Expanding the structural diversity of self-assembling dendrons and supramolecular dendrimers via complex building blocks

Journal of the American Chemical Society

Volumn 129, Issue 36, 2007, Pages 11265-11278

  Percec, Virgil ^a   Won, Betty C ^a   Peterca, Mihai ^a   Heiney, Paul A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRONS; RETROSTRUCTURAL ANALYSIS; SUPRAMOLECULAR DENDRIMERS; X-RAY PATTERNS;

ETHERS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); THICKNESS MEASUREMENT; X RAY DIFFRACTION;

DENDRIMERS;

ANTHRACENE DERIVATIVE; DENDRIMER; DENDRON DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BROMINATION; CHEMICAL STRUCTURE; OXIDATION; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; DENDRIMERS; MOLECULAR BIOLOGY; MOLECULAR STRUCTURE; X-RAY DIFFRACTION;

EID: 34548733693     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073714j     Document Type: Article

References (130)

1. (a) Fréchet, J. M. J., Tomalia, D. A., Eds. Dendrimers and Other Dendritic Polymers; Wiley: New York 2001.
2. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons; Wiley-VCH: Weinheim, 2001.
3. (a) Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155-158.
4. (b) Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117-132.
5. (c) Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003-2004.
6. (a) Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
7. (b) Miller, T. M.; Neenan, T. X. Chem. Mater. 1990, 2, 346-349.
8. (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
9. (b) Kim, Y.; Zimmerman, S. C. Curr. Opin. Chem. Biol. 1998, 2, 733-742.
10. (c) Seebach, D.; Rheiner, P. B.; Greiveldinger, G.; Butz, T.; Sellner, H. Top. Curr. Chem. 1998, 197, 125-164.
11. (d) Majoral, J.-P.; Caminade, A.-M. Top. Curr. Chem. 1998, 197, 79-124.
12. (e) Smith, D. K.; Diederich, F. Chem. - Eur. J. 1998, 4, 1353-1361.
13. (f) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 885-905.
14. (g) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
15. (h) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3024.
16. (i) Haag, R. Chem. - Eur. J. 2001, 7, 327-335.
17. (j) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
18. (k) Tully, D. C.; Fréchet, J. M. J. Chem. Commun. 2001, 1229-1239.
19. (l) Stiriba, S.-E.; Frey, H.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 1329-1334.
20. (m) Esfand, R.; Tomalia, D. A. Drug Discovery Today 2001, 6, 427-436.
21. (n) Gillies, E. R.; Fréchet, J. M. J. Drug Discovery Today 2005, 10, 35-43.
22. (o) Jiang, D.-L.; Aida, T. Prog. Polym. Sci. 2005, 30, 403-422.
23. (p) Van de Coevering, R.; Gebbink, R. J. M. K.; Van Koten, G. Prog. Polym. Sci. 2005, 30, 474-490.
24. (q) Caminade, A.-M.; Majoral, J.-P. Prog. Polym. Sci. 2005, 30, 491-505.
25. (r) Boas, U.; Heegaard, P. M. H. Chem. Soc. Rev. 2004, 33, 43-63.
