Bis-ureidodeazapterin (Bis-DeAP) as a general route to supramolecular star polymers

Tetrahedron

Volumn 64, Issue 36, 2008, Pages 8558-8570

  Todd, Eric M ^a   Zimmerman, Steven C ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 2 METHYLPROPANOYL BROMIDE; BISUREIDODEAZAPTERIN; BROMINE DERIVATIVE; HETEROCYCLIC COMPOUND; MACROGOL; METHACRYLIC ACID METHYL ESTER; N,N DIMETHYLFORMAMIDE; POLYMER; TOLUENE;

ARTICLE; HYDROGEN BOND; MOLECULAR RECOGNITION; MOLECULAR WEIGHT; PRIORITY JOURNAL; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 47949127359     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.076     Document Type: Article

References (74)

1. For a general review of supramolecular polymers, see:. Lehn J.-M. Makromol. Chem., Macromol. Symp. 69 (1993) 1-17
2. Zeng F., and Zimmerman S.C. Chem. Rev. 97 (1997) 1681-1712
3. Zimmerman N., Moore J.S., and Zimmerman S.C. Chem. Ind. (1998) 604-610
4. Brunsveld L., Folmer B.J.B., Meijer E.W., and Sijbesma R.P. Chem. Rev. 101 (2001) 4071-4097
5. In: Ciferri A. (Ed). Supramolecular Polymers. 2nd ed. (2005), CRC, Boca Raton, FL
6. ten Cate A.T., and Sijbesma R.P. Macromol. Rapid Commun. 23 (2002) 1094-1112
7. Selected reviews:
8. Lehn J.-M. Angew. Chem., Int. Ed. Engl. 29 (1990) 1304-1319
9. Fredericks J., Yang J., Geib S.J., and Hamilton A.D. Proc. Indian Acad. Sci., Chem. Sci. 106 (1994) 923-935
10. Whitesides G.M., Simanek E.E., Mathias J.P., Seto C.T., Chin D.N., Mammen M., and Gordon D.M. Acc. Chem. Res. 28 (1995) 37-44
11. Lawrence D.S., Jiang T., and Levett M. Chem. Rev. 95 (1995) 2229-2260
12. Conn M.M., and Rebek Jr. J. Chem. Rev. 97 (1997) 1647-1668
13. Zimmerman S.C., and Corbin P.S. Struct. Bonding 96 (2000) 63-94
14. Prins L.J., Reinhoudt D.N., and Timmerman P. Angew. Chem., Int. Ed. 40 (2001) 2382-2426
15. Archer E.A., Gong H., and Krische M.J. Tetrahedron 57 (2001) 1139-1159
16. Jeffery T.D. Angew. Chem., Int. Ed. 43 (2004) 668-698
17. Beijer F.H., Sijbesma R.P., Kooijman H., Spek A.L., and Meijer E.W. J. Am. Chem. Soc. 120 (1998) 6761-6769
18. Sontjens S.H.M., Sijbesma R.P., van Genderen M.H.P., and Meijer E.W. J. Am. Chem. Soc. 122 (2000) 7487-7493
19. Bosman A.W., Sijbesma R.P., and Meijer E.W. Mater. Today 7 (2004) 34-39
20. Park T., and Zimmerman S.C. J. Am. Chem. Soc. 128 (2006) 14236-14237
21. Park T., and Zimmerman S.C. J. Am. Chem. Soc. 128 (2006) 11582-11590
22. Ong H.C., and Zimmerman S.C. Org. Lett. 8 (2006) 1589-1592
23. Park T., Todd E.M., Nakashima S., and Zimmerman S.C. J. Am. Chem. Soc. 127 (2005) 18133-18142
24. Park T., Zimmerman S.C., and Nakashima S. J. Am. Chem. Soc. 127 (2005) 6520-6521
25. Todd E.M., Quinn J.R., Park T., and Zimmerman S.C. Isr. J. Chem. 45 (2005) 381-389
26. Selected examples of heterocycles that form cyclic assemblies:
27. Zerkowski J.A., Seto C.T., and Whitesides G.M. J. Am. Chem. Soc. 114 (1992) 5473-5475
28. Vreekamp R.H., van Duynhoven J.P.M., Hubert M., Verboom W., and Reinhoudt D.N. Angew. Chem., Int. Ed. 35 (1996) 1215-1218
29. Marsh A., Silvestri M., and Lehn J.-M. Chem. Commun. (1996) 1527-1528
30. Mascal M., Hext N.M., Warmuth R., Moore M.H., and Turkenburg J.P. Angew. Chem., Int. Ed. 35 (1996) 2204-2206
31. Fenniri H., Mathivanan P., Vidale K.L., Sherman D.M., Hallenga K., Wood K.V., and Stowell J.G. J. Am. Chem. Soc. 123 (2001) 3854-3855
32. Keizer H.M., Gonzalez J.J., Segura M., Prados P., Sijbesma R.P., Meijer E.W., and de Mendoza J. Chem.-Eur. J. 11 (2005) 4602-4608
33. Zimmerman S.C., and Duerr B.F. J. Org. Chem. 57 (1992) 2215-2217
