Quadruple hydrogen bonded systems

Chemical Communications

Volumn , Issue 1, 2003, Pages 5-16

  Sijbesma, Rint P ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; POLYMER; PYRIMIDINONE DERIVATIVE;

ANISOTROPY; CHEMICAL STRUCTURE; COMPLEX FORMATION; COVALENT BOND; CRYSTAL STRUCTURE; DIMERIZATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; POLYMERIZATION; REVIEW; SUPRAMOLECULAR CHEMISTRY; THERMOSTABILITY; X RAY DIFFRACTION;

EID: 0037221490     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b205873c     Document Type: Review

References (72)

1. L. J. Prins, D. N. Reinhoudt and P. Timmerman, Angew. Chem., Int. Ed., 2001, 40, 2382-2426.
2. G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, Oxford, 1997.
3. S. C. Zimmerman and P. S. Corbin, Struct. Bonding (Berlin), 2000, 96, 63-94.
4. 1/2(n - 1)) (n = odd).
5. T. W. Bell and Z. Hou, Angew. Chem., Int. Ed., 1997, 36, 1536-1538.
6. S. K. Chang, D. Van Engen, E. Fan and A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 7640-7645.
7. J. Rebek, Chem. Soc. Rev., 1996, 25, 255-264.
8. D. T. Bong, T. D. Clark, J. R. Granja and M. R. Ghadiri, Angew. Chem., Int. Ed., 2001, 40, 988-1011.
9. D. C. Sherrington and K. A. Taskinen, Chem. Soc. Rev., 2001, 30, 83-93.
10. W. L. Jorgensen and J. Pranata, J. Am. Chem. Soc., 1990, 112, 2008; J. Pranata, S. G. Wierschke and W. L. Jorgensen, J. Am. Chem. Soc., 1991, 113, 2810.
11. W. L. Jorgensen and J. Pranata, J. Am. Chem. Soc., 1990, 112, 2008; J. Pranata, S. G. Wierschke and W. L. Jorgensen, J. Am. Chem. Soc., 1991, 113, 2810.
12. J. Sartorius and H.-J. Schneider, Chem. Eur. J., 1996, 2, 1446-1453.
13. L. Brunsveld, B. J. B. Folmer, E. W. Meijer and R. P. Sijbesma, Chem. Rev., 2001, 101, 4071-4098.
14. Supramolecular Polymers, ed. A. Ciferri, Marcel Dekker inc., New York, 2000.
15. N. Zimmerman, J. S. Moore and S. C. Zimmerman, Chem. Ind. (London), 1998, 604-610.
16. Y. Ducharme and J. D. Wuest, J. Org. Chem., 1988, 53, 5787-5789.
17. M. H. Krackov and C. M. Lee, J. Am. Chem. Soc., 1965, 87, 892-896.
18. P. L. Wash, E. Maverick, E. Chiefari and D. A. Lightner, J. Am. Chem. Soc., 1997, 119, 3806.
19. R. F. M. Lange and E. W. Meijer, Macromolecules, 1995, 28, 782-783; R. F. M. Lange and E. W. Meijer, Macromol. Symp., 1996, 102, 301-308.
20. R. F. M. Lange and E. W. Meijer, Macromolecules, 1995, 28, 782-783; R. F. M. Lange and E. W. Meijer, Macromol. Symp., 1996, 102, 301-308.
21. C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254-257; J.-M. Lehn, Macromol. Chem., Macromol. Symp., 1993, 69, 1-17; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci.USA, 1993, 90, 167; M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197-200; M. Kotera, J.-M. Lehn and J.-P. Vigneron, Tetrahedron, 1995, 51, 1953-72.
22. C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254-257; J.-M. Lehn, Macromol. Chem., Macromol. Symp., 1993, 69, 1-17; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci.USA, 1993, 90, 167; M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197-200; M. Kotera, J.-M. Lehn and J.-P. Vigneron, Tetrahedron, 1995, 51, 1953-72.
23. C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254-257; J.-M. Lehn, Macromol. Chem., Macromol. Symp., 1993, 69, 1-17; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci.USA, 1993, 90, 167; M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197-200; M. Kotera, J.-M. Lehn and J.-P. Vigneron, Tetrahedron, 1995, 51, 1953-72.