26. (s) Grinstaff, M. W. Chem. - Eur. J. 2002, 8, 2838-2846.
27. (t) Grayson, S. M.; Fréchet, J. M. J.; Chem. Rev. 2001, 101, 3819-3867.
28. (u) Shabat, D. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1569-1578.
29. (v) Frauenrath, H. Prog. Polym. Sci. 2005, 30, 325-384.
30. For selected recent reviews on supramolecular dendrimers self-organized into periodic arrays, see: (a) Zimmerman, S. C. Curr. Opin. Colloid Interface Sci. 1997, 2, 89-99.
31. (b) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
32. (c) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 885-905.
33. (d) Emrick, T.; Fréchet, J. M. J. Curr. Opin. Colloid Interface Sci. 1999, 4, 15-23.
34. (e) Schlenk, C.; Frey, H. Monatsh. Chem. 1999, 130, 3-14.
35. (f) Smith, D. K.; Diederich, F. Top. Curr. Chem. 2000, 210, 183-227.
36. (g) Ponomarenko, S. A.; Boiko, N. I.; Shibaev, V. P. Polym. Sci. Ser. C 2001, 43, 1-45.
37. (h) Guillon, D.; Deschenaux, R. Curr. Opin. Solid State Mater. Sci. 2002, 6, 515-525.
38. (i) Tschierske, C. Curr. Opin. Colloid Interface Sci. 2002, 7, 69-80.
39. (j) Diele, S. Curr. Opin. Colloid Interface Sci. 2002, 7, 333-342.
40. (k) Caminade, A.-M.; Turrin, C.-O.; Sutra, P.; Majoral, J.-P. Curr. Opin. Colloid Interface Sci. 2003, 8, 282-295.
41. (l) Smith, D. K.; Hirst, A. R.; Love, C. S.; Hardy, J. G.; Brignell, S. V.; Huang, B. Prog. Polym. Sci. 2005, 30, 220-293.
42. (m) Percec, V. Philos. Trans. R. Soc. London. Ser. A 2006, 364, 2709-2719.
43. (n) Rudick, J. C.; Percec, V. New J. Chem. 2007, 31, 1083-1096.
44. (o) Donnio, B.; Guillon, D. Adv. Polym. Sci. 2006, 201, 45-155.
45. 3 repeat units, see: (a) Percec, V; Johansson, G.; Heck, J.; Ungar, G.; Batty, S. V. J. Chem. Soc., Perkin Trans. 1 1993, 1411-1420.
46. (b) Johansson, G.; Percec, V.; Ungar, G.; Abramic, D. J. Chem. Soc., Perkin Trans. 1 1994, 447-459.
47. (c) Percec, V.; Johansson, G.; Ungar, G.; Zhou, J. J. Am. Chem. Soc. 1996, 118, 9855-9866.
48. (d) Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G. J. Am. Chem. Soc. 1997, 119, 1539-1555.
49. (e) Hudson, S. D.; Jung, H.-T.; Percec, V.; Cho, W.-D.; Johansson, G.; Ungar, G.; Balagurusamy, V. S. K. Science 1997, 278, 449-452.
50. (f) Percec, V.; Cho, W.-D.; Mosier, P. E.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 1998, 120, 11061-11070.
51. (g) Ungar, G.; Percec, V.; Holerca, M. N.; Johannson, G.; Heck, J. A. Chem. - Eur. J. 2000, 6, 1258-1266.
52. (h) Percec, V.; Cho, W.-D.; Möller, M.; Prokhorova, S. A.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 2000, 122, 4249-4250.
53. (i) Percec, V.; Cho, W.-D.; Ungar, G. J. Am. Chem. Soc. 2000, 122, 10273-10281.
54. (j) Dukeson, D. R.; Ungar, G.; Balagurusamy, V. S. K.; Percec, V.; Johansson, G. A.; Glodde, M. J. Am. Chem. Soc. 2003, 125, 15974-15980.
