Synthesis and fluorescence ion-sensory properties of the first dehydropyridoannulene-type cyclophane with enforced exotopic metal ion binding sites

Chemistry - A European Journal

Volumn 9, Issue 11, 2003, Pages 2531-2541

  Baxter, Paul N W ^a,b  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b INSTITUT CHARLES SADRON   (France)

Author keywords

Alkynes; Cyclooligomerization; Cyclophanes; Macrocyclic ligands; Sensors

Indexed keywords

CONFORMATIONS; FLUORESCENCE; GROUND STATE; PRECIPITATION (CHEMICAL); QUENCHING; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

ION-SENSORY PROPERTIES;

COMPLEXATION;

[BENZENE 1,4 BIS(2,1 ETHYNEDIYL)]BIS[3 (4 TRIMETHYLSILYLETHYNYLPYRIDINE)]; ANNULENE DERIVATIVE; COBALT; CYCLOPHANE DERIVATIVE; DEHYDROPYRIDOANNULENE CYCLOPHANE; IRON; MACROCYCLIC COMPOUND; METAL ION; NICKEL; SILVER; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CALCULATION; CHEMICAL BINDING; CHEMICAL COMPOSITION; COMPLEX FORMATION; ELECTROMAGNETIC FIELD; FLUORESCENCE; POLYMERIZATION; PRECIPITATION; REACTION ANALYSIS; SPECTROSCOPY; SYNTHESIS; THEORY;

EID: 0037974645     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.2003044561     Document Type: Article

References (113)

1. For an informative series of reviews covering the field up to 1999, see: Top. Curr. Chem. 1999, 201, whole volume.
2. a) P. Ruggli, Justus Liebigs Ann. Chem. 1916, 412, 1;
3. b) P. Ruggli, Justus Liebigs Ann. Chem. 1913, 399, 174;
4. c) P. Ruggli, Justus Liebigs Ann. Chem. 1912, 392, 92.
5. Top. Curr. Chem. 1999, 199, whole volume.
6. a) Y. Tobe, H. Nakanishi, M. Sonoda, T. Wakahayashi, Y. Achiba, Chem. Commun. 1999, 1625;
7. b) Y. Tobe, N. Nakagawa, K. Naemura, T. Wakabayashi, T. Shida, Y. Achiba, J. Am. Chem. Soc. 1998, 120, 4544;
8. c) Y. Rubin, T. C. Parker, S. J. Pastor, S. Jalisatgi, C. Boulle, C. L. Wilkins, Angew. Chem. 1998, 110, 1353; Angew. Chem. Int. Ed. 1998, 37, 1226;
9. c) Y. Rubin, T. C. Parker, S. J. Pastor, S. Jalisatgi, C. Boulle, C. L. Wilkins, Angew. Chem. 1998, 110, 1353; Angew. Chem. Int. Ed. 1998, 37, 1226;
10. d) Y. Rubin, Chem. Eur. J. 1997, 3, 1009, and references therein.
11. R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052.
12. a) U. H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev. 1999, 28, 107;
13. b) F. Diederich, Nature 1994, 369, 199;
14. c) U. H. F. Bunz, Angew. Chem. 1994, 106, 1127; Angew. Chem. Int. Ed. Engl. 1994, 33, 1073;
15. c) U. H. F. Bunz, Angew. Chem. 1994, 106, 1127; Angew. Chem. Int. Ed. Engl. 1994, 33, 1073;
16. d) F. Diederich, Y. Rubin, Angew. Chem. 1992, 104, 1123; Angew. Chem. Int. Ed. Engl. 1992, 31, 1101.
17. d) F. Diederich, Y. Rubin, Angew. Chem. 1992, 104, 1123; Angew. Chem. Int. Ed. Engl. 1992, 31, 1101.
18. a) E. Mena-Osteritz, P. Bäuerle, Adv. Mater. 2001, 13, 243;
19. b) J. S. Moore, Acc. Chem. Res. 1997, 30, 402.
