Dendritic gelators

Topics in Current Chemistry

Volumn 256, Issue , 2005, Pages 237-273

  Hirst, Andrew R ^a   Smith, David K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Dendrimer; Gel materials; Nanotechnology; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 28944450707     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/b107178     Document Type: Article

References (146)

1. Graham T (1861) Phil Trans Roy Soc 151:183-224
2. (a) LloydDJ (1926) In: Alexander J (ed) Colloid chemistry, vol 1. Chemical Catalog Company, New York, p 767.
3. (b) Keller A (1995) Faraday Discuss 101:1-49
4. Flory PJ (1953) Principles of polymer chemistry. Cornell University Press, Ithaca, pp 347-398
5. Corriu RJP, Leclercq D (1996) Angew Chem Int Ed Engl 35:1420-1436
6. See for example: (a) Burch W, Ross Murphy SB (eds) (1988) Physical networks polymers and gels. Elsevier, London,
7. (b) Guenet J-M (1992) Thermoreversible gelation of polymers and biopolymers. Academic, London. For a general overview of self-organising polymer systems including gels in a broader context see:
8. Förster S, Konrad M (2003) J Mater Chem 13:2671-2688
9. Fages F (ed) (2005) Top Curr Chem, chapters in this volume
10. Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP (2001) Chem Rev 101:4071-4097
11. (a) Whitesides GM, Grzybowski B (2002) Science 295:2418-2421.
12. (b) Hamley IW (2003) Angew Chem Int Ed 42:1692-1712.
13. Elemans JAAW, Rowan AE, Nolte RJM (2003) J Mater Chem 13:2661-2670.
14. Schalley CA, Lützen A, Albrecht M (2004) Chem Eur J 10:1072-1080.
15. (e) Lehn J-M (2002) Proc Natl Acad Sci USA 99:4763-4768
16. Estroff LA, Hamilton AD (2004) Chem Rev 104:1201-1217
17. (a) Terech P, Weiss RG (1997) Chem Rev 97:3133-3159.
18. (b) Gronwald O, Snip E, Shinkai S (2002) Curr Opin Colloid Interface Sci 7:148-156.
19. van Esch JH, Feringa BL (2000) Angew Chem Int Ed 39:2263-2266.
20. Oda R, Hue I, Candau SJ (1998) Angew Chem Int Ed 37:2689-2691.
21. (e) Abdallah DJ, Weiss RG (2000) Adv Mater 12:1237-1247.
22. (f) Melendez RE, Carr AJ, Linton BR, Hamilton AD (2000) Struct Bond 96:31-61.
23. (g) ShimizuT (2003) Polym J 25:1-22.
24. (h) Pasini D, Kraft A (2004) Curr Opin Solid State Mater Sci 8:157-163
25. (a) NewkomeGR, Moorefield CN, Vögtle F (2001) Dendrimers and dendrons-concepts, synthesis, applications. Wiley-VCH, Weinheim,
26. (b) Fréchet JMJ, Tomalia DA (eds) (2002) Dendrimers and other dendritic polymers. Wiley, New York
27. (a) Smith DK, Hirst AR, Love CS, Hardy JG, Brignell SV, Huang B (2005) Prog Polym Sci 30:220-293.
28. (b) Smith DK, Diederich F (2000) Top Curr Chem 210:183-227.
29. Zimmerman SC, Lawless LJ (2001) Top Curr Chem 217:95-120.
30. Fréchet JMJ (2002) Proc Natl Acad Sci USA 99:4782-4787.
31. (e) Diederich F, Felber B (2002) Proc Natl Acad Sci USA 99:4778-4781.
32. (f) Gittins PJ, Twyman LJ (2003) Supramol Chem 15:5-23
33. Lee RT, Lee YC (1994) In: Lee RT, Lee YC (eds) Neoglycoconjugates: preparation and applications. Academic, San Diego, p 23
34. See for example: (a) Roy R, Zanini D, Meunier SJ, Romanowska A (1993) J Chem Soc Chem Commun 1869-1872.
35. (b) Zanini D, Roy R (1997) J Am Chem Soc 119:2088-2095
36. For an example in which dendritic branches play a steric buttressing role in controlling the self-assembly of a hexameric rosette-type aggregate see: (a) Zimmerman SC, Zeng F, Reichert DEC, Kolotuchin SV (1996) Science 271:1095-1098.
37. (b) Zeng F, Zimmerman SC, Kolotuchin SV, Reichert DEC, Ma YG (2002) Tetrahedron 58:825-843
38. For reviews of dendrimer chemistry with a significant synthetic focus see: (a)Chow H-F, Mong TK-K, Nongrum MF, Wan C-W (1998) Tetrahedron 54:8543-8660.
