Dendritic polyethers: Synthesis and applications

Progress in Chemistry

Volumn 18, Issue 9, 2006, Pages 1157-1180

  Li, Jingguo ^a   Meng, Chao ^a   Zhang, Xiuqiang ^a   Zhang, Lei ^a   Zhang, Afang ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Dendrimer; Dendritic polymer; Dendronized polymer; Hyperbranched polymer; Polyether

Indexed keywords

EID: 33750162353     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (172)

1. Gao C, Yan D Y, Prog. Polym. Sci., 2004, 29: 183-275
2. Tomalia D A, Baker H. J. Polymer, 1985, 17: 117-132
3. Newkome G R, Yao Z Q, Baker G R. J. Org. Chem., 1985, 50: 2003-2004
4. Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1990, 112: 7638-7647
5. Wooley K L, Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1991, 113: 4252-4261
6. Kawaguchi T, Walke K L, Wilkins C L, et al. J. Am. Chem. Soc., 1995, 117: 2159-2165
7. Flory P J. J. Am. Chem. Soc., 1952, 74: 2718-2723
8. Kim Y H. US 4 857 630, 1987
9. Kim Y H. J. Polym. Sci. Part A: Polym. Chem., 1998, 36: 1685-1698
10. Kim Y H, Webster O W. J. Am. Chem. Soc., 1990, 112: 4592-4593
11. Bauer B J, Ramzi A, Liu D. J. Polym. Sci. Part B: Polym. Phys., 2000, 38: 95-100
12. Wu H, Xu J, Liu Y, et al. J. Appl. Polym. Sci., 1999, 72: 151-163
13. Schlüter A D. Top. Curr. Chem., 1998, 197: 165-191
14. Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1990, 112: 1010-1013
15. Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1990, 112: 7638-7647
16. Fréchet J M J, Hawker C J, Philippides A E. US 5 041 516, 1991
17. Wooley K L, Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1991, 113: 4252-4261
18. Wooley K L, Hawker C J, Fréchet J M J. Polym. Mater. Sci. Eng., 1991, 235-236
19. Wooley K L, Hawker C J, Fréchet J M J, et al. Macromolecules, 1993, 26: 1514-1519
20. Gitsov I, Fréchet J M J. J. Am. Chem. Soc., 1996, 118: 3785-3786
21. Liu M, Kono K, Fréchet J M J. J. Controlled Release, 2000, 65: 121-131
22. Chow H F, Chan I Y K, Mak C C. Tetrahedron Lett., 1995, 36: 8633-8636
23. Chow H F, Chan I Y K, Mak C C, et al. Tetrahedron, 1996, 52: 4277-4290
24. Chow H F, Wang Z Y, Lau Y F. Tetrahedron, 1998, 54: 13813-13824
25. Chen K Y, Gorman C B. J. Org. Chem., 1996, 61: 9229-9235
26. Gorman C B, Parkhurst B L, Su W Y, et al. J. Am. Chem. Soc., 1997, 119: 1141-1142
27. Gorman C B. Adv. Mater., 1997, 9: 1117-1119
28. Gorman C B, Su W Y, Jiang H, et al. Chem. Commun., 1999, 877-878
29. Tyler T L, Hanson J E. Chem. Mater., 1999, 11: 3452-3459
30. Gilat S L, Adronov A, Fréchet J M J. J. Org. Chem., 1999, 64: 7474-7484
31. Weintraub J G, Parquette J R. J. Org. Chem., 1999, 64: 3796-3797
32. Balagurusamy V S K, Ungar G, Percec V, et al. J. Am. Chem. Soc., 1997, 119: 1539-1555