20. a) S. Eisler, R. R. Tykwinski, Angew. Chem. 1999, 111, 2138; Angew. Chem. Int. Ed. Engl. 1999, 38, 1940;
21. a) S. Eisler, R. R. Tykwinski, Angew. Chem. 1999, 111, 2138; Angew. Chem. Int. Ed. Engl. 1999, 38, 1940;
22. b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 492; Angew. Chem. Int. Ed. Engl. 1994, 33, 468.
23. b) A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 492; Angew. Chem. Int. Ed. Engl. 1994, 33, 468.
24. a) L. T. Scott, M. J. Cooney, C. Otte, C. Puls, T. Haumanm, R. Boese, P. J. Carroll, A. B. Smith III, A. de Meijere, J. Am. Chem. Soc. 1994, 116, 10275;
25. b) L. T. Scott, G. J. DeCicco, J. L. Hyun, G. Reinhardt, J. Am. Chem. Soc. 1985, 107, 6546. It may be noted that the name "pericyclynes" used in the latter two references has been replaced by the name "pericyclines" in the review of reference [1].
26. a) A. de Meijere, S. Kozhushkov, T. Haumann, R. Boese, C. Puls, M. J. Cooney, L. T. Scott, Chem. Eur. J. 1995, 1, 124;
27. b) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl. 1994, 33, 869.
28. b) A. de Meijere, S. Kozhushkov, C. Puls, T. Haumann, R. Boese, M. J. Cooney, L. T. Scott, Angew. Chem. 1994, 106, 934; Angew. Chem. Int. Ed. Engl. 1994, 33, 869.
29. a) R. H. Mitchell, Isr. J. Chem. 1980, 20, 294;
30. b) P. J. Garratt in Comprehensive Organic Chemistry; The Synthesis and Reactions of Organic Compounds, Vol. I (Ed.: J. F. Stoddart), Pergamon, Oxford, 1979, Chapter 2.6, p.361;
31. c) H. Meier, Synthsis 1972, 235.
32. a) J. M. Kehoc, J. H. Kiley, J. J. English, C. A. Johnson, R. C. Petersen, M. M. Haley, Org. Lett. 2000, 2, 969;
33. b) W. J. Youngs, C. A. Tessier, J. D. Bradshaw, Chem. Rev. 1999, 99, 3153;
34. c) J. J. Pak, T. J. R. Weakley, M. M. Haley, J. Am. Chem. Soc 1999, 121, 8182;
35. d) M. M. Haley, Synlett 1998, 557.
36. a) K. Campbell, C. J. Kuehl, M. J. Ferguson, P. J. Stang, R. R. Tykwinski, J. Am. Chem. Soc. 2002, 124, 7266;
37. b) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591.
38. J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 2655.
39. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
40. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
41. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
42. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
43. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
44. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
45. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
46. For the syntheses of dehydrotetrabenzoannulenes and related structures, see: a) M. L. Bell, R. Chiechi, C. A. Johnson, D. B. Kimball, A. J. Matzger, W. Brad Wan, T. J. R. Weakley, M. M. Haley, Tetrahedron 2001, 57, 3507; b) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Lett. 2000, 2, 3189; c) S. K. Collins, G. P. A. Yap, A. G. Fallis, Org. Angew. Chem. 2000, 112, 393; Angew. Chem. Int. Ed. 2000, 39, 385; d) M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson, T. J. R. Weakley, J. Am. Chem. Soc. 1997, 119, 2956; e) K. P. Baldwin, R. S. Simons, J. Rose, P. Zimmerman, D. M. Hercules, C. A. Tessier, W. J. Youngs, J. Chem. Soc. Chem. Commun. 1994, 1257. f) See reference [12b]. For the syntheses of dehydrotetrathiophenoannulene-type cyclophanes, see: g) M. J. Marsella, Z.-Q. Wang, R. J. Reid, K. Yoon, Org. Lett. 2001, 3, 885.
47. a) P. N. W. Baxter, Chem. Eur. J. 2002, 8, 5250;
48. b) P. N. W. Baxter, J. Org. Chem. 2001, 66, 4170.
49. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
50. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
51. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
52. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
53. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
54. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
55. For examples of ethynyl macrocycles that externally bind metal ions, see; a) O. Henze, D. Lentz, A. Schäfer, P. Franke, A. D. Schlüter, Chem. Eur. J. 2002, 8, 357. b) See reference [13a]; c) R. Gibe, J. R. Green, Chem. Commun. 2002, 1550; d) M. Laskoski, W. Steffen, J. G. M. Morton, M. D. Smith, U. H. F. Bunz, Angew. Chem. 2002, 114, 2484; Angew. Chem. Int. Ed. 2002, 41, 2378; e) K. Campbell, R. McDonald, N. R. Branda, R. R. Tykwinski, Org. Lett. 2001, 3, 1045. f) See reference [12b].
56. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
57. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
58. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
59. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
60. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
61. Pyridine-type ligands connected to/or within electronically delocalised organic scaffolds have been infrequently used for the sensing of metal ions. See for example: a) references [16a-b]; b) P. N. W. Baxter, J. Org. Chem. 2000, 65, 1257; c) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537; d) C.-S. Choi, T. Mutai, S. Arita, K. Araki, J. Chem. Soc. Perkin Trans. 2 2000, 243; e) M. Kimura, T. Horai, K. Hanabusa, H. Shirai, Adv. Mater. 1998, 10, 459; f) B. Wang, M. R. Wasielewski, J. Am. Chem. Soc. 1997, 119, 12.
62. The term "twistophane" is used to describe ethynyl cyclophanes that are completely ortho-conjugated, yet helically twisted and therefore non-planar chiral structures. Cyclic organic scaffolds satisfying the latter criteria comprise dehydrotetraarylannulenes, dehydrotetraarylannulene-type cyclophanes and higher homologues. Such materials constitute a small but slowly emergent subclass of conjugated ethynyl macrocycles of which 1-4 are the first reported examples with integrated heterocyclic N-donor sites for metal ion coordination.
63. The thermal-cyclisation reactions of ortho-diethynyl pyridines have been the subject of investigation, but reports on the synthesis of such materials remain rare. See: a) C.-S. Kim, K. C. Russell, J. Org. Chem. 1998, 63, 8229; b) K. J. Gibson, M. d'Alarcao, N. J. Leonard, J. Org. Chem. 1985, 50, 2462.
64. The thermal-cyclisation reactions of ortho-diethynyl pyridines have been the subject of investigation, but reports on the synthesis of such materials remain rare. See: a) C.-S. Kim, K. C. Russell, J. Org. Chem. 1998, 63, 8229; b) K. J. Gibson, M. d'Alarcao, N. J. Leonard, J. Org. Chem. 1985, 50, 2462.
65. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
66. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
67. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
68. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
69. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
70. + and NADH-type macrocyclic catalysts, see: a) Y. Kuroda, H. Seshimo, T. Kondo, M. Shiba, H. Ogoshi, Tetrahedron Lett. 1997, 38, 3939; b) A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. Werumeus Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981, and references therein. For cyclic peptide analogues with potential biological activity, see: c) A. El-Hamid Attia, M. H. Abo-Ghaga, O. I. Abd El-Salam, Collect. Czech. Chem. Commun. 1994, 59, 1451; for amide catenanes, see: d) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. 1995, 107, 1327; Angew. Chem. Int. Ed. Engl. 1995, 34, 1212; for metal ion-directed auto-assembly of cavitand architectures, see: e) L. Pirondini, D. Bonifazi, E. Menozzi, E. Wegelius, K. Rissanen, C. Massera, E. Dalcanale, Eur. J. Org. Chem. 2001, 2311.
71. a) T. Talik, Z. Talik, Roczniki Chem. 1962, 36, 539;
72. b) T. Talik, Roczniki Chem. 1962, 36, 1049;
73. c) T. Imahori, M. Uchiyama, T. Sakamoto, Y. Kondo, Chem. Commun. 2001, 2450.
74. A. Numata, Y. Kondo, T. Sakamoto, Synthesis 1999, 2, 306.
75. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467.
76. a) See reference [24]
77. b) A. Pelter, D. E. Jones, J. Chem. Soc. Perkin Trans. I 2000, 2289.
78. 4] compared to CuCl, as the former copper salt has a lower number of available sites for additional ligand attachment.
