Birth of a new macromolecular architecture: Dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry

Progress in Polymer Science (Oxford)

Volumn 30, Issue 3-4, 2005, Pages 294-324

  Tomalia, Donald A ^a,b  

^a Dendritic NanoTechnologies Inc   (United States)

^b CENTRAL MICHIGAN UNIVERSITY   (United States)

Author keywords

Core shell tecto(dendrimers); Dendrigrafts; Dendrimers; Dendritic polymers; Dendritic state; Dendrons; Divergent synthesis; Megamers; Nanobuilding blocks; Nanoscale synthesis; PAMAM; Poly(amidoamine)

Indexed keywords

ANISOTROPY; DNA; GRAFT COPOLYMERS; MOLECULAR STRUCTURE; NANOSTRUCTURED MATERIALS; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

CORE-SHELL TECTO (DENDRIMERS); DENDRIGRAFTS; DENDRONS; DIVERGENT SYNTHESIS; MEGAMERS; NANOBUILDING BLOCKS; NANOSCALE SYNTHESIS; POLY(AMIDOAMINE) (PAMAM);

DENDRIMERS;

EID: 18444392735     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2005.01.007     Document Type: Review

References (124)

1. P.W. Anderson More is different Science 177 1972 393 396
2. W.I. Atkinson Nanocosm: nanotechnology and the big changes coming from the inconceivably small 2003 American Management Association New York
3. National Nanotechnology Initiative Home Page. http://www.nano.gov/ (accessed Feb 2004).
4. J.M.J. Fréchet, and D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester
5. D.A. Tomalia, and J.M.J. Fréchet Discovery of dendrimers and dendritic polymers: a brief historical perspective J Polym Sci Part A Polym Chem 40 2002 2719 2728
6. D.A. Tomalia A new complexity Mater Today 6 2003 72
7. J.R. Partington A short history of chemistry 1957 Dover Publications, Inc. New York
8. H. Staudinger From organic chemistry to macromolecules 1970 Wiley-Interscience New York
9. H. Morawetz The origin and growth of a science 1985 Wiley New York
10. B. Pullman The atom in the history of human thought 1998 Oxford University Press New York
11. J. Berzelius J Fortsch Phys Wissensch 11 1832 44
12. E.J. Corey, and X.-M. Cheng The logic of chemical synthesis 1989 Wiley New York
13. E. Heilbronner, and J.D. Dunitz Reflections on symmetry 1993 VCH Publishers, Inc. New York
14. E. Buhleier, W. Wehner, and F. Vögtle Cascade - and nonskid-chain-like syntheses of molecular cavity topologies Synthesis 1978 155 158
15. P.J. Flory Principles of polymer chemistry 1953 Cornell University Press Ithaca, NY
16. J. Roovers Advances in polymer science, branched polymers ii vol. 143 2000 Springer Berlin
17. J. Scheirs W. Kaminsky Metallocene-based polyolefins vols. 1 and 2 2000 Wiley Brisbane Ltd
18. H.-G. Elias An introduction to polymer science 1997 VCH Weinheim
19. D.A. Tomalia, K. Mardel, S.A. Henderson, G. Holan, and R. Esfand Dendrimers - an enabling synthetic science to controlled organic nanostructures W.A. Goddard III Handbook of nanoscience, engineering and technology 2003 CRC Press Boca Raton, FL 1 34
20. D.S. Goodsell Biomolecules and nanotechnology Am Sci 88 2000 230 237
21. W.I. Atkinson Wet nanotech Nanocosm: nanotechnology and the big changes coming from the inconceivably small 2003. American Management Association New York p. 167-94
22. W.E. Billups M.A. Ciufolini Buckminsterfullerenes 1993 VCH Publishers, Inc. New York
23. C.F. Richardson, D.I. Schuster, and S.R. Wilson Org Lett 2 2000 1011 1014
24. D.A. Tomalia Starburst dendrimers - nanoscopic supermolecules according to dendritic rules and principles Macromol Symp 101 1996 243 255