33. Percec V, Cho W D, Mosier P E, et al. J. Am. Chem. Soc., 1998, 120: 11061-11070
34. Percec V, Ahn C H, Cho W D, et al. J. Am. Chem. Soc., 1998, 120: 8619-8631
35. Percec V, Cho W D, Ungar G. J. Am. Chem. Soc., 2000, 122: 10273-10281
36. Ungar G, Percec V, Holerca M N, et al. Chem. Eur. J., 2000, 6: 1258-1266
37. Weintraub J G, Parquette J R. J. Org. Chem., 1999, 64: 3796-3797
38. Hecht S, Fréchet J M J. J. Am. Chem. Soc., 1999, 121: 4084-4085
39. Wuytswinkel G V, Verheyde B, Compernolle F, et al. J. Chem. Soc. Perkin Trans. 1, 2000, 1337-1340
40. Gitsov I, Fréchet J M J. J. Am. Chem. Soc., 1996, 118: 3785-3786
41. Yu D, Vladimirov N, Fréchet J M J. Macromolecules, 1999, 32: 5186-5192
42. Fréchet J M J, Gitsov I, Monteil T, et al. Chem. Mater., 1999, 11: 1267-1274
43. Leduc M R, Hayes W, Fréchet J M J. J. Polym. Sci., Part A: Polym. Chem., 1998, 36: 1-10
44. Leduc M R, Hawker C J, Fréchet J M J, et al. J. Am. Chem. Soc., 1996, 118: 11111-11118
45. Emrick T, Hayes W, Fréchet J M J. J. Polym. Sci. Part A: Polym. Chem., 1999, 37: 3748-3755
46. Gitsov I, Ivanova P T, Fréchet J M J. Macromol. Rapid Commun., 1994, 15: 387-393
47. Mecerreyes D, Dubois P, Jérôme R, et al. J. Polym. Sci. Part A: Polym. Chem., 1999, 37: 1923-1930
48. Pyun J, Tang C, Kowalewski T, et al. Macromolecules, 2005, 38: 2674-2685
49. Matyjaszewski K, Shigemoto J T, Fréchet J M J, et al. Macromolecules, 1996, 29: 4167-4171
50. Hawker C J. Acc. Chem. Res., 1997, 30: 373-382
51. Leduc M R, Hayes W, Fréchet J M J. J. Polym. Sci. Part A: Polym. Chem., 1998, 36: 1-10
52. Hawker C J, Wooley K L, Fréchet J M J. J. Chem. Soc. Perkin Trans. 1, 1993, 1287-1297
53. Wooley K L, Hawker C J, Fréchet J M J, et al. J. Am. Chem. Soc., 1993, 115: 9836-9837
54. Hawker C J, Wooley K L, Fréchet J M J. Chem. Commun., 1994, 925-926
55. Rheiner P B, Sellner H, Seebach D H. Helv. Chim. Acta, 1997, 80: 2027-2032
56. Seebach D, Rheiner P B, Greiveldinger G, et al. Top. Curr. Chem., 1998, 197: 125-164
57. Jin R H, Aida T, Inoue S. Chem. Commun., 1993, 1260-1262
58. Pollak K W, Leon J W, Fréchet J M J, et al. Chem. Mater., 1998, 10: 30-38
59. Grayson S M, Fréchet J M J. Chem. Rev., 2001, 101: 3819-3867
60. Devadoss C, Bharathi P, Moore J S. Angew. Chem. Int. Ed. Engl., 1997, 36: 1633-1635
61. Backer S D, Prinzie Y, Verheijen W, et al. J. Phys. Chem. A, 1998, 102: 5451-5455
62. Gorman C B, Hager M W, Parkhurst B L, et al. Macromolecules, 1998, 31: 815-822
63. Wooley K L, Klug C A, Tasaki K, et al. J. Am. Chem. Soc., 1997, 119: 53-58
64. Chow H F, Mak C C. J. Chem. Soc. Perkin Trans. 1, 1994, 2223-2228
65. Chow H F, Fok L F, Mak C C. Tetrahedron Lett., 1994, 35: 3547-3550
66. Chow H F, Mak C C. Tetrahedron Lett., 1996, 37: 5935-5938