79. 4] and the 4 as it was generated.
80. For an example of the use of semi-empirical AM1 calculations for successfully predicting the conformations of ethynyl macrocycles, see: a) M. Srinivasan, S. Sankararaman, H. Hopf, I. Dix, P. G. Jones, J. Org. Chem. 2001, 66, 4299. b) Retrieved from the CCSD.
81. For an example of the use of semi-empirical AM1 calculations for successfully predicting the conformations of ethynyl macrocycles, see: a) M. Srinivasan, S. Sankararaman, H. Hopf, I. Dix, P. G. Jones, J. Org. Chem. 2001, 66, 4299. b) Retrieved from the CCSD.
82. t triflates used were ≥ 99.9% purity.
83. 3); R. G. Salomon, J. K. Kochi, J. Am. Chem. Soc. 1973, 95, 3300.
84. Proton-controllable fluorescence phenomena have been reported for linear, branched and cyclic conjugated organic scaffolds incorporating nitrogen-donor heterocycles, see: a) reference [16a]; b) R. E. Martin. J. A. Wytko, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1999, 82, 1470; c) G. R. Pabst, O. C. Pfüller, J. Sauer, Tetrahedron 1999, 55, 5047; d) T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 1996, 118, 3930. Macrocycle 4 and related structures are thus promising candidates for the construction of proton switches, transducers and conductors, as well as pH responsive NLO and electroluminescent materials.
85. Proton-controllable fluorescence phenomena have been reported for linear, branched and cyclic conjugated organic scaffolds incorporating nitrogen-donor heterocycles, see: a) reference [16a]; b) R. E. Martin. J. A. Wytko, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1999, 82, 1470; c) G. R. Pabst, O. C. Pfüller, J. Sauer, Tetrahedron 1999, 55, 5047; d) T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 1996, 118, 3930. Macrocycle 4 and related structures are thus promising candidates for the construction of proton switches, transducers and conductors, as well as pH responsive NLO and electroluminescent materials.
86. Proton-controllable fluorescence phenomena have been reported for linear, branched and cyclic conjugated organic scaffolds incorporating nitrogen-donor heterocycles, see: a) reference [16a]; b) R. E. Martin. J. A. Wytko, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1999, 82, 1470; c) G. R. Pabst, O. C. Pfüller, J. Sauer, Tetrahedron 1999, 55, 5047; d) T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 1996, 118, 3930. Macrocycle 4 and related structures are thus promising candidates for the construction of proton switches, transducers and conductors, as well as pH responsive NLO and electroluminescent materials.
87. Proton-controllable fluorescence phenomena have been reported for linear, branched and cyclic conjugated organic scaffolds incorporating nitrogen-donor heterocycles, see: a) reference [16a]; b) R. E. Martin. J. A. Wytko, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1999, 82, 1470; c) G. R. Pabst, O. C. Pfüller, J. Sauer, Tetrahedron 1999, 55, 5047; d) T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, T. Kanbara, J. Am. Chem. Soc. 1996, 118, 3930. Macrocycle 4 and related structures are thus promising candidates for the construction of proton switches, transducers and conductors, as well as pH responsive NLO and electroluminescent materials.
88. III ions in dilute solution is currently unclear. It may however be related to the presence of the relatively electron-donating trimethylsilylethynyl groups in 11, which would be expected to increase the basicity of the pyridine nitrogen lone pair electrons, thereby facilitating coordination to more highly charged metal ions.
89. II ions both by a colourimetric response and precipitation, see; O. Brümmer, J. J. La Clair, K. D. Janda, Org. Lett. 1999, 1, 415.
90. II, reflects the simple coordination environment, normally preferred by these two metals. This suggests that conjugated ligand structures based on 4 and 11 may serve as a new, lead class of sensory materials for metal ions with low coordination number preferences.
91. II will continue to evoke considerable interest. For recent examples of fluorescence chemosensors for mercury, see: a) L. Prodi, C. Bargossi, M. Montalti, N. Zaccheroni, N. Su, J. S. Bradshaw, R. M. Izatt, P. B. Savage, J. Am. Chem. Soc. 2000, 122, 6769; b) Y. Shen, B. P. Sullivan, J. Chem. Ed. 1997, 74, 685; c) reference [18f].