55. (k) Percec, V.; Glodde, M.; Johansson, G.; Balagurusamy, V. S. K.; Heiney, P. A. Angew. Chem., Int. Ed. 2003, 42, 4338-4342.
56. (l) Malthête, J. New J. Chem. 1996, 20, 925-928.
57. (m) Percec, V.; Peterca, M.; Sienkowska, M. J.; Ilies, M. A.; Aqad, E.; Smidrkal, J.; Heiney, P. A. J. Am. Chem. Soc. 2006, 128, 3324-3334.
58. (n) Percec, V.; Holerca, M. N.; Nummelin, S.; Morrison, J. L.; Glodde, M.; Smidrkal, J.; Peterca, M.; Rosen, B. M.; Uchida, S.; Balagurusamy, V. S. K.; Sienkowska, M. J.; Heiney, P. A. Chem. - Eur. J. 2006, 12, 6216-6241.
59. 2 repeat units, see: (a) Percec, V.; Cho, W.-D.; Ungar, G.; Yeardley, D. J. P. Angew. Chem., Int. Ed. 2000, 39, 1598-1602.
60. (b) Percec, V.; Cho, W.-D.; Ungar, G.; Yeardley, D. J. P. J. Am. Chem. Soc. 2001, 123, 1302-1315.
61. (c) Suárez, M.; Lehn, J.-M.; Zimmerman, S. C.; Skoulios, A.; Heinrich, B. J. Am. Chem. Soc. 1998, 120, 9526-9532.
62. 3 benzyl ether and other hybrid dendrons, see: (a) Percec, V.; Mitchell, C. M.; Cho, W.-D.; Uchida, S.; Glodde, M.; Ungar, G.; Zeng, X.; Liu, Y.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2004, 126, 6078-6094.
63. (b) Percec, V.; Smidrkal, J.; Peterca, M.; Mitchell, C. M.; Nummelin, S.; Dulcey, A. E.; Sienkowska, M. J.; Heiney, P. A. Chem. - Eur. J. 2007, 13, 3989-4007.
64. For examples of dendrons that self-assemble and co-assemble into supramolecular lattices and/or complex supramolecules, see: (a) Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem. - Eur. J. 1999, 5, 1070-1083.
65. (b) Percec, V.; Bera, T. K.; Glodde, M.; Fu, Q.; Balagurusamy, V. S. K.; Heiney, P. A. Chem. - Eur. J. 2003, 9, 921-935.
66. (c) Percec, V.; Imam, M. R.; Bera, T. K.; Balagurusamy, V. S. K.; Peterca, M.; Heiney, P. A. Angew. Chem., Int. Ed. 2005, 44, 4739-4745.
67. For new periodic and quasi-periodic lattices self-organized from supramolecular dendrimers, see: (a) Ungar, G.; Liu, Y.; Zeng, X.; Percec, V.; Cho, W.-D. Science 2003, 299, 1208-1211.
68. (b) Zeng, X.; Ungar, G.; Liu, Y.; Percec, V.; Dulcey, A. E.; Hobbs, J. K. Nature 2004, 428, 157-160.
69. (c) Chvalun, S. N.; Shcherbina, M. A.; Yakunin, A. N.; Blackwell, J.; Percec, V. Polym. Sci. Ser. A 2007, 49, 158-167.
70. For additional examples of self-assembling amphiphilic dendrons, see: (a) Kim, C.; Kim, K. T.; Chang, Y.; Song, H. H.; Cho, T.-Y.; Jeon, H.-J. J. Am. Chem. Soc. 2001, 123, 5586-5587.
71. (b) Cho, B.-K.; Jain, A.; Gruner, S. M.; Wiesner, U. Science 2004, 305, 1598-1601.
72. (c) Cho, B.-K.; Jain, A.; Mahajan, S.; Ow, H.; Gruner, S. M.; Wiesner, U. J. Am. Chem. Soc. 2004, 126, 4070-4071.
73. For examples of functions mediated via the 3-D structures generated by self-assembling dendrons, see: (a) Percec, V.; Heck, J.; Tomazos, D.; Falkenberg, F.; Blackwell, H.; Ungar, G. J. Chem. Soc., Perkin Trans. 1 1993, 2799-2811.