39. (b) Matthews OA, ShipwayAN, Stoddart JF (1998) Prog Polym Sci 23:1-56
40. Smith DK, Diederich F (1998) Chem Eur J 4:1353-1361
41. Pyun J, Zhou X-Z, Drockenmuller E, Hawker CJ (2003) J Mater Chem 13:2653-2660
42. Buhleier E, Wehner W, Vögtle F (1978) Synthesis 155-158
43. (a) Denkewalter RG, Kolc JF, Lukasavage WJ (1979) US Patent 4,360,646.
44. (b) Denkewalter RG, Kolc JF, Lukasavage WJ (1981) US Patent 4,289,872.
45. Denkewalter RG, Kolc JF, Lukasavage WJ (1983) US Patent 4,410,688
46. (a) Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) Polym J 17:117-132.
47. (b) Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1986) Macromolecules 19:2466-2468
48. Newkome GR, Yao Z, Baker GR, Gupta VK (1985) J Org Chem 50:2003-2004
49. (a) de Brabander-van den Berg EMM, Meijer EW (1993) Angew Chem Int Ed 32:1308-1311.
50. (b) Meijer EW, Bosman HJM, van den Booren HAMJ, de Brabandervan den Berg EMM, Castelijns AMCF, De Man HCJ, Reintjens RWEC, Stoelwinder CJC, Nijenhuis AJ (1996) US Patent 5,610,268
51. Wörner C, Mülhaupt R (1993) Angew Chem Int Ed 32:1306-1308
52. (a) Hawker C, Fréchet JMJ (1990) J Chem Soc Chem Commun 1010-1013.
53. (b) Hawker CJ, Fréchet JMJ (1990) J Am Chem Soc 112:7638-7647
54. Miller TM, Neenan TX (1990) Chem Mater 2:346-349
55. Moore JS, Xu Z (1991) Macromolecules 24:5893-5894
56. Grayson SM, Fréchet JMJ (2001) Chem Rev 101:3819-3867
57. (a) Wooley KL, Hawker CJ, Fréchet JMJ (1991) J Am Chem Soc 113:4252-4261.
58. (b) Kawaguchi T, Walker KL, Wilkins CL, Moore JS (1995) J Am Chem Soc 117:2159-2165.
59. Mattei S, Wallimann P, Kenda B, Amrein W, Diederich F (1997) Helv Chim Acta 80:2391-2417
60. (a) Inoue K (2000) Prog Polym Sci 25:453-571.
61. (b) Yates CR, Hayes W (2004) Eur Polym J 40:1257-1281
62. Sunder A, Hanselmann R, Frey H, Mülhaupt R (1999) Macromolecules 32:4240-4246
63. (a) Kim MK, Jeon YM, Jeon WS, Kim HJ, Hong SG, Park CG, Kim K (2001) Chem Commun 667-668.
64. (b) Wang RY, Yang J, Zheng ZP, Carducci MD, Jiao J, Seraphin S (2001) Angew Chem Int Ed 40:549-552.
65. Gopidas KR, Whitesell JK, Fox MA (2003) J Am Chem Soc 125:6491-6502.
66. Love CS, Chechik V, Smith DK, Brennan C (2004) J Mater Chem 14:919-924.
67. (e) Daniel M-C, Ruiz J, Nlate S, Biais J-C, Astruc D (2003) J Am Chem Soc 125:2617-2628.
68. (f) Wang YA, Li JJ, Chen HY, PengXG (2002) J Am Chem Soc 124:2293-2298
69. Kim Y, Mayer MF, Zimmerman SC (2003) Angew Chem Int Ed 42:1121-1126
70. (a) van Hest JCM, Delnoye DAP, Baars MWPL, van Genderen MHP, Meijer EW (1995) Science 268:1592-1595.
71. (b) van Hest JCM, Delnoye DAP, Baars MWPL, Elissen-Román C, van Genderen MHP, Meijer EW (1996) Chem Eur J 2:1616-1626
72. For reviews see: (a) Dennig J (2003) Top Curr Chem 228:227-236.
73. (b) Stiriba SE, Frey H, Haag R (2002) Angew Chem Int Ed 41:1329-1334
74. For very selected references see: (a) Percec V, Chu PW, Ungar G, Zhou JP (1995) J Am Chem Soc 117:11441-11454.
75. (b) Percec V, Cho W-D, Mosier PE, Ungar G, Yeardley DJP (1998) J Am Chem Soc 120:11061-11070.