67. Chow H F, Mak C C. J. Chem. Soc. Perkin Trans. 1, 1997, 91-95
68. Chow H F, Mak C C. Pure Appl. Chem., 1997, 69: 483-488
69. McGrath D V, Wu M J, Chaudhry U. Tetrahedron Lett., 1996, 37: 6077-6080
70. McElhanon J R, Wu M J, Escobar M, et al. Macromolecules, 1996, 29: 8979-8982
71. McElhanon J R, Wu M J, Escobar M, et al. J. Org. Chem., 1997, 62: 908-915
72. McElhanon J R, McGrath D V. J. Am. Chem. Soc., 1998, 120: 1647-1656
73. Junge D M, McGrath D V, Tetrahedron Lett., 1998, 39: 1701-1704
74. Seebach D, Lapierre J M, Skobridis K, et al. Angew Chem. Int. Ed. Engl., 1994, 33: 440-444
75. Seebach D, Rheiner P B, Greiveldinger G, et al. Top Curr. Chem., 1998, 197: 125-164
76. Seebach D, Lapierre J M, Greiveldinger G, et al. Helv. Chim. Acta, 1994, 77: 1673-1688
77. Murer P K, Lapierre J M, Greiveldinger G, et al. Helv. Chim. Acta, 1997, 80: 1648-1681
78. Murer P K, Seebach D. Helv. Chim. Acta, 1998, 81: 603-631
79. Greiveldinger G, Seebach D. Helv. Chim. Acta, 1998, 81: 1003-1022
80. Gorman C B, Parkhurst B L, Su W Y, et al. J. Am. Chem. Soc., 1997, 119: 1141-1142
81. Gorman C B. Adv. Mater., 1997, 9: 1117-1119
82. Schenning A P H J, Martin R E, Ito M, et al. Chem. Commun., 1998, 1013-1014
83. Jiang D L, Aida T. Nature, 1997, 388: 454-456
84. Yamago S, Furukawa M, Azuma A, et al. Tetrahedron Lett., 1998, 39: 3783-3786
85. Brewis M, Clarkson G J, Goddard V, et al. Angew. Chem. Int. Ed. Engl., 1998, 37: 1092-1094
86. Junge D M, McGrath D V. Chem. Commun., 1997, 857-858
87. Percec V, Kawasumi M. Macromolecules, 1992, 25: 3843-3850
88. Percec V, Chu P, Kawasumi M. Macromolecules, 1994, 27: 4441-4453
89. Percec V, Chu P, Ungar G, et al. J. Am. Chem. Soc., 1995, 117: 11441-11454
90. Forier B, Dehaen W. Tetrahedron, 1999, 55: 9829-9846
91. Chow H F, Mak C C. J. Org. Chem., 1997, 62: 5116-5127
92. Serroni S, Campagna S, Juris A, et al. Chim. Ital., 1994, 124: 423-427
93. Padias A B, Hall H K, Tomalia D A, et al. J. Org. Chem., 1987, 52: 5305-5312
94. Nemoto H, Wilson J G, Nakamura H, et al. J. Org. Chem., 1992, 57: 435-435
95. Allcock H R, Ravikiran R, O'Connor S J M. Macromolecules, 1997, 30: 3184-3190
96. Jayaraman M, Fréchet J M J. J. Am. Chem. Soc., 1998, 120: 12996-12997
97. Grayson M S, Fréchet J M J. J. Am. Chem. Soc., 2000, 122: 10335-10344
98. Grayson M S, Fréchet J M J. Org. Lett., 2002, 4: 3171-3174
99. Haag R, Sunder A, Stumbé J F. J. Am. Chem. Soc., 2000, 122: 2954-2955
100. Yamakawa Y, Ueda M, Nagahata R, et al. J. Chem. Soc. Perkin Trans. 1, 1998, 4135-4139
101. Boysen M M K, Elsner K, Sperling O, et al. Eur. J. Org. Chem., 2003, 4376-4386
102. Nagasaki T, Ukon M, Arimori S, et al. Chem. Commun., 1992, 608-610