25. A.K. Naj Persistent inventor markets a molecule Wall Street J 1996 B1
26. S. Hecht, and J.M.J. Fréchet Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science Angew Chem Int Ed 40 1 2001 74 91
27. D.A. Tomalia, A.M. Naylor, and W.A. Goddard III Starburst dendrimers: molecular level control of size, shape, surface chemistry, topology and flexibility from atoms to macroscopic matter Angew Chem Int Ed Engl 29 1990 138 175
28. J.M.J. Fréchet, C.J. Hawker, I. Gitsov, and J.W. Leon JMS Pure Appl Chem A33 1999 1399
29. B.I. Voit Acta Polym 46 1995 87 99
30. M. Fischer, and F. Vögtle Dendrimers: from design to application - a progress report Angew Chem Int Ed 38 1999 884 905
31. P.J. Flory J Am Chem Soc 74 1952 2718
32. P.A. Gunatillake, G. Odian, and D.A. Tomalia Macromolecules 21 1988 1556 1562
33. Y.H. Kim, and O.W. Webster Polym Prepr 29 1988 310
34. Y.H. Kim, and O.W. Webster J Am Chem Soc 112 1990 4592
35. T. Emrick, H.T. Chang, and J.M.J. Frèchet J Polym Sci A 38 2000 4850
36. T. Emrick, H.T. Chang, and J.M.J. Frèchet An a2+b3 approach to hyperbranched aliphatic polyethers containing chain end epoxy substituents Macromolecules 32 1999 6380 6382
37. P. Bharati, and J.S. Moore J Am Chem Soc 119 1997 3391
38. A.M. Muzafarov, E.A. Rebrov, O.B. Gorbatsevich, M. Golly, H. Gankema, and M. Moller Macromol Symp 102 1996 35
39. J.F. Miravet, and J.M.J. Frèchet Macromolecules 31 1998 3461
40. F. Chu, and C.J. Hawker Polym Bull 30 1993 265
41. C.J. Hawker, R. Lee, and J.M.J. Frechet J Am Chem Soc 113 1991 4583
42. K.E. Uhrich, C.J. Hawker, J.M.J Frèchet, and S.R Tumer Macromolecules 25 1992 4583
43. M. Liu, N. Vladimirov, and J.M.J. Frèchet A new approach to hyperbranched polymers by ring-opening polymerization of an ab monomer: 4-(2-hydroxyethyl)-e-caprolactone Macromolecules 32 1999 6881 6884
44. J.M.J. Fréchet, M. Henni, I. Gitsov, S. Aoshima, M.R. Leduc, and R.B. Grubbs Science 269 1995 1080
45. C.J. Hawker, P.J. Farrington, M.E. Mackay, K.L. Wooley, and J.M.J. Frechet J Am Chem Soc 117 1995 4409
46. Gong C, Miravet J, Frèchet JMJ. J Polym Sci A; 37:3193.
47. A. Sunder, J. Heinemann, and H. Frey Chem Eur J 6 2000 2499
48. D.A. Tomalia, D.M. Hedstrand, and M.S. Ferrito Macromolecules 24 1991 1435 1438
49. M. Gauthier, and M. Moller Macromolecules 24 1991 4548
50. R.A. Kee, M. Gauthier, and D.A. Tomalia Semi-controlled dendritic structure synthesis J.M.J. Frechet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley West Sussex 209 235
51. M. Gauthier, J. Li, and J. Dockendorff Arborescent polystyrene-graft- poly(2-vinylpyridine) copolymers as unimolecular micelles. Synthesis from acetylated substrates Macromolecules 36 2003 2642 2648
52. J.-L. Six, and Y. Gnanou Macromol Symp 95 1995 137
53. D. Taton, E. Cloutet, and Y. Gnanou Macrmol Chem Phys 199 1998 2501
54. M. Trollsas, and J.L. Hedrick Dendrimer-like star polymers J Am Chem Soc 120 1998 4644 4651
55. 2 macromonomers Macromolecules 31 1998 4390 4395
56. J. Roovers Advances in polymer science, branched polymers i vol. 142 1999 Springer Berlin
57. R.B. Grubbs, C.J. Hawker, J. Dao, and J.M.J. Frèchet Angew Chem Int Ed Engl 36 1997 270
58. Z. Guan, P.M. Cotts, E.F. McCord, and S.J. McLain Science 283 1999 2059 2062
59. Tomalia DA, Dewald JR, Hall MJ, Martin SJ, Smith PB. In: Preprints of the 1st SPSJ international polymer conference, society of polymer science, August, Kyoto, Japan; 1984.