74. (b) Percec, V.; Heck, J. A.; Tomazos, D.; Ungar, G. J. Chem. Soc., Perkin Trans. 2 1993, 2381-2388.
75. (c) Percec, V.; Tomazos, D.; Heck, J.; Blackwell, H.; Ungar, G. J. Chem. Soc., Perkin Trans. 2 1994, 31-44.
76. (d) Percec, V.; Ahn, C.-H.; Barboiu, B. J. Am. Chem. Soc. 1997, 119, 12978-12979.
77. (e) Percec, V.; Ahn, C.-H.; Ungar, G.; Yeardley, D. J. P.; Moller, M.; Sheiko, S. S. Nature 1998, 391, 161-164.
78. (f) Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurysamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H.-W.; Hudson, S. D.; Duan, H. Nature 2002, 419, 384-387.
79. (g) Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlund, U.; Hudson, S. D.; Heiney, P. A.; Duan, H.; Magonov, S. N.; Vinogradov, S. A. Nature 2004, 430, 764-768.
80. (h) Percec, V.; Rudick, J. G.; Peterca. M.; Wagner, M.; Obata, M.; Mitchell, C. M.; Cho, W.-D.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 15257-15264.
81. (a) Percec, V.; Kawasumi, M. Macromolecules 1991, 24, 6318-6324.
82. (b) Percec, V.; Kawasumi, M. Macromolecules 1992, 25, 3843-3850.
83. (c) Percec, V.; Chu, P. W.; Kawasumi, M. Macromolecules 1994, 27, 4441-4453.
84. (d) Percec, V.; Chu, P.; Ungar, G.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 11441-11454.
85. (a) Napolitano, E.; Giannone, E.; Fiaschi, R.; Marsili, A. J. Org. Chem. 1983, 48, 3653-3657.
86. (b) Alesso, E. N.; Tombari, D. G.; Iglesias, G. Y. M.; Aguirre, J. M. Can. J. Chem. 1987, 65, 2568-2574.
87. Zumbrunn, A. Synthesis 1998, 9, 1357-1361.
88. (a) Nystrom, R. F.; Berger, C. R. J. Am. Chem. Soc. 1958, 80, 2896-2898.
89. (b) Albrecht, W. L.; Gustafson, D. H.; Horgan, S. W. J. Org. Chem. 1972, 37, 3355-3357.
90. (a) Seeman, W.; Johnson, J. R. J. Am. Chem. Soc. 1931, 53, 711-723.
91. (b) Chan, K. S.; Zhou, X. A.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136.
92. (a) Michaelis, A.; Richter, E. Justus Liebigs Ann. Chem. 1901, 315, 26-40.
93. (b) Matsubara, H.; Seto, K. J.; Tahara, T.; Takahashi, S. Bull. Chem. Soc. Jpn. 1989, 62, 3896-3901.
94. Tong, A. J.; Yamauchi, A.; Hayashita, T.; Zhang, Z. Y.; Smith, B. D.; Teramae, N. Anal. Chem. 2001, 73, 1530-1536.
95. (a) Percec, V.; Bae, J.-Y.; Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 1066-1069.
96. (b) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447-3452.
97. McOmie, J. F. W.; Watts, M. L.; West, D. E. Tetrahedron 1968, 24, 2289-2292.
98. Tsao, M. U. J. Am. Chem. Soc. 1951, 73, 5495-5496.
99. (a) Amedio, J. C., Jr.; Sunay, U. B.; Repic, O. Synth. Commun. 1995, 25, 667-680.
100. (b) Lawrence, N. J.; Hepworth, L. A.; Rennison, D.; McGown, A. T.; Hadfield, J. A. J. Fluorine Chem. 2003, 123, 101-108.
101. Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
102. Percec, V.; Heck, J. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 591-597.