76. Pesak DJ, Moore JS (1997) Angew Chem Int Ed Engl 36:1636-1639.
77. Lorenz K, Kolter D, Stuhn B, Mülhaupt R, Frey H (1996) Adv Mater 8:414-416.
78. (e) Baars MWPL, Sontjens SHM, Fischer HM, Peerlings HWI, Meijer EW (1998) Chem Eur J 4:2456-2466.
79. (f) Saez IM, Goodby JW (2003) Chem Eur J 9:4869-4877
80. Newkome GR, Baker GR, Saunders MJ, Russo PS, Gupta VK, Yao Z.-Q., Miller JE, Bouillion K (1986) J Chem Soc Chem Commun 752-753
81. (a) Newkome GR, Baker GR, Arai S, Saunders MJ, Russo PS, Theriot KJ, Moorefield CN, Rogers LE, Miller JE, Lieux TR, Murray ME, Phillips B, Pascal L (1990) J Am Chem Soc 112:8458-8465.
82. (b) Newkome GR, Moorefield CN, Baker GR, Behera RK, Escamilla GH, Saunders MJ (1992) Angew Chem Int Ed Engl 31:917-919.
83. Newkome GR, Lin X, Yaxiong C, Escamilla GH (1993) J Org Chem 58:3123-3129.
84. Yu KH, Russo PS, Younger L, Henk WG, Hua DW, Newkome GR, Baker G (1997) J Polym Sci Polym Phys 35:2787-2793
85. Jørgensen M, Bechgaard K, Bjørnholm T, Sommer-Larsen P, Hansen LG, Schaumburg K (1994) J Org Chem 59:5877-5882
86. Percec V, Glodde M, Bera TK, Miura Y, Shiyanovskaya I, Singer KD, Balagurusamy VSK, Heiney PA, Schnell I, Rapp A, Spiess HW, Hudson SD, Duan H (2002) Nature 419:384-387
87. Le Gall T, Pearson C, Bryce MR, Petty MC, Dahlgaard H, Becher J (2003) Eur J Org Chem 3562-3568
88. Marmillon C, Gauffre F, Gulik-Krzywicki T, Loup C, Caminade A-M, Majorai J-P, Vors J-P, Rump E (2001) Angew Chem Int Ed 40:2626-2629
89. (a) Launay N, Caminade A-M, Lahana R, Majoral J-P (1994) Angew Chem Int Ed Engl 33:1589-1592.
90. (b) Chang JY, Ji HJ, Han MJ, Rhee SB, Cheong S, Yoon M (1994) Macromolecules 27:1376-1380
91. El Ghzaoui A, Gauffre F, Caminade A-M, Majorai J-P, Lannibois-Drean H (2004) Langmuir 20:9348-9353
92. Klok H-A, Hwang JJ, Hartgerink JD, Stupp SI (2002) Macromolecules 35:6101-6111
93. Stendahl JC, Li L, Claussen RC, Stupp SI (2004) Biomaterials 25:5847-5856
94. Namazi H, Adeli M (2003) Eur Poly J 39:1491-1500
95. (a) Carnahan MA, Grinstaff MW (2001) Macromolecules 34:7648-7655.
96. (b) Carnahan MA, Middleton C, Kim J, Kim T, Grinstaff MW (2002) J Am Chem Soc 124:5291-5293.
97. Luman NR, Smeds KA, Grinstaff MW (2003) Chem Eur J 9:5618-5626
98. Gitsov I, Zhu C (2002) Macromolecules 35:8418-8427
99. Jang W-D, Jiang D-L, Aida T (2000) J Am Chem Soc 122:3232-3233
100. Jang W-D, Aida T (2003) Macromolecules 36:8461-8469
101. Jang W-D, Aida T (2004) Macromolecules 37:7325-7330
102. Zhang W, Gonzalez SO, Simanek EE (2002) Macromolecules 35:9015-9021
103. Kim C, Kim KT, Chang Y, Song HH, Cho T-Y, Jeon H-J (2001) J Am Chem Soc 123:5586-5587
104. Kim C, Lee SJ, Lee IH, Kim KT, Song HH, Jeon H-J (2003) Chem Mater 15:3638-3642
105. Love CS, Hirst AR, Chechik V, Smith DK, Brennan C, Ashworth I (2004) Langmuir 20:6580-6585
106. (a) Osterod F, Kraft A (1997) Chem Commun 1435-1436.
107. (b) Kraft A, Osterod F (1998) J Chem Soc Perkin Trans l 1019-1025
108. Mong TK-K, Niu A, Chow H-F, Wu C, Li L, Chen R (2001) Chem Eur J 7:686-699
109. Zubarev ER, Pralle MU, Sone ED, Stupp SI (2001) J Am Chem Soc 123:4105-4106
110. Zubarev ER, Stupp SI (2002) J Am Chem Soc 124:5762-5773
111. de Gans BJ, Wiegand S, Zubarev ER, Stupp SI (2002) J Phys Chem B 106:9730-9736
112. (a) Zubarev ER, Pralle MU, Sone ED, Stupp SI (2002) Adv Mater 14:198-203.