92. II will continue to evoke considerable interest. For recent examples of fluorescence chemosensors for mercury, see: a) L. Prodi, C. Bargossi, M. Montalti, N. Zaccheroni, N. Su, J. S. Bradshaw, R. M. Izatt, P. B. Savage, J. Am. Chem. Soc. 2000, 122, 6769; b) Y. Shen, B. P. Sullivan, J. Chem. Ed. 1997, 74, 685; c) reference [18f].
93. II will continue to evoke considerable interest. For recent examples of fluorescence chemosensors for mercury, see: a) L. Prodi, C. Bargossi, M. Montalti, N. Zaccheroni, N. Su, J. S. Bradshaw, R. M. Izatt, P. B. Savage, J. Am. Chem. Soc. 2000, 122, 6769; b) Y. Shen, B. P. Sullivan, J. Chem. Ed. 1997, 74, 685; c) reference [18f].
94. For the specific use of linear, ethynylpyridine-type ligands in the generation of coordination polymers, see: a) Md. B. Zaman, M. D. Smith, H.-Conrad zur Loye, Chem. Commun. 2001, 2256; b) J. E. Fiscus, S. Shotwell, R. C. Layland, M. D. Smith, H.-Conrad zur Loye, U. H. F. Bunz, Chem. Commun. 2001, 2674; c) A. Jouaiti, V. Jullien, M. Wais Hosseini, J.-M. Planeix, A. De Cian, Chem. Commun. 2001, 1114; d) M. Maekawa, H. Konaka, Y. Suenaga, T. Kuroda-Sowa, M. Munakata, J. Chem. Soc. Dalton Trans. 2000, 4160; e) A. J. Blake, N. R. Champness, A. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schröder, Chem. Commun. 1997, 2027.
95. For the specific use of linear, ethynylpyridine-type ligands in the generation of coordination polymers, see: a) Md. B. Zaman, M. D. Smith, H.-Conrad zur Loye, Chem. Commun. 2001, 2256; b) J. E. Fiscus, S. Shotwell, R. C. Layland, M. D. Smith, H.-Conrad zur Loye, U. H. F. Bunz, Chem. Commun. 2001, 2674; c) A. Jouaiti, V. Jullien, M. Wais Hosseini, J.-M. Planeix, A. De Cian, Chem. Commun. 2001, 1114; d) M. Maekawa, H. Konaka, Y. Suenaga, T. Kuroda-Sowa, M. Munakata, J. Chem. Soc. Dalton Trans. 2000, 4160; e) A. J. Blake, N. R. Champness, A. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schröder, Chem. Commun. 1997, 2027.
96. For the specific use of linear, ethynylpyridine-type ligands in the generation of coordination polymers, see: a) Md. B. Zaman, M. D. Smith, H.-Conrad zur Loye, Chem. Commun. 2001, 2256; b) J. E. Fiscus, S. Shotwell, R. C. Layland, M. D. Smith, H.-Conrad zur Loye, U. H. F. Bunz, Chem. Commun. 2001, 2674; c) A. Jouaiti, V. Jullien, M. Wais Hosseini, J.-M. Planeix, A. De Cian, Chem. Commun. 2001, 1114; d) M. Maekawa, H. Konaka, Y. Suenaga, T. Kuroda-Sowa, M. Munakata, J. Chem. Soc. Dalton Trans. 2000, 4160; e) A. J. Blake, N. R. Champness, A. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schröder, Chem. Commun. 1997, 2027.
97. For the specific use of linear, ethynylpyridine-type ligands in the generation of coordination polymers, see: a) Md. B. Zaman, M. D. Smith, H.-Conrad zur Loye, Chem. Commun. 2001, 2256; b) J. E. Fiscus, S. Shotwell, R. C. Layland, M. D. Smith, H.-Conrad zur Loye, U. H. F. Bunz, Chem. Commun. 2001, 2674; c) A. Jouaiti, V. Jullien, M. Wais Hosseini, J.-M. Planeix, A. De Cian, Chem. Commun. 2001, 1114; d) M. Maekawa, H. Konaka, Y. Suenaga, T. Kuroda-Sowa, M. Munakata, J. Chem. Soc. Dalton Trans. 2000, 4160; e) A. J. Blake, N. R. Champness, A. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schröder, Chem. Commun. 1997, 2027.