34. Boucher E., Simard M., and Wuest J.D. J. Org. Chem. 60 (1995) 1408-1412
35. Yang J., Fan E., Geib S.J., and Hamilton A.D. J. Am. Chem. Soc. 115 (1993) 5314-5315
36. Tirumala S., and Davis J.T. J. Am. Chem. Soc. 119 (1997) 2769-2776
37. Shi X., Fettinger J.C., Cai M., and Davis J.T. Angew. Chem., Int. Ed. 39 (2000) 3124-3127
38. Cyclic, hydrogen-bonded self-assembled dendrimers:
39. Zimmerman S.C., Zeng F., Reichert D.E.C., and Kolotuchin S.V. Science 271 (1996) 1095-1098
40. Corbin P.S., Lawless L.J., Li Z.T., Ma Y.G., Witmer M.J., and Zimmerman S.C. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 5099-5104
41. Ma Y., Kolotuchin S.V., and Zimmerman S.C. J. Am. Chem. Soc. 124 (2002) 13757-13769
42. Zeng F., Zimmerman S.C., Kolotuchin S.V., Reichert D.E.C., and Ma Y. Tetrahedron 58 (2002) 825-843
43. Noncyclic self-assembled dendrimers:
44. Wang Y., Zeng F., and Zimmerman S.C. Tetrahedron Lett. 38 (1997) 5459-5462
45. Partridge K.S., Smith D.K., Dykes G.M., and McGrail P.T. Chem. Commun. (2001) 319-320
46. Mulder A., Huskens J., and Reinhoudt D.N. Org. Biomol. Chem. 2 (2004) 3409-3424
47. Initial results were reported in a communication:. Todd E.M., and Zimmerman S.C. J. Am. Chem. Soc. 129 (2007) 14534-14535
48. A recently reported recognition unit by Mascal and coworkers allows for the attachment of additional functionality, however, this module was not functionalized:. Mascal M., Farmer S.C., and Arnall-Culliford J.R. J. Org. Chem. 71 (2006) 8146-8150
49. Keizer H.M., Sijbesma R.P., and Meijer E.W. Eur. J. Org. Chem. (2004) 2553-2555
50. Corbin P.S., and Zimmerman S.C. J. Am. Chem. Soc. 120 (1998) 9710-9711
51. 6=4096, however, the total number of distinguishable isomers is less than this amount.
52. Selected reviews:
53. Bielawski C.W., and Grubbs R.H. Prog. Polym. Sci. 32 (2007) 1-29
54. Hawker C.J., Bosman A.W., and Harth E. Chem. Rev. 101 (2001) 3661-3688
55. Matyjaszewski K., and Xia J.H. Chem. Rev. 101 (2001) 2921-2990
56. Shiau L.-D. Macromol. Theory Simul. 13 (2004) 783-789
57. Zhu S., Li D., Yu Q., and Hunkeler D. J. Macromol. Sci., Pure Appl. Chem. 35 (1998) 33-56
58. Nowick J.S., and Chen J.S. J. Am. Chem. Soc. 114 (1992) 1107-1108
59. Fan E., Van Arman S.A., Kincaid S., and Hamilton A.D. J. Am. Chem. Soc. 115 (1993) 369-370
60. Torneiro M., and Still W.C. J. Am. Chem. Soc. 117 (1995) 5887-5888
61. Kato Y., Conn M.M., and Rebek Jr. J. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 1208-1212
62. Hirschberg J.H.K.K., Brunsveld L., Ramzi A., Vekemans J.A.J.M., Sijbesma R.P., and Meijer E.W. Nature 407 (2000) 167-170
63. Brunsveld L., Vekemans J.A.J.M., Hirschberg J.H.K.K., Sijbesma R.P., and Meijer E.W. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 4977-4982
64. Zeng H., Yang X., Flowers R.A., and Gong B. J. Am. Chem. Soc. 124 (2002) 2903-2910
65. Li M., Yamato K., Ferguson J.S., and Gong B. J. Am. Chem. Soc. 128 (2006) 12628-12629
66. Selected reviews:
67. Paleos C.M., and Tsiourvas D. Adv. Mater. 9 (1997) 695-710
68. Ariga K., and Kunitake T. Acc. Chem. Res. 31 (1998) 371-378
69. Gitsov I., and Frèchet J.M.J. J. Am. Chem. Soc. 118 (1996) 3785-3786
70. Kang S.K., Kim W.S., and Moon B.H. Synthesis (1985) 1161-1162
71. Organic Syntheses; John Wiley & Sons: New York, NY, 1941; Coll. Vol. 1, p 219;
72. Organic Syntheses; John Wiley & Sons: New York, NY, 1927; Coll. Vol. 7, p 28;
73. Sidgwick N.V., and Taylor T.W.J. J. Chem. Soc., Trans. 121 (1922) 1853-1859
74. Pfleiderer M., and Pfleiderer W. Heterocycles 33 (1992) 905-929