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J.-Y. Shin et al. / Tetrahedron Letters 49 (2008) 5515–5518
120.13 (CH, 2C), 119.95 (CH), 116.98 (CH), 14.94 (CH3, 2C); ESIMS 334.2 m/z
([M+Na]+); elemental analysis (C17H1611BF2N3, %) found 13.66 (N), 65.85 (C),
5.50 (H), calcd 13.51 (N), 65.62 (C), 5.18 (H); UV–vis (CH2Cl2) kmax/nm (log
References and notes
e)
1. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier:
Amsterdam, 1989.
2. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH:
Weinheim, 1995.
3. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D.,
MacNicol, D. D., Vögtle, F., Lehn, J.-M., Eds.; Pergamon: Oxford, 1996.
4. Desiraju, G. R. Nature 2001, 412, 397.
338 (4.20), 512 (5.07). Crystal data for 10: C17H16N3F2B, T = 173 K, Mw = 311.14,
monoclinic, P21/n(#14), a = 7.4989(3) Å, b = 20.5912(8) Å, c = 9.7926(3) Å,
b = 98.401(1)°, V = 1495.86(10) Å3, Dc = 1.382 g cmꢀ3
,
Z = 4, R1 = 0.0402
(I > 2.00r(I)), wR2 = 0.112 (all data), GOF = 1.06. CCDC 683840.
16. Analytical data for compound 11 (mp = 155–167 °C) 1H NMR at rt (CD2Cl2,
300 MHz) d = 7.23 (t, J = 7.7, 1H), 6.85 (d, J = 7.7, 2H), 6.81 (d, J = 3.7, 2H), 6.79
(s, 1H), 6.29 (d, J = 4.0, 2H), 3.87 (s, 2H), 2.60 (s, 6H); 13C NMR at rt (acetone-d6,
100.64 MHz) d = 156.32, 134.98, 133.53, 130.94, 122.90, 119.58, 114.62,
5. Hollingsworth, M. D. Science 2002, 295, 2410.
6. MacDonald, J. C.; Dorrestein, P. C.; Pilley, M. M.; Foote, M. M.; Lundburg, J.
L.; Henning, R. W.; Schultz, A. J.; Manson, J. L. J. Am. Chem. Soc. 2000, 122,
11692.
7. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629.
8. Sommerdijk, N. A. J. M. Angew. Chem., Int. Ed. 2003, 42, 3572.
9. Chen, Q.; Dolphin, D. Can. J. Chem. 2002, 80, 1668.
10. Thompson, A.; Rettig, S. J.; Dolphin, D. Chem. Commun. 1999, 631.
11. Zhang, Y.; Thompson, A.; Rettig, S. J.; Dolphin, D. J. Am. Chem. Soc. 1998, 120,
13537.
120.48, 14.85; ESIMS 334.2 m/z ([M+Na]+); UV–vis (CH2Cl2) kmax/nm (log
e)
437 (4.04), 482 (4.31), 508 (4.84). Crystal data for 11: C17H16N3F2B, T = 173 K,
Mw = 311.14, monoclinic, P21/n(#14), a = 9.8037(5) Å, b = 23.8594(11) Å,
c = 13.3120(6) Å, b = 103.055(2)°, V = 3033.3(2) Å3, Dc = 1.363 g cmꢀ3
,
Z = 8,
R1 = 0.0447 (I > 2.00r(I)), wR2 = 0.118 (all data), GOF = 1.03. CCDC 683841.
17. Analytical data for compound 12 (mp = >230 °C) 1H NMR at rt (CD2Cl2, 300 MHz)
d = 7.67 (d, J = 8.3, 2H), 7.55 (d, J = 8.3, 2H), 7.49 (d, J = 8.5, 2H), 6.83 (d, J = 3.9,
2H), 6.78 (d, J = 8.5, 2H), 6.32 (d, J = 3.9, 2H), 3.88 (br s, 2H), 2.62 (s, 6H); 13C NMR