98. For the specific use of linear, ethynylpyridine-type ligands in the generation of coordination polymers, see: a) Md. B. Zaman, M. D. Smith, H.-Conrad zur Loye, Chem. Commun. 2001, 2256; b) J. E. Fiscus, S. Shotwell, R. C. Layland, M. D. Smith, H.-Conrad zur Loye, U. H. F. Bunz, Chem. Commun. 2001, 2674; c) A. Jouaiti, V. Jullien, M. Wais Hosseini, J.-M. Planeix, A. De Cian, Chem. Commun. 2001, 1114; d) M. Maekawa, H. Konaka, Y. Suenaga, T. Kuroda-Sowa, M. Munakata, J. Chem. Soc. Dalton Trans. 2000, 4160; e) A. J. Blake, N. R. Champness, A. Khlobystov, D. A. Lemenovskii, W.-S. Li, M. Schröder, Chem. Commun. 1997, 2027.
99. For a recent review on fluorescence molecular sensors for cation recognition, see: B. Valeur, I. Leray, Coord. Chem. Revs. 2000, 205, 3.
100. For recent reviews on the metal ion directed approach to crystal engineering of coordination networks and hybrid frameworks, see: a) G. Férey, Chem. Mater. 2001, 13, 3084; b) M. Wais Hosseini, in Crystal Engineering: From Molecules and Crystals to Materials, (Eds.: D. Braga, F. Grepioni, G. A. Orpen), Kluwer, 1999, pp.181-208. Macrocycle 4 and related structures may also potentially serve as tectons for the assembly of hydrogen-bonded polymers, zeolites and crystals. For the crystal engineering of 1D H-bonded polymers with ethynylpyridines, see: c) M. Ohkita, T. Suzuki, K. Nakatani, T. Tsuji, Chem. Commun. 2001, 1454. For recent reviews on the design of organic solids through hydrogen-bond assembly, see: d) Structure and Bonding (Vol. Ed.: M. Fujita), 2000, 96, pp. 2-146; e) Top. Curr. Chem. 1998, 198, whole volume.
101. For recent reviews on the metal ion directed approach to crystal engineering of coordination networks and hybrid frameworks, see: a) G. Férey, Chem. Mater. 2001, 13, 3084; b) M. Wais Hosseini, in Crystal Engineering: From Molecules and Crystals to Materials, (Eds.: D. Braga, F. Grepioni, G. A. Orpen), Kluwer, 1999, pp.181-208. Macrocycle 4 and related structures may also potentially serve as tectons for the assembly of hydrogen-bonded polymers, zeolites and crystals. For the crystal engineering of 1D H-bonded polymers with ethynylpyridines, see: c) M. Ohkita, T. Suzuki, K. Nakatani, T. Tsuji, Chem. Commun. 2001, 1454. For recent reviews on the design of organic solids through hydrogen-bond assembly, see: d) Structure and Bonding (Vol. Ed.: M. Fujita), 2000, 96, pp. 2-146; e) Top. Curr. Chem. 1998, 198, whole volume.
102. For recent reviews on the metal ion directed approach to crystal engineering of coordination networks and hybrid frameworks, see: a) G. Férey, Chem. Mater. 2001, 13, 3084; b) M. Wais Hosseini, in Crystal Engineering: From Molecules and Crystals to Materials, (Eds.: D. Braga, F. Grepioni, G. A. Orpen), Kluwer, 1999, pp.181-208. Macrocycle 4 and related structures may also potentially serve as tectons for the assembly of hydrogen-bonded polymers, zeolites and crystals. For the crystal engineering of 1D H-bonded polymers with ethynylpyridines, see: c) M. Ohkita, T. Suzuki, K. Nakatani, T. Tsuji, Chem. Commun. 2001, 1454. For recent reviews on the design of organic solids through hydrogen-bond assembly, see: d) Structure and Bonding (Vol. Ed.: M. Fujita), 2000, 96, pp. 2-146; e) Top. Curr. Chem. 1998, 198, whole volume.