60. D.A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, and S. Martin A new class of polymers: starburst dendritic macromolecules Polym J (Tokyo) 17 1985 117 132
61. R. Esfand, and D.A. Tomalia Laboratory synthesis of poly(amidoamine) (pamam) dendrimers J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 587 604
62. J.M.J. Fréchet, H. Ihre, and M. Davey Preparation of frechet-type polyether dendrons and aliphatic polyester dendrimers by convergent growth: an experimental primer J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 569 586
63. M.H.P. Van Genderen, M.H.A. Mak, B.D-V.D. Berg, and E.W. Mejer Synthesis and characterization of poly(propylene imine) dendrimers J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 605 616
64. D.A. Tomalia Dendrimer molecules Sci Am 272 1995 42 46
65. G.R. Newkome, C.N. Moorfield, and F. Vögtle Dendritic molecules 1996 VCH Weinheim
66. C.J. Hawker, and J.M.J. Fréchet Preparation of polymers with controlled molecular architecture. A new convergent approach to dendritic macromolecules J Am Chem Soc 112 1990 7638 7647
67. F. Zeng, and S.C. Zimmerman Chem Rev 97 1997 1681 1712
68. M.K. Lothian-Tomalia, D.M. Hedstrand, and D.A. Tomalia A contemporary survey of covalent connectivity and complexity. The divergent synthesis of poly(thioether) dendrimers. Amplified, genealogical directed synthesis leading to the de gennes dense packed state Tetrahedron 53 1997 15495 15513
69. D.A. Tomalia Starburst/cascade dendrimers: fundamental building blocks for a new nanoscopic chemistry set Aldrichim Acta 26 4 1993 91 101
70. D.A. Tomalia Starburst/cascade dendrimers: fundamental building blocks for a new nanoscopic chemistry set Adv Mater 6 1994 529 539
71. G.J. Kallos, D.A. Tomalia, D.M. Hedstrand, S. Lewis, and J. Zhou Molecular weight determination of a polyamidoamine starburst polymer by electrospray ionization mass spectrometry Rapid Commun Mass Spectrom 5 1991 383 386
72. P.R. Dvornic, and D.A. Tomalia Genealogically directed syntheses (polymerizations): direct evidence by electrospray mass spectroscopy Macromol Symp 98 1995 403 428
73. J.C. Hummelen, J.L.J. van Dongen, and E.W. Meijer Electrospray mass spectrometry of poly(propylene imine) dendrimers - the issue of dendritic purity of polydispersity Chem Eur J 3 1997 1489 1493
74. J. Peterson, V. Allikmaa, J. Subbi, T. Penk, and M. Lopp Structural deviations in poly(amidoamine) dendrimers: a maldi-tof ms analysis Eur Polym J 39 2003 33 42
75. H.M. Brothers II, L.T. Piehler, and D.A. Tomalia Slab-gel and capillary electrophoretic characterization of polyamidoamine dendrimers J Chromatogr A 814 1998 233 246
76. C. Zhang, and D.A. Tomalia Gel electrophoresis characterization of dendritic polymers J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 239 252
77. D.A. Tomalia, and J.M.J. Fréchet Introduction to the dendritic state J.M.J. Frechet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 3 44
78. Bohr N. Nobel laureate lecture. Nobel Laureate Lecture; 1922.
79. D.A. Tomalia, B. Huang, D.R. Swanson, H.M. Brothers II, and J.W. Klimash Structure control within poly(amidoamine) dendrimers: Size, shape and regio-chemical mimicry of globular proteins Tetrahedron 59 2003 3799 3813