103. Nagasaki T, Kimura O, Ukon M, et al. J. Chem. Soc. Perkin Trans. 1, 1994, 75-81
104. Ferruti P, Knobloch S, Ranucci E, et al. Macromol. Chem. Phys., 1998, 199: 2565-2575
105. Wróblewski S, Kopečková P, Řihová B, et al. Macromol. Chem. Phys., 1998, 199: 2601-2608
106. Mammen M, Choi S K, Whitesides G M. Angew. Chem. Int. Ed., 1998, 37: 2754-2794
107. Newkome G R, Yao Z, Baker G R, et al. J. Org. Chem., 1985, 50: 2003-2004
108. Tomalia D A, Berry V, Hall M, et al. Macromolecules, 1987, 20: 1167-1169
109. Newkome G R, Moorefield C N, Baker G R, et al. Angew. Chem. Int. Ed. Engl., 1991, 30: 1176-1778
110. Hawker C J, Wooley K L, Fréchet J M J. J. Chem. Soc. Perkin Trans. 1, 1993, 1287-1297
111. Newkome G R, Young J K, Baker G R, et al. Macromolecules, 1993, 26: 2394-2396
112. Jayaraman M, Fréchet J M J. J. Am. Chem. Soc., 1998, 120: 12996-12997
113. Hawker C J, Fréchet J M J. J. Am. Chem. Soc., 1990, 112: 7638-7647
114. Newkome G R, Moorefield C N, Vögtle F. Dendritic Molecules. Weinheim, Germany: VCH, 1996
115. Matthews O A, Shipway A N, Stoddart J F. Prog. Polym. Sci., 1998, 23: 1-56
116. Chang H T, Fréchet J M J. J. Am. Chem. Soc., 1999, 121: 2313-2314
117. Sunder A, Hanselmann R, Frey H, et al. Macromolecules, 1999, 32: 4240-4246
118. Sunder A, Krämer M, Frey H, et al. Angew. Chem. Int. Ed., 1999, 38: 3552-3555
119. Sunder A, Türk H, Frey H, et al. Macromolecules, 2000, 33: 7682-7692
120. Sunder A, Mülhaupt R, Frey H. Macromolecules, 2000, 33: 309-314
121. Knischka R, Lutz P J, Frey H, et al. Macromolecules, 2000, 33: 315-320
122. Sunder A, Bauer T, Frey H, et al. Macromolecules, 2000, 33: 1330-1337
123. Sunder A, Mülhaupt R, Frey H, et al. Macromolecules, 2000, 33: 253-254
124. Haag R, Stumbe J F, Frey H, et al. Macromolecules, 2000, 33: 8158-8166
125. Mecking S, Frey H, Sunder A, et al. Macromolecules, 2000, 33: 3958-3960
126. Slagt M Q, Stiribe Robertus S E, Frey H, et al. Macromolecules, 2002, 35: 5734-5737
127. Stiriba S E, Kautz H, Frey H. J. Am. Chem. Soc., 2002, 124: 9698-9699
128. Salazar R, Fomina L, Fomine S. Polym. Bull., 2001, 47: 151-158
129. Uhrich K E, Hawker C J, Fréchet J M J, et al. Macromolecules, 1992, 25: 4583-4587
130. Uhrich K E, Hawker C J, Fréchet J M J, et al. Polym. Mat. Sci. Eng., 1991, 64: 237-238
131. Miller T M, Nennan T X, Kwock E W. J. Am. Chem. Soc., 1993, 115: 356-357
132. Miller T M, Nennan T X, Kwock E W. Macromol. Symp., 1994, 77: 35-42
133. Mueller A, Kowalewski T, Wooley K L. Macromolecules, 1998, 31: 776-786
134. Gooden J K, Gross M L, Wooley K L, et al. J. Am. Chem. Soc., 1998, 120: 10180-10186
135. Kanoh S, Nishimura T, Mitla Y, et al. Macromolecules, 2002, 35: 651-657
136. Jayakannan M, Ramakrishnan S. Chem. Commun., 2000, 1967-1968