103. For recent reviews on the metal ion directed approach to crystal engineering of coordination networks and hybrid frameworks, see: a) G. Férey, Chem. Mater. 2001, 13, 3084; b) M. Wais Hosseini, in Crystal Engineering: From Molecules and Crystals to Materials, (Eds.: D. Braga, F. Grepioni, G. A. Orpen), Kluwer, 1999, pp.181-208. Macrocycle 4 and related structures may also potentially serve as tectons for the assembly of hydrogen-bonded polymers, zeolites and crystals. For the crystal engineering of 1D H-bonded polymers with ethynylpyridines, see: c) M. Ohkita, T. Suzuki, K. Nakatani, T. Tsuji, Chem. Commun. 2001, 1454. For recent reviews on the design of organic solids through hydrogen-bond assembly, see: d) Structure and Bonding (Vol. Ed.: M. Fujita), 2000, 96, pp. 2-146; e) Top. Curr. Chem. 1998, 198, whole volume.
104. For recent reviews on the metal ion directed approach to crystal engineering of coordination networks and hybrid frameworks, see: a) G. Férey, Chem. Mater. 2001, 13, 3084; b) M. Wais Hosseini, in Crystal Engineering: From Molecules and Crystals to Materials, (Eds.: D. Braga, F. Grepioni, G. A. Orpen), Kluwer, 1999, pp.181-208. Macrocycle 4 and related structures may also potentially serve as tectons for the assembly of hydrogen-bonded polymers, zeolites and crystals. For the crystal engineering of 1D H-bonded polymers with ethynylpyridines, see: c) M. Ohkita, T. Suzuki, K. Nakatani, T. Tsuji, Chem. Commun. 2001, 1454. For recent reviews on the design of organic solids through hydrogen-bond assembly, see: d) Structure and Bonding (Vol. Ed.: M. Fujita), 2000, 96, pp. 2-146; e) Top. Curr. Chem. 1998, 198, whole volume.
105. For investigations into the potential use of multimetallic ethynylpyridyl scaffolds as molecular wires and multicentre magnetic materials, see: a) J. T. Lin, S.-S. Sun, J. J. Wu, L. Lee, K.-J. Lin, Y. F. Huang, Inorg. Chem. 1995, 34, 2323; b) A. J. Amoroso, A. M. W. Cargill Thompson, J. P. Maher, J. A. McCleverty, M. D. Ward, Inorg. Chem. 1995, 34, 4828. For the design of organic NLO materials with ethynylpyridines, see: c) reference [38c]. For a review on metalcoordinated conjugated pyridine ligands as NLO materials, see: d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229. For the synthesis of linear ethynylpyridine-type metal complexes as potential NLO materials, see for example: e) J. T. Lin. M.-F. Yang, C. Tsai, Y. S. Wen, J. Organomet. Chem. 1998, 564, 257.
106. For investigations into the potential use of multimetallic ethynylpyridyl scaffolds as molecular wires and multicentre magnetic materials, see: a) J. T. Lin, S.-S. Sun, J. J. Wu, L. Lee, K.-J. Lin, Y. F. Huang, Inorg. Chem. 1995, 34, 2323; b) A. J. Amoroso, A. M. W. Cargill Thompson, J. P. Maher, J. A. McCleverty, M. D. Ward, Inorg. Chem. 1995, 34, 4828. For the design of organic NLO materials with ethynylpyridines, see: c) reference [38c]. For a review on metalcoordinated conjugated pyridine ligands as NLO materials, see: d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229. For the synthesis of linear ethynylpyridine-type metal complexes as potential NLO materials, see for example: e) J. T. Lin. M.-F. Yang, C. Tsai, Y. S. Wen, J. Organomet. Chem. 1998, 564, 257.