80. J.L. Jackson, H.D. Chanzy, F.P. Booy, B.J. Drake, D.A. Tomalia, B.J. Bauer, and E.J. Amis Visualization of dendrimer molecules by transmission electron (tem): staining methods and cryo-tem of vitrified solutions Macromolecules 31 1998 6259 6265
81. R. Esfand, and D.A. Tomalia Poly(amidoamine) (pamam) dendrimers: from biomimicry to drug delivery and biomedical applications Drug Discov Today 6 8 2001 427 436
82. J.-W. Weener, M.W.P.L. Baars, and E.W. Meijer Some unique features of dendrimers based upon self-assembly and host-guest properties J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 387 424
83. D.A. Tomalia, H.M. Brothers II, L.T. Piehler, H.D. Durst, and D.R. Swanson Partial shell-filled core-shell tecto(dendrimers): a strategy to surface differentiated nano-clefts and cusps Proc Natl Acad Sci USA 99 8 2002 5081 5087
84. G.J. de A.A. Soler-Illia, L. Rozes, M.K. Boggiano, C. Sanchez, C.O. Turrin, A.M. Caminade, and J.P. Majoral New mesotextured hybrid materials made from assemblies of dendrimers and titanium (iv)-oxo-organo clusters Angew Chem Int Ed 39 2000 4250
85. D.A. Tomalia, and I. Majoros Dendrimeric supramolecular and supramacromolecular assemblies A. Ciferri Supramolecular polymers 2000 Marcel Decker New York 359 434
86. D.A. Tomalia, and I. Majoros Dendrimeric supramolecular and supramacromolecular assemblies J Macromol Sci C43 2003 411 477
87. R.M. Crooks, B. Lemon III, L. Sun, L.K. Yeung, and M. Zhao Dendrimer-encapsulated metals and semiconductors: synthesis, characterization, and applications Topics in Current Chemistry, vol. 212 2001 Springer Berlin
88. A.W. Freeman, S.C. Koene, P.R.L. Maienfant, M.E. Thompson, and J.M.J. Frèchet Dendrimer-containing light-emitting diodes: toward site-isolation of chromophores J Am Chem Soc 122 2000 12385 12386
89. M.E. Piotti, F. Rivera, R. Bond, C.J. Hawker, and J.M.J. Frèchet J Am Chem Soc 121 1999 9471
90. C. Bieniarz Dendrimers: applications to pharmaceutical and medicinal chemistry Encycl. of pharmaceutical technology 1998. Marcel Dekker New York p. 55-89
91. D.C. Tully, and J.M.J. Fréchet Chem Commun 2001 1229 1239
92. A. Adronov, and J.M.J. Fréchet Light-harvesting dendrimers Chem Commun 2000 1701 1710
93. D.-L. Jiang, and T. Aida Dendritic polymers: optical and photochemical properties J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley West Sussex 425 439
94. P. Singh, F. Moll III, S.H. Lin, and C. Ferzli Starburst dendrimers: a novel matrix for multifunctional reagents in immunoassays Clin Chem 42 9 1996 1567 1569
95. P. Singh Dendrimer-based biological reagents: preparation and applications in diagnostics J.M.J. Fréchet D.A. Tomalia Dendrimers and dendritic polymers 2001 Wiley Chichester 463 484
96. M. Nath, and C.N.R. Rao New metal disulfide nanotubes J Am Chem Soc 123 2001 4841 4842
97. M.J. O'Connell, S.M. Bachilo, C.B. Huffman, V.C. Moore, M.S. Strano, and E.H. Haroz Band gap fluorescence from individual single-walled carbon nanotubes Science 297 2002 593 596
98. Y. Zhao, B.I. Yakobson, and R.E. Smalley Dynamic topology of fullerene coalescence Phys Rev Lett 2002 185501
99. J. Li, L.T. Piehler, D. Qin, J.R. Baker Jr, and D.A. Tomalia Visualization and characterization of poly(amidoamine) dendrimers by atomic force microscopy Langmuir 16 2000 5613 5616
100. R. Yin, Y. Zhu, and D.A. Tomalia Architectural copolymers: rod-shaped, cylindrical dendrimers J Am Chem Soc 120 1998 2678 2679
101. O.A. Matthews, A.N. Shipway, and J.F. Stoddart Prog Polym Sci 23 1998 1 56
