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4. (a) Lim, C. W.; Hong, J.-I. Tetrahedron Lett. 2000, 41, 3113. (b) Ahn, D.-R.; Kim, T. W.; Hong, J.-I. Tetrahedron
Lett. 1999, 40, 6045. (c) Haino, T.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 11253. (d)
Hayashida, O.; Kato, M.; Akagi, K.; Ayoyama, A. J. Am. Chem. Soc. 1999, 121, 11597. (e) Pellet-Rostaing, S.;
Nicod, L.; Chitry, F.; Lemaire, M. Tetrahedron Lett. 1999, 40, 8793. (f) Mezo, A. R.; Sherman, J. C. J. Org.
Chem. 1998, 63, 6824. (g) Gansey, M. H. B. G.; Bakker, F. K. G.; Feiters, M. C.; Geurts, H. P. M.; Verboom,
W.; Reinhoudt, D. N. Tetrahedron Lett. 1998, 39, 5447. (h) Lippmann, T.; Wilde, H.; Pink, M.; Schafer, A.;
Hesse, M.; Mann, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1195. (i) Schneider, H.-J.; Gu¨ttes, D.; Schneider, U.
J. Am. Chem. Soc. 1988, 110, 6449. (j) Schneider, H.-J.; Gu¨ttes, D.; Schneider, U. Angew. Chem., Int. Ed. Engl.
1986, 25, 647.
5. Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, 1994.
1
6. Selected spectral data for 2: H NMR (300 MHz, CDCl3) l 8.29 (s, 4H, ArH), 7.80 (s, 8H, ArH), 7.45 (s, 4H,
ArH), 5.85 (d, J=7.13 Hz, 4H, ArOCHoutHinOAr), 5.13 (q, J=7.36 Hz, 4H, CHCH3), 5.01 (s, 8H, ArCH2O),
4.63 (d, J=7.13 Hz, 4H, ArOCHoutHinOAr), 3.87 (s, 24H, ArCO2CH3), 1.86 (d, J=7.35 Hz, 12H, CHCH3); 13C
NMR (75 MHz, CDCl3) l 165.9, 158.6, 153.9, 139.1, 132.0, 123.5, 122.0, 120.9, 120.0, 99.8, 61.3, 52.3, 31.2, 16.1;
ESI-MS m/z 1480 (M+). Selected spectral data for 3: 1H NMR (300 MHz, DMSO-d6) l 13.08 (bs, 8H,
ArCOOH), 8.06 (s, 4H, ArH), 7.92 (s, 4H, ArH), 7.66 (s, 8H, ArH), 5.89 (d, J=7.50 Hz, 4H,
ArOCHoutHinOAr), 4.91 (m, 12H, ArCH2O+CHCH3), 4.47 (d, J=7.59 Hz, 4H, ArOCHoutHinOAr), 1.91 (d,
J=7.31 Hz, 12H, CHCH3); 13C NMR (75 MHz, DMSO-d6) l 166.4, 158.6, 153.2, 139.1, 132.7, 122.6, 122.2,
1
119.3, 99.6, 60.9, 31.3, 16.1; FAB−-MS (NBA) m/z 1367 (M−H)−. Selected spectral data for 4: H NMR (300
MHz, D2O) l 7.83 (s, 4H, ArH), 7.65 (s, 8H, ArH), 7.48 (s, 4H, ArH), 5.92 (d, J=7.27 Hz, 4H,
ArOCHoutHinOAr), 4.96 (s, 8H, ArCH2O), 4.94 (q, J=7.40 Hz, 4H, CHCH3), 4.35 (d, J=7.30 Hz, 4H,
ArOCHoutHinOAr), 1.79 (d, J=7.39 Hz, 12H, CHCH3); 13C NMR (75 MHz, D2O) l 175.0, 158.1, 153.6, 139.9,
138.4, 122.8, 122.2, 118.5, 100.6, 61.6, 31.8, 15.7.
7. (a) Kim, K.; Peak, K. Bull. Korean Chem. Soc. 1993, 14, 658. (b) Sorrel, T. N.; Pigge, F. C. J. Org. Chem. 1993,
58, 784.
1
8. We checked the concentration-dependent H NMR chemical shifts from 0.2 to 10 mM.
9. A reference host molecule (7) was prepared using Mitsunobu coupling as a key step.
Reagents and conditions. (i) MeI, K2CO3; (ii) LiAlH4, reflux; (iii) 5-hydroxy-dimethylisophthalate, PPh3, DEAD;
(iv) NaOH, THF/MeOH/H2O, rt, HCl (1N); (v) NaOH.
Selected spectral data for 5: 1H NMR (300 MHz, CDCl3) l 8.27 (s, 1H, ArH), 7.93 (s, 2H, ArH), 7.31 (t, J=8.40
Hz, 1H, ArH), 6.60 (d, J=8.38 Hz, 2H, ArH), 5.25 (s, 2H, ArCH2OAr), 3.94 (s, 6H, ArCO2CH3), 3.85 (s, 6H,
ArOCH3); 13C NMR (75 MHz, CDCl3) l 166.3, 159.4, 159.3, 131.4, 130.5, 122.6, 120.5, 112.0, 103.7, 59.9, 55.8,
52.3; EI-MS m/z 360 (M+). Selected spectral data for 6: 1H NMR (300 MHz, DMSO-d6) l 13.27 (s, 2H,
ArCO2H), 8.05 (s, 1H, ArH), 7.71 (s, 2H, ArH), 7.35 (t, J=8.38 Hz, 1H, ArH), 6.71 (d, J=8.40 Hz, 2H, ArH),
5.12 (s, 2H, ArCH2OAr), 3.80 (s, 6H, ArOCH3); 13C NMR (75 MHz, DMSO-d6) l 166.5, 159.0, 158.9, 132.6,
1
130.9, 122.1, 119.3, 111.3, 104.0, 59.4, 55.9; EI-MS m/z 332.0904 (M+). Selected spectral data for 7: H NMR
(300 MHz, D2O) l 7.78 (s, 1H, ArH), 7.49 (s, 2H, ArH), 7.26 (t, J=8.43 Hz, 1H, ArH), 6.61 (d, J=8.46 Hz,
2H, ArH), 5.11 (s, 2H, ArCH2OAr), 3.70 (s, 6H, ArOCH3); 13C NMR (75 MHz, D2O) l 175.0, 159.2, 158.1,
138.3, 131.7, 122.5, 118.5, 112.0, 105.0, 60.5, 56.3.
10. Hucho, F. Neurotransmitter Receptors; Elsevier: Amsterdam, The Netherlands, 1993.
11. Rekharsky, M.; Inoue, Y. J. Am. Chem. Soc. 2000, 122, 4418–4435.
12. Mizutani, T.; Wada, K.; Kitagawa, S. J. Am. Chem. Soc. 1999, 121, 11425–11431.
.