107. For investigations into the potential use of multimetallic ethynylpyridyl scaffolds as molecular wires and multicentre magnetic materials, see: a) J. T. Lin, S.-S. Sun, J. J. Wu, L. Lee, K.-J. Lin, Y. F. Huang, Inorg. Chem. 1995, 34, 2323; b) A. J. Amoroso, A. M. W. Cargill Thompson, J. P. Maher, J. A. McCleverty, M. D. Ward, Inorg. Chem. 1995, 34, 4828. For the design of organic NLO materials with ethynylpyridines, see: c) reference [38c]. For a review on metalcoordinated conjugated pyridine ligands as NLO materials, see: d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229. For the synthesis of linear ethynylpyridine-type metal complexes as potential NLO materials, see for example: e) J. T. Lin. M.-F. Yang, C. Tsai, Y. S. Wen, J. Organomet. Chem. 1998, 564, 257.
108. For investigations into the potential use of multimetallic ethynylpyridyl scaffolds as molecular wires and multicentre magnetic materials, see: a) J. T. Lin, S.-S. Sun, J. J. Wu, L. Lee, K.-J. Lin, Y. F. Huang, Inorg. Chem. 1995, 34, 2323; b) A. J. Amoroso, A. M. W. Cargill Thompson, J. P. Maher, J. A. McCleverty, M. D. Ward, Inorg. Chem. 1995, 34, 4828. For the design of organic NLO materials with ethynylpyridines, see: c) reference [38c]. For a review on metalcoordinated conjugated pyridine ligands as NLO materials, see: d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229. For the synthesis of linear ethynylpyridine-type metal complexes as potential NLO materials, see for example: e) J. T. Lin. M.-F. Yang, C. Tsai, Y. S. Wen, J. Organomet. Chem. 1998, 564, 257.
109. For investigations into the potential use of multimetallic ethynylpyridyl scaffolds as molecular wires and multicentre magnetic materials, see: a) J. T. Lin, S.-S. Sun, J. J. Wu, L. Lee, K.-J. Lin, Y. F. Huang, Inorg. Chem. 1995, 34, 2323; b) A. J. Amoroso, A. M. W. Cargill Thompson, J. P. Maher, J. A. McCleverty, M. D. Ward, Inorg. Chem. 1995, 34, 4828. For the design of organic NLO materials with ethynylpyridines, see: c) reference [38c]. For a review on metalcoordinated conjugated pyridine ligands as NLO materials, see: d) H. Le Bozec, T. Renouard, Eur. J. Inorg. Chem. 2000, 229. For the synthesis of linear ethynylpyridine-type metal complexes as potential NLO materials, see for example: e) J. T. Lin. M.-F. Yang, C. Tsai, Y. S. Wen, J. Organomet. Chem. 1998, 564, 257.
110. For the use of ethynylpyridine-type ligands in the metal ion directed assembly of discrete supramolecular architectures, see: a) P. H. Dinolfo, J. T. Hupp, Chem. Mater. 2001, 13, 3113; b) C. J. Kuehl, S. D. Huang, P. J. Stang, J. Am. Chem. Soc. 2001, 123, 9634; c) K. R. Justin Thomas, J. T. Lin, Y.-Y. Lin, C. Tsai, S.-S. Sun, Organometallics 2001, 20, 2262.
111. For the use of ethynylpyridine-type ligands in the metal ion directed assembly of discrete supramolecular architectures, see: a) P. H. Dinolfo, J. T. Hupp, Chem. Mater. 2001, 13, 3113; b) C. J. Kuehl, S. D. Huang, P. J. Stang, J. Am. Chem. Soc. 2001, 123, 9634; c) K. R. Justin Thomas, J. T. Lin, Y.-Y. Lin, C. Tsai, S.-S. Sun, Organometallics 2001, 20, 2262.
112. For the use of ethynylpyridine-type ligands in the metal ion directed assembly of discrete supramolecular architectures, see: a) P. H. Dinolfo, J. T. Hupp, Chem. Mater. 2001, 13, 3113; b) C. J. Kuehl, S. D. Huang, P. J. Stang, J. Am. Chem. Soc. 2001, 123, 9634; c) K. R. Justin Thomas, J. T. Lin, Y.-Y. Lin, C. Tsai, S.-S. Sun, Organometallics 2001, 20, 2262.
113. J. S. Brumbaugh, A. Sen, J. Am. Chem. Soc. 1988, 110, 803.