molecular devices
[
1] a) Special issue on molecular machines: Acc. Chem. Res. 2001,
4, 410 –522; b) Molecular Switches (Ed.: B. L. Feringa), Wiley-
3
VCH, Weinheim, 2001.
[
[
[
[
2] a) S. Kang, S. A. Vignon, H.-R. Tseng, J. F. Stoddart, Chem. Eur.
J. 2004, 10, 2555 –2564; b) H.-R. Tseng, S. A. Vignon, J. F.
Stoddart, Angew. Chem. 2003, 115, 1529 –1533; Angew. Chem.
Int. Ed. 2003, 42, 1491 –1495.
18401 Von Karman Ave., Irvine, CA 92612 USA, 2003.
18] J. A. Marsden, M. M. Haley in Metal-Catalyzed Cross-Coupling
Reactions, 2nd ed., Vol. 1 (Eds.: A. de Meijere, F. Diederich),
Wiley-VCH, Weinheim, 2004, pp. 317 –394.
[
[
3] G. Bottari, D. A. Leigh, E. M. PØrez, J. Am. Chem. Soc. 2003,
125, 13360 –13361.
4] a) M. C. Jimenez-Molero, C. Dietrich-Buchecker, J.-P. Sauvage,
Chem. Commun. 2003, 1613 –1616; b) M. C. Jimenez, C. Die-
trich-Buchecker, J.-P. Sauvage, Angew. Chem. 2000, 112, 3422 –
[
19] O. Lavastre, L. Ollivier, P. H. Dixneuf, S. Sibandhit, Tetrahedron
1996, 52, 5495 –5504.
[
20] For further details of the analysis of the contracted/expanded
conformations by NMR spectroscopy as well as for the kinetics
and thermodynamics of vase/kite switching, see: V. A. Azov, B.
Jaun, F. Diederich, Helv. Chim. Acta 2004, 87, 449 –462.
21] Ongoing studies in collaboration with Prof. B. Hecht (University
of Basel), see: a) S. Weiss, Science 1999, 283, 1676 –1683; b) B.
Hecht, B. Sick, U. P. Wild, V. Deckert, R. Zenobi, O. J. F. Martin,
D. W. Pohl, J. Chem. Phys. 2000, 112, 7761 –7774.
3425; Angew. Chem. Int. Ed. 2000, 39, 3284 –3287.
[
5] a) M. Barboiu, L. Prodi, M. Montalti, N. Zaccheroni, N.
Kyritsakas, J.-M. Lehn, Chem. Eur. J. 2004, 10, 2953 –2959;
b) M. Barboiu, G. Vaughan, N. Kyritsakas, J.-M. Lehn, Chem.
Eur. J. 2003, 9, 763 –769; c) M. Barboiu, J.-M. Lehn, Proc. Natl.
Acad. Sci. USA 2002, 99, 5201 –5206.
[
[
6] a) T. Lougheed, V. Borisenko, T. Hennig, K. Rück-Braun, G. A.
Woolley, Org. Biomol. Chem. 2004, 2, 2798 –2801; b) D. C.
Burns, D. G. Flint, J. R. Kumita, H. J. Feldman, L. Serrano, Z.
4
638
ꢀ 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2005, 44, 4635 –4638