103. (a) Kwon, Y. K.; Chvalun, S.; Schneider, A. I.; Blackwell. J.; Percec, V.; Heck, J. A. Macromolecules 1994, 27, 6129-6132.
104. (b) Kwon, Y. K.; Chvalun, S.; Blackwell, J.; Percec, V.; Heck, J. A. Macromolecules 1995, 28, 1552-1558.
105. (c) Percec, V.; Rudick, J. G.; Peterca, M.; Wagner, M.; Obata, M.; Mitchell, C. M.; Cho, W.-D.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 15257-15264.
106. (d) Percec, V.; Aqad, E.; Peterca, M.; Rudick, J. G.; Lemon, L.; Ronda, J. C.; De, B. B.; Heiney, P. A.; Meijer, E. W. J. Am. Chem. Soc. 2006, 128, 16365-16372.
107. (a) Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226-1229.
108. (b) Jansen, J. F. G. A.; Meijer, E. W.; de Brabander-van den Berg, E. M. M. J. Am. Chem. Soc. 1995, 117, 4417-4418.
109. (a) Cochran, W.; Crick, F. H. C.; Vand, V. Acta. Crystallogr. 1952, 5, 581-586.
110. (b) Klug, A.; Crick, F. H. C.; Wyckoff, H. W. Acta Crystallogr. 1958, 11, 199-213.
111. (c) Cochran, W.; Crick, F. H. C. Nature 1952, 169, 234-235.
112. (d) Wilkins, M. H. F.; Stokes, A. R.; Wilson, H. R. Nature 1953, 171, 738-740.
113. (e) Franklin, R. E.; Gosling, R. G. Nature 1953, 171, 740-741.
114. (f) Klug, A. J. Mol. Biol. 2004, 335, 3-26.
115. (g) Franklin, R. E.; Klug, A. Acta Crystallogr. 1955, 8, 777-780.
116. (h) Cohen, C.; Bear, R. S. J. Am. Chem. Soc. 1953, 75, 2783-2784.
117. (a) Zimmermann, H.; Poupko, R.; Luz, Z.; Billard, J. Z. Naturforsch., A: Phys. Sci. 1985, 40, 149-160.
118. (b) Malthête, J.; Collet, A. Nouv. J. Chim. 1985, 9, 151-153.
119. (c) Levelut, A. M.; Malthete, J.; Collet, A. J. Phys. 1986, 47, 351-357.
120. (d) Malthête, J.; Collet, A. J. Am. Chem. Soc. 1987, 109, 7544-7545.
121. (e) Poupko, R.; Luz, Z.; Spielberg, N.; Zimmermann, H. J. Am. Chem. Soc. 1989, 111, 6094-6105.
122. (f) Luz, Z.; Poupko, R.; Wachtel, E. J.; Zimmermann, H.; Bader, V. Mol. Cryst. Liq. Cryst. 2003, 397, 367-377.
123. (a) Percec, V.; Dulcey, A. E.; Peterca, M.; Ilies, M.; Sienkowska, M. J.; Heiney, P. A. J. Am. Chem. Soc. 2005, 127, 17902-17909.
124. (b) Percec, V.; Dulcey, A. E.; Peterca, M.; Ilies, M.; Nummelin, S.; Sienkowska, M. J.; Heiney, P. A. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 2518-2523.
125. (c) Peterca, M.; Percec, V.; Dulcey, A. E.; Nummelin, S.; Korey, S.; Ilies, M.; Heiney, P. A. J. Am. Chem. Soc. 2006, 128, 6713-6720.
126. (d) Percec, V.; Dulcey, A. E.; Peterca, M.; Adelman, P.; Samant, R.; Balagurusamy, V. S. K.; Heiney, P. A. J. Am. Chem. Soc. 2007, 129, 5992-6002.
127. (a) Bharathi, P.; Zhao, H. D.; Thayumanavan, S. Org. Lett. 2001, 3, 1961-1964.
128. (b) Jayakumar, K. N.; Bharathi, P.; Thayumanavan, S. Org. Lett. 2004, 6, 2547-2550.
129. (c) Vutukuri, D. R.; Basu, S.; Thayumanavan, S. J. Am. Chem. Soc. 2004, 126, 15636-15637.
130. (d) Chen, Y. B.; Ambade, A. V.; Vutukuri, D. R.; Thayumanavan, S. J. Am. Chem. Soc. 2006, 128, 14760-14761.