137. Hawker C J, Farrington P, Fréchet J M J, et al. J. Am. Chem. Soc., 1995, 117: 4409-4410
138. Emrick T, Chang H T, Fréchet J M J. Macromolecules, 1999, 32: 6380-6382
139. Emrick T, Chang H T, Fréchet J M J. J. Polym. Sci. Part A: Polym. Chem., 2000, 38: 4850-4869
140. Magnusson H, Malmstrǒm E, Hult A. Macromol. Rapid Commun., 1999, 20: 453-457
141. Magnusson H, Malmstrǒm E, Hult A. Macromolecules, 2001, 34: 5786-5791
142. Hawker C J, Chu F, Pomery P J, et al. Macromolecules, 1996, 29: 3831-3838
143. Nishimoto A, Agehara K, Furuya N, et al. Macromolecules, 1999, 32: 1541-1548
144. Wang X, Chen J, Hong L, et al. J. Polym. Sci. Part B: Polym. Phys., 2001, 39: 2225-2230
145. Komber H, Ziemer A, Voit B. Macromolecules, 2002, 35: 3514-3519
146. Yan D Y, Zhou Y F, Hou J. Science, 2004, 303: 65-67
147. Zhou Y, Yan D Y. Angew. Chem. Int. Ed., 2004, 6: 325-329
148. Huang F, Gibson H W. J. Am. Chem. Soc., 2004, 126: 14738-14739
149. Huang F, Nagvekar D S, Slebodnick C, et al. J. Am. Chem. Soc., 2005, 127: 484-485
150. Karakaya B, Claussen W, Schlüter A D, et al. J. Am. Chem. Soc., 1997, 119: 3296-3301
151. Bo Z, Schlüter A D. Chem. Eur. J., 2000, 6: 3235-3241
152. Bo Z, Zhang C, Schlüter A D, et al. Macromolecules, 2000, 33: 2688-2694
153. Desal A, Atkinson N, Hawker C J, et al. J. Polym. Sci. Part A: Polym. Chem., 2000, 38: 1033-1044
154. Cheng C X, Tang R P, Zhao Y L, et al. J. Appl. Polym. Sci., 2004, 91: 2733-2737
155. Zhuravel M A, Davis N E, Nguyen S T, et al. J. Am. Chem. Soc., 2004, 126: 9882-9883
156. Marsitzky D, Vestberg R, Carter K R, et al. J. Am. Chem. Soc., 2001, 123: 6965-6972
157. Chou C H, Shu C F. Macromolecules, 2002, 35: 9673-9677
158. Fu Y Q, Li Y, Bo Z S, et al. Macromolecules, 2004, 37: 6395-6400
159. Malenfant P R L, Fréchet J M J. Macromolecules, 2000, 33: 3634-3640
160. Apperloo J J, Malenfant P R L, Fréchet J M J, et al. J. Am. Chem. Soc., 2000, 122: 7042-7051
161. Lee M, Jeong Y S, Zin W C, et al. Chem. Eur. J., 2002, 8: 876-883
162. Kim H J, Zin W C, Lee M. J. Am. Chem. Soc., 2004, 126: 7009-7014
163. Ryu J H, Bae J, Lee M. Macromolecules, 2005, 38: 2050-2052
164. Dahan A, Portnoy M. Macromolecules, 2003, 36: 1034-1038
165. Dahan A, Portnoy M. Chem. Commun., 2002, 2700-2701
166. Dahan A, Portnoy M. Org. Lett., 2003, 5: 1197-1200
167. Dahan A, Weissberg A, Portnoy M. Chem. Commun., 2003, 1206-1207
168. Sato T, Jiang D L, Aida T. J. Am. Chem. Soc., 1999, 121: 10658-10659
169. Masuo S, Yoshikawa H, Masuhara H, et al. J. Phys. Chem. B, 2003, 107: 2471-2479
170. Vriezema D M, Aragoès M C, Elemans J A A W, et al. Chem. Rev., 2005, 105: 1445-1489
171. Kinbara K, Aida T. Chem. Rev., 2005, 105: 1377-1400
172. Madden D R. Nature Rev., 2002, 3: 91-101