at rt (acetone-d6, 100.64 MHz) d = 158.26, 157.97, 149.86, 144.35, 143.57,
135.11, 133.31, 132.20, 132.10 (CH, 2C), 131.32 (CH, 2C), 128.65 (CH, 2C), 126.40
(CH, 2C), 120.38 (CH, 2C), 115.68 (CH, 2C), 14.95 (CH3, 2C); ESIMS 410.3 m/z
([M+Na]+); elemental analysis (C23H2011BF2N3, %) found 10.58 (N), 71.10 (C),
12. Shin, J.-Y.; Dolphin, D.; Patrick, B. O. Cryst. Growth Des. 2004, 4, 659.
13. Wagner, R. W.; Lindsey, J. S. Pure Appl. Chem. 1996, 68, 1373.
14. Analytical data for compound
9
(mp = 167–169 °C) 1H NMR at rt (CDCl3,
300 MHz) d = 7.54 (t, J = 8.3, 1H), 7.38 (dd, J = 7.6, ddJ = 1.4, 1H), 7.10 (t, J = 7.5,
1H), 7.04 (d, J = 8.2, 1H), 7.00 (d, J = 4.0, 2H), 6.52 (d, J = 4.1, 2H), 3.07 (br s, 2H),
2.93 (s, 6H); 13C NMR at rt (CD2Cl2, 100.64 MHz) d = 158.52, 145.30, 140.48,
135.06, 131.83 (CH), 131.11 (CH), 130.52 (CH, 2C), 120.05 (CH, 2C), 119.33,
118.08 (CH), 116.48 (CH), 15.23 (CH3, 2C); EIMS m/z (C17H1611BF2N3, m/z) found
5.60 (H), calcd 10.85 (N), 71.34 (C), 5.21 (H); UV–vis (CH2Cl2) kmax/nm (log e) 415
(4.54), 512 (5.34). Crystal data for 12: C23H20N3F2B, T = 173 K, Mw = 387.23,
monoclinic, P21/c(#14), a = 11.3809(14) Å, b = 13.251(2) Å, c = 12.5306(14) Å,
b = 92.778(4)°, V = 1887.5(4) Å3, Dc = 1.363 g cmꢀ3
,
Z = 4, R1 = 0.0431
(I > 2.00r(I)), wR2 = 0.109 (all data), GOF = 1.02. CCDC 683842.
311.14156, calcd 311.14053; UV–vis (CH2Cl2) kmax/nm (log e) 333 (4.00), 515
18. Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997,
119, 1599.
19. Pagano, R. E.; Martin, O. C.; Kang, H. C.; Haugland, R. P. J. Cell. Biol. 1991, 113,
1267.
20. Bricks, J. L.; Kovalchuk, A.; Trieflinger, C.; Nofz, M.; Büschel, M.; Tolmachev, A.
I.; Daub, J.; Rurack, K. J. Am. Chem. Soc. 2005, 127, 13522.
21. Costela, A.; Garc´ıa-Moreno, I.; Cómez, C.; Amat-Guerri, F.; Liras, M.; Sastre, R.
Appl. Phys. B 2003, 76, 365.
(4.95). Crystal data for 9: C17H16N3F2B, T = 173 K, Mw = 311.14, monoclinic, P21/
c(#14), a = 21.3685(13) Å, b = 9.6969(4) Å, c = 16.0314(9) Å, b = 110.662(3)°,
V = 3108.2(3) Å3, Dc = 1.330 g cmꢀ3
, Z = 8, R1 = 0.0494 (I > 2.00r(I)), wR2 =
0.141 (all data), GOF = 1.02. CCDC 683839.
15. Analytical data for compound 10 (mp = 225–227 °C) 1H NMR at rt (CD2Cl2,
300 MHz) d = 7.32 (t, J = 7.7, 1H), 6.75–6.91 (m, 4H), 6.82 (s, 1H), 6.29 (d, J = 4.1,
2H), 3.87, (br s, 2H), 2.60 (s, 6H); 13C NMR at rt (acetone-d6, 100.64 MHz)
d = 157.99, 149.50, 135.61, 135.23, 131.43 (CH, 2C), 129.89 (CH), 120.16 (CH),