24. C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254-257; J.-M. Lehn, Macromol. Chem., Macromol. Symp., 1993, 69, 1-17; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci.USA, 1993, 90, 167; M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197-200; M. Kotera, J.-M. Lehn and J.-P. Vigneron, Tetrahedron, 1995, 51, 1953-72.
25. C. Fouquey, J.-M. Lehn and A.-M. Levelut, Adv. Mater., 1990, 2, 254-257; J.-M. Lehn, Macromol. Chem., Macromol. Symp., 1993, 69, 1-17; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci.USA, 1993, 90, 167; M. Kotera, J.-M. Lehn and J.-P. Vigneron, J. Chem. Soc., Chem. Commun., 1994, 197-200; M. Kotera, J.-M. Lehn and J.-P. Vigneron, Tetrahedron, 1995, 51, 1953-72.
26. F. H. Beijer, R. P. Sijbesma, J. A. J. M. Vekemans, E. W. Meijer, H. Kooijman and A. L. Spek, J. Org. Chem., 1996, 61, 6371-6380.
27. A. R. Katritzky and I. Ghiviriga, J. Chem. Soc., Perkin Trans. 2, 1995, 1653.
28. F. H. Beijer, H. Kooijman, A. L. Spek, R. P. Sijbesma and E. W. Meijer, Angew. Chem., Int. Ed., 1998, 37, 75-78.
29. R. J. Griffin and P. R. Lowe, J. Chem. Soc., Perkin Trans. 1, 1992, 1811-1819.
30. F. H. Beijer, PhD Thesis, Technische Universiteit Eindhoven, 1998.
31. J. H. K. K. Hirschberg, L. Brunsveld, A. Ramzi, J. A. J. M. Vekemans, R. P. Sijbesma and E. W. Meijer, Nature, 2000, 407, 167-170.
32. L. Brunsveld, J. A. J. M. Vekemans, J. H. K. K. Hirschberg, R. P. Sijbesma and E. W. Meijer, Proc. Natl. Acad. Sci., 2002, 99, 4977-4982.
33. C. M. Drain, X. Shi, T. Milic and F. Nifiatis, Chem. Commun., 2001, 287-288.
34. G. Ercolani, Chem. Commun., 2001, 1416-1417.
35. F. H. Beijer, R. P. Sijbesma, J. A. J. M. Vekemans, E. W. Meijer, H. Kooijman and A. L. Spek, J. Org. Chem., 1996, 61, 6371-6380.
36. D. J. Brown, R. F. Evans, W. B. Cowden and M. D. Fenn, The Pyrimidines, Wiley, New York, 1994, p. 193-196.
37. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm., 1981, 314, 34-41; J. Krepelka; A. Cerny, R. Kotva, J. Vachek and M. Melka, Collect. Czech. Chem. Commun., 1986, 51, 1140-1149; G. Vasilev, Dokl. Bolg. Akad. Nauk., 1990, 43, 57-60 (Chem. Abstr., 115, 49603); J. Fan and C. C. Cheng, J.Heterocycl. Chem., 1993, 30, 1273-1276.
38. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm., 1981, 314, 34-41; J. Krepelka; A. Cerny, R. Kotva, J. Vachek and M. Melka, Collect. Czech. Chem. Commun., 1986, 51, 1140-1149; G. Vasilev, Dokl. Bolg. Akad. Nauk., 1990, 43, 57-60 (Chem. Abstr., 115, 49603); J. Fan and C. C. Cheng, J.Heterocycl. Chem., 1993, 30, 1273-1276.
39. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm., 1981, 314, 34-41; J. Krepelka; A. Cerny, R. Kotva, J. Vachek and M. Melka, Collect. Czech. Chem. Commun., 1986, 51, 1140-1149; G. Vasilev, Dokl. Bolg. Akad. Nauk., 1990, 43, 57-60 (Chem. Abstr., 115, 49603); J. Fan and C. C. Cheng, J.Heterocycl. Chem., 1993, 30, 1273-1276.
40. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm., 1981, 314, 34-41; J. Krepelka; A. Cerny, R. Kotva, J. Vachek and M. Melka, Collect. Czech. Chem. Commun., 1986, 51, 1140-1149; G. Vasilev, Dokl. Bolg. Akad. Nauk., 1990, 43, 57-60 (Chem. Abstr., 115, 49603); J. Fan and C. C. Cheng, J.Heterocycl. Chem., 1993, 30, 1273-1276.
41. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm., 1981, 314, 34-41; J. Krepelka; A. Cerny, R. Kotva, J. Vachek and M. Melka, Collect. Czech. Chem. Commun., 1986, 51, 1140-1149; G. Vasilev, Dokl. Bolg. Akad. Nauk., 1990, 43, 57-60 (Chem. Abstr., 115, 49603); J. Fan and C. C. Cheng, J.Heterocycl. Chem., 1993, 30, 1273-1276.
42. F. H. Beijer, R. P. Sijbesma, H. Kooijman, A. L. Spek and E. W. Meijer, J. Am. Chem. Soc., 1998, 120, 6761-6769.
43. S. H. M. Söntjens, R. P. Sijbesma, M. H. P. van Genderen and E. W. Meijer, J. Am. Chem. Soc., 2000, 122, 7487-7493.
44. G. Armstrong and M. Buggy, Mater. Sci. Eng., C: Biomimetic Supramol. Syst., 2001, 18, 45-49.
45. P. S. Corbin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9710-9711.
46. P. S. Corbin and S. C. Zimmerman, J. Am. Chem. Soc., 2000, 122, 3779-3780.
47. A. El-ghayoury, E. Peeters, A. P. H. J. Schenning and E. W. Meijer, Chem. Commun., 2000, 1969-1970.
48. Y. Tokunaga and T. Seo, Chem. Commun., 2002, 970-971.
49. J. J. Gonzalez, J. de Mendoza, S. Gonzalez, E. M. Priego, N. Martin, C. Luo and D. M. Guldi, Chem. Commun., 2001, 163-164.
50. M. T. Rispens, L. Sanchez, J. Knol and J. C. Hummelen, Chem. Commun., 2001, 161-162.
51. L. Sanchez, M. T. Rispens and J. C. Hummelen, Angew. Chem., Int. Ed., 2002, 41, 838-840.
52. J. L. Sessler and R. Wang, J. Org. Chem., 1998, 63, 4079-4091.
53. H. Kagechika, I. Azamuya, A. Tanati, K. Yamaguchi and K. Shudo, Tetrahedron Lett., 1999, 40, 3423-3426.
54. B. J. B. Folmer, R. P. Sijbesma, H. Kooijman, A. L. Spek and E. W. Meijer, J. Am. Chem. Soc., 1999, 121, 2001-2007.
55. J. J. Gonzalez, P. Prados and J. de Mendoza, Angew. Chem., Int. Ed., 1999, 38, 525-528.
56. R. P. Sijbesma, F. H. Beijer, L. Brunsveld, B. J. B. Folmer, J. H. K. K. Hirschberg, R. F. M. Lange, J. K. L. Lowe and E. W. Meijer, Science, 1997, 278, 1601-1604.
57. B. J. B. Folmer, E. Cavini, R. P. Sijbesma and E. W. Meijer, Chem. Commun., 1998, 1847-1848.
58. J. H. K. K. Hirschberg, F. H. Beijer, H. A. van Aert, P. C. M. M. Magusin, R. P. Sijbesma and E. W. Meijer, Macromolecules, 1999, 32, 2696-2705.
59. B. J. B. Folmer, R. P. Sijbesma, R. M. Versteegen, J. A. J. van der Rijt and E. W. Meijer, Adv. Mater., 2000, 12, 874-878.
60. R. F. M. Lange, M. van Gurp and E. W. Meijer, J. Pol. Sci. A, Pol. Chem., 1999, 37, 3657-3670.
61. L. R. Rieth, R. F. Eaton and G. W. Coates, Angew. Chem., Int. Ed., 2001, 40, 2153-2156.
62. S. H. M. Söntjens, R. P. Sijbesma, M. H. P. van Genderen and E. W. Meijer, Macromolecules, 2001, 34, 3815-3818.
63. B. J. B. Folmer, R. P. Sijbesma and E. W. Meijer, J. Am. Chem. Soc., 2001, 123, 2093-2094.
64. A. P. Davis, S. M. Draper, G. Dunne and P. Ashton, Chem. Commun., 1999, 2266, 2265-2266.
65. U. Luning and C. Kuhl, Tetrahedron Lett., 1998, 39, 5735-5738.
66. S. H. M. Söntjens, J. T. Meijer, H. Kooijman, A. L. Spek, M. H. P. van Genderen, R. P. Sijbesma and E. W. Meijer, Org. Lett., 2001, 3, 3887-3889.
67. B. Gong, Y. Yan, H. Zeng, E. Skrzypczak-Jankunn, Y. W. Kim, J. Zhu and H. Ickes, J. Am. Chem. Soc., 1999, 121, 5607-5609.
68. H. Zeng, R. S. Miller, R. A. Flowers and B. Gong, J. Am. Chem. Soc., 2000, 122, 2635-2644.
69. H. Zeng, H. Ickes, R. A. F. Ii and B. Gong, J. Org. Chem., 2001, 66, 3574-3583.
70. J. H. Hartley, T. D. James and C. J. Ward, J. Chem. Soc., Perkin Trans. 1, 2000, 3155-3184.
71. J. Ruokolainen, R. Makinen, M. Torkkeli, T. Makela, R. Serimaa, G. ten Brinke and O. Ikkala, Science, 1998, 280, 557-560.
72. S.-Q. Zhang, K. Fukase, M. Izumi, Y. Fukase and S. Kusumoto, Synlett, 2001, 590-596.