Sequences in Dendrons and Dendrimers

Journal of Organic Chemistry

Volumn 69, Issue 9, 2004, Pages 2937-2944

  Sivanandan, Kulandaivelu ^a   Sandanaraj, Britto S ^a   Thayumanavan, S ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROMOLECULES; MONOMERS; SYNTHESIS (CHEMICAL);

BIOMACROMOLECULES; DENDRONS;

DENDRIMERS;

ABB MONOMER; DENDRIMER; DENDRON; FUNCTIONAL GROUP; MONOMER; UNCLASSIFIED DRUG;

ARTICLE; BIOMOLECULAR ELECTRONICS; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; MACROMOLECULE; MOLECULAR MIMICRY; POLYMERIZATION; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

BIOMIMETIC MATERIALS; BIOPOLYMERS; ETHERS; HYDROCARBONS, HALOGENATED; HYDROPHOBICITY; MOLECULAR STRUCTURE; PHENOLS;

EID: 2142708651     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049878p     Document Type: Article

References (68)

1. (a) Wang, L.; Brock, A.; Herberich, B.; Schultz, P. G. Science 2001, 292, 498-500.
2. (b) Wang, P.; Tang, Y.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 6900-6906.
3. (c) Wang, L.; Zhang, Z.; Brock, A.; Schultz, P. G. Proc. Natl. Acad. Sci. U.S.A. 2003; 100, 56-61.
4. (d) Kwon, I.; Kishenbaum, K.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 7512-7513.
5. (e) Hohsaka, T.; Ashizuka, Y.; Sasaki, H.; Murakami, H.; Sisido, M. J. Am. Chem. Soc. 1999, 121, 12194-12195.
6. (f) Anderson, R. D., III; Zhou, J.; Hecht, S. M. J. Am. Chem. Soc. 2002, 124, 9674-9675.
7. (a) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304-1319.
8. (b) Conn, M. M.; Rebek, J. Chem. Rev. 1997, 97, 1647-1668.
9. (c) Rebek, J. Acc. Chem. Res. 1999, 32, 278-286.
10. (d) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.
11. (e) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
12. (f) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296.
13. (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
14. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4012.
15. (c) Liu, L.; Rozenman, M.; Breslow, R. J. Am. Chem. Soc. 2002, 124, 12660-12661.
16. (d) Liu, L.; Breslow, R. J. Am. Chem. Soc. 2003, 125, 12110-12111.
17. (e) Liu, L.; Breslow, R. J. Am. Chem. Soc. 2002, 124, 4978-4979.
18. (a) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications, 2nd ed.; Wiley-VCH: New York, 2001.
19. (b) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
20. (c) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 884-905.
21. (d) Fréchet, J. M. J. Science 1994, 263, 1710-1715.
22. (e) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
23. (f) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
24. (g) Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689-1746.
25. (h) Tomalia, D. A. Adv. Mater. 1994, 6, 529-539.
26. (i) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138-175.
27. (j) Dendrimers II: Architecture, Nanostructure and Supramolecular Chemistry; Vögtle, F., Ed.; Springer: Berlin, 2000; Vol. 210.
28. (l) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
29. (a) Diederich, F.; Felber, B. Proc. Nat. Acad. Sci. U.S.A. 2002, 59, 4778-4781.
30. (b) Baars, M. W. P. L.; Meijer, E. W. Top. Curr. Chem. 2000, 210, 131-182.
31. (c) Zimmerman, S. C.; Lawless, L. J. Top. Curr. Chem. 2001, 217, 95-120.
32. (d) Thayumanavan, S.; Bharathi, P.; Sivanandan, K.; Vutukuri, D. R. C. R. Acad. Sci., Ser. IIc: Chim. 2003, 6, 767-778.
33. (a) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
34. (b) Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34, 60-71.
35. (c) Stone, D. L.; Smith, D. K.; McGrail, P. T. J. Am. Chem. Soc. 2002, 124, 856-864.
36. (d) Smith, D. K.; Diederich, F. Top. Curr. Chem. 2000, 210, 183-227.