102. A.-M. Caminade, and J.-P. Majoral Chem Rev 99 1999 845
103. J.F.G.A. Jansen, E.M.M. de Brabander-van den Berg, and E.W. Meijer Encapsulation of guest molecules into a dendritic box Science 266 1994 1226 1229
104. M. Freemantle Chem Eng News April 19 1999 51 58
105. L. Balogh, D.A. Tomalia, and G.L. Hagnauer A revolution of nanoscale proportions Chem Innov 30 2000 19 26
106. D.A. Tomalia, and R. Esfand Dendrons, dendrimers and dendrigrafts Chem Ind 11 1997 416 420
107. L. Balogh, and D.A. Tomalia Poly(amidoamine) dendrimer-templated nanocomposites 1. Synthesis of zero valent copper nanosclusters J Am Chem Soc 120 1998 7355
108. Shull RD, Balogh, L, Swanson DR, Tomalia DA. Magnetic dendrimers and other nanocomposites. Book of abstracts, 216th ACS national meeting, Boston, August 23-27. Washington: MACR-069 Publisher, ACS; 1998.
109. A. Rajca, and S. Utampanya Dendrimer-based metal chelates: a new class of magnetic resonance imaging contrast agents J Am Chem Soc 115 1993 10688
110. A. Rajca, J. Wongsriratanakul, S. Rajca, and R. Cerny A dendritic macrocyclic organic polyradical with a very high spin of s=10 Angew Chem Int Ed 37 1998 1229
111. I. Tabakovic, L.L. Miller, R.G. Guan, D.C. Tully, and D.A. Tomalia Dendrimers peripherally modified with anion radicals that form pi-dimers and pi-stacks Chem Mater 9 1997 736 745
112. L.L. Miller, R.G. Duan, D.C. Tully, and D.A. Tomalia Electrically conducting dendrimers J Am Chem Soc 119 1997 1005 1010
113. M. Kawa, and J.M.J. Fréchet Self-assembled lanthanide-cored dendrimer complexes: enhancement of the luminescence properties of lanthanide ions through site-isolation and antenna effects Chem Mater 10 1998 286
114. T. Sato, D.-L. Jiang, and T. Aida A blue-luminescent dendritic rod: poly(phenyleneethynylene) within a light-harvesting dendritic envelope J Am Chem Soc 121 1999 10658 10659
115. P.G. de Gennes, and H.J. Hervet J Physique Lett (Paris) 44 1983 351 360
116. D.A. Tomalia, S. Uppuliri, D.R. Swanson, and J. Li Dendrimers as reactive modules for the synthesis of new structure controlled, higher complexity - megamers Pure Appl Chem 72 2000 2343 2358
117. J. Li, D.R. Swanson, D. Qin, H.M. Brothers II, L.T. Piehler, D.A. Tomalia, and D.J. Meier Characterization of core-shell tecto(dendrimers) molecules by tapping mode atomic force microscopy Langmuir 15 1999 7347 7350
118. S. Uppuluri, D.R. Swanson, H.M. Brothers II, L.T. Piehler, J. Li, and D.J. Meier Tecto(dendrimer) core-shell molecules: macromolecular tectonics for the systematic synthesis of larger controlled structure molecules Polym Mater Sci Eng (ACS) 80 1999 55 56
119. M. Freemantle Blossoming dendrimers Chem Eng News 77 44 1999 27 35
120. S. Uppuluri, L.T. Piehler, J. Li, D.R. Swanson, G.L. Hagnaner, and D.A. Tomalia Core-shell tecto(dendrimers): I. Synthesis and characterization of saturated shell models Adv Mater 12 11 2000 796 800
121. D.A. Tomalia, and D.R. Swanson Laboratory synthesis and characterization of megamers: core-shell tecto(dendrimers) J.M.J. Fréchet D.A. Tomalia Dendrimers and other dendritic polymers 2001 Wiley Chichester 617 629
122. M.L. Mansfield, L. Rakesh, and D.A. Tomalia The random parking of spheres on spheres J Chem Phys 105 1996 3245 3249
123. D.K. Smith Recent developments in dendrimer chemistry Tetrahedron Symposia Print 59 2003 3787 4024
124. Tomalia DA. The dendritic State. Matter Today 2005; March; 34-46.