113. (b) Stendahl JC, Li LM, Zubarev ER, Chen Y-R, Stupp SI (2002) Adv Mater 14:1540-1543
114. Sone ED, Zubarev ER, Stupp SI (2002) Angew Chem Int Ed 41:1705-1709
115. Li L, Beniash E, Zubarev ER, Xiang W, Rabatic BM, Zhang G, Stupp SI (2003) Nat Mater 2:689-694
116. Messmore BW, Hulvat JF, Sone ED, Stupp SI (2004) J Am Chem Soc 126:14452-14458
117. (a) Hanabusa K, Miki T, Taguchi Y, Koyama T, Shirai H (1993) J Chem Soc Chem Commun 1382-1384.
118. (b) Jeong SW, Shinkai S (1997) Nanotechnology 8:179-185.
119. Inoue K, Ono Y, Kanekiyo Y, Ishii T, Yoshihara K, Shinkai S (1999) J Org Chem 64:2933-2937.
120. Tata M, John VT, Waguespack YY, McPherson GL (1994) J Am Chem Soc 116:9464-9470.
121. (e) Simmons BA, Taylor CE, Landis FA, John VT, McPherson GL, Schwartz DK, Moore R (2001) J Am Chem Soc 123:2414-2421.
122. (f) Willemen HM, Vermonden T, Marcelis ATM, Sudhölter EJR (2002) Langmuir 18:7102-7106.
123. (g) de Loos M, van Esch J, Kellogg RM, Feringa BL (2001) Angew Chem Int Ed 40:613-616.
124. (h) Nakano K, Hishikawa Y, Sada K, Miyata M, Hanabusa K (2000) Chem Lett 1170-1171
125. (a) Maitra U, Kumar PV, Chandra N, D'Sousa LJ, Prasanna MD, Raju AR (1999) Chem Commun 595-596.
126. (b) Friggeri A, Gronwald O, van Bommel KJC, Shinkai S, Reinhoudt DN (2002) J Am Chem Soc 124:10754-10758.
127. Babu P, Sangeetha NM, Vijaykumar P, Maitra U, Rissanen K, Raju AR (2003) Chem Eur J 9:1922-1932
128. (a) Ihara H, Sakurai T, Yamada T, Hashimoto T, Takafuji M, Sagawa T, Hachisako H (2002) Langmuir 18:7120-7123
129. (b) Dukh M, Saman D, Kroulik J, Cerny I, Pouzar V, Kral V, Drasar P (2003) Tetrahedron 59:4069-4076
130. (a) George M, Weiss RG (2003) Langmuir 19:1017-1025.
131. (b) George M, Weiss RG (2001) J Am Chem Soc 123:10393-10394
132. Partridge KS, Smith DK, Dykes GM, McGrail PT (2001) Chem Commun 319-320
133. Dykes GM, Smith DK (2003) Tetrahedron 59:3999-4009
134. Hirst AR, Smith DK, Feiters MC, Geurts HPM (2004) Langmuir 20:7070-7077
135. Hirst AR, Smith DK (2004) Langmuir 20:10851-10857
136. Hirst AR, Smith DK (2004) Org Biomol Chem 2:2965-2971
137. Huang B, Hirst AR, Smith DK Castelletto V, Hamley IW (2005) J Am Chem Soc 127:7130-7139
138. Hirst AR, Smith DK, Feiters MC, Geurts HPM (2004) Chem Eur J 10:5901-5910
139. Hirst AR, Smith DK, Feiters MC, Geurts HPM, Wright AC (2003) J Am Chem Soc 125:9010-9011
140. Enomoto M, Kishimura A, Aida T (2001) J Am Chem Soc 123:5608-5609
141. Hardy JG, Hirst AR, Smith DK, Ashworth I, Brennan C (2005) Chem Commun 385-387
142. (a) Luo X, Liu B, Liang Y (2001) Chem Commun 1556-1557.
143. (b) Yamada N, Imai T, Koyama E (2001) Langmuir 17:961-963.
144. Bhattacharya S, Krishnan-Ghosh Y (2001) Chem Commun 185-186.
145. Estroff LA, Huang JS, Hamilton AD (2003) Chem Commun 2958-2959.
146. (e) Suzuki M, Yumoto M, Kimura M, Shirai H, Hanabusa K (2004) Helv Chim Acta 87:1-10