37. (e) Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181-190.
38. (a) Smith, D. K.; Diederich, F. Chem. Eur. J. 1998, 4, 1353-1361.
39. (b) Dandliker, P. J.; Diederich, F.; Gisselbrecht, J. P.; Louati, A.; Gross, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2725-2728.
40. (c) Mattei, S.; Wallimann, P.; Kenda, B.; Amrein, W.; Diederich, F. Helv. Chim. Acta 1997, 80, 2391-2417.
41. (d) Habicher, T.; Diederich, F.; Gramlich, V. Helv. Chim. Acta 1999, 82, 1066-1095.
42. (e) Wallimann, P.; Mattei, S.; Seiler, P.; Diederich, F. Helv. Chim. Acta 1997, 80, 2369-2390.
43. (f) Jiang, D. L.; Aida, T. Chem. Commun. 1996, 1523-1524.
44. (g) Bharathi, P.; Zhao, H.; Thayumanavan, S. Org. Lett. 2001, 3, 1961-1964.
45. Watkins, D. M.; Sayed-Sweet, Y.; Klimash, J. W.; Turro, N. J.; Tomalia, D. A. Langmuir 1997, 13, 3136-3141.
46. For examples, see: (a) Daniel, M. C.; Ruiz, J.; Astruc, D. J. Am. Chem. Soc. 2003, 125, 1150-1151.
47. (b) Piotti, M. E., Jr.; F. R.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471-9472.
48. (c) Koenig, S.; Müller, L.; Smith, D. K. Chem. Eur. J. 2001, 7, 979-986.
49. (a) Newkome, G. R.; Weis, C. D.; Moorefield, C. N.; Baker, G. R.; Childs, B. J.; Epperson, J. Angew. Chem., Int. Ed. 1996, 37, 307-310.
50. (b) Newkome, G. R.; Kim, H. J.; Moorefield, C. N.; Maddi, H.; Yoo, K.-S. Macromolecules 2003, 36, 4345-4354.
51. (c) Newkome, G. R.; Yoo, K. S.; Hwang, S.-H.; Moorefield, C. N. Tetrahedron 2003, 59, 3955-3964.
52. (d) Larré, C.; Donnadieu, B.; Caminade, A.-M.; Majoral, J.-P. J. Am. Chem. Soc. 1998, 120, 4029-4030.
53. (e) Latigue, M.-L.; Slany, M.; Caminade, A.-M.; Majoral, J.-P. Chem. Eur. J. 1996, 2, 1417-1426.
54. (f) Woller, E. K.; Walter, E. D.; Morgan, J. R.; Singel, D. J.; Cloninger, M. J. J. Am. Chem. Soc. 2003, 125, 8820-8826.
55. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3868.
56. (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1991, 1059-1076.
57. (b) Bo, Z.; Schäfer, A.; Franke, P.; Schlüter, A. D. Org. Lett. 2000, 2, 1645-1648.
58. (c) Ganesh, R. N.; Shraberg, J.; Sheridan, P. G.; Thayumanavan, S. Tetrahedron Lett. 2002, 43, 7217-7220.
59. (d) For differential substitutions in layer by layer, see: Freeman, A. W.; Chrisstoffels, L. A. J.; Fréchet, J. M. J. J. Org. Chem. 2000, 65, 7612-7617.
60. (e) For synthesis of dendrimers using different branching structures in one pot, see: Okaniwa, M.; Takeuchi, K.; Asai, M.; Ueda, M. Macromolecules 2002, 35, 6224-6231; 6232-6238.
61. (a) Sivanandan, K.; Vutukuri, D.; Thayumanavan, S. Org. Lett. 2002, 4, 3751-3753.
62. (b) Vutukuri, D.; Sivanandan, K.; Thayumanavan, S. Chem. Commun. 2003, 796-797.
63. (c) Simanek and co-workers reported a methodology in which the differential reactivities of di-, mono-, and unsubstituted cyanuric chloride have been utilized. See: Zeng, W.; Nowlan, D. T., III; Thomson, L. M.; Lackowski, W. M.; Simanek, E. E. J. Am. Chem. Soc. 2001, 123, 8914-8922.
64. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
65. Compound 26 was obtained from 5-bromo-resorcinol, which was synthesized from 3,5-dimethoxybenzoic acid using the procedures reported in: Dol, G. C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Eur. J. Org. Chem. 1998, 359, 9-364.
66. Synthesis of 31 is illustrated in Scheme 11 within Supporting Information.
67. For an interesting example in which copies of the same functionality are incorporated in the dendritic interior, see: Zimmerman, S. C.; Wendland, M. S.; Rakow, N. A.; Zharov, I.; Suslick, K. S. Nature 2002, 418, 399-403.
68. (b) Zimmerman, S. C.; Zharov, I.; Wendland, M. S.; Rakow, N. A.; Suslick, K. S. J. Am. Chem. Soc. 2003, 125, 13504-13518.