β-环糊精类衍生物的合成及应用
|
摘要
本文主要做了以下工作：
1．概述了β-环糊精类衍生物作为色谱固定相和添加剂的合成和应用，对分离机理及协同效应进行了初步的探讨。
2．依据β-环糊精类固定相和添加剂性质及分离作用机理，设计并最终合成了20种目标产物。它们分属以下四个大的类别：
a．亲油性烷基化β-环糊精五种，建立了全烷基β-环糊精的新的合成方法，大大缩短了合成的时间，取得了较高的纯度和产率。
b．亲水性β-环糊精二种，采用了较新报道的合成方法。
c．氨基酸衍生化β-环糊精八种。以β-环糊精为母体的一取代衍生物二种。以七(2，6-二-O-甲基)-β-环糊精物为母体的一取代衍生六种本系列衍生物在色谱应用方面的合成和应用未见报道。
d．二聚、交聚β-环糊精五种，本系列衍生物在色谱应用方面的合成和应用未见报道。
云南师范人学硕士研究生学位论丈6－环糊精类衍生物的合成及应用
一
注：SP为“色谱固定相”之代表缩写符号，MA为“色谱流动相添加剂”之缩写符号。
本文对所合成的目标产物用薄层层析、经典柱色谱、高效液相色谱、毛细管
电泳及红外等手段进行了提纯和表征，测定了它们的熔点。
3．所合成的目标产物分别在气相色谱、液相色谱及毛细管电泳上进行了应用，
经过初步的色谱性能研究，在己测试的部分衍生物中，各类都显示了良好的色
谱性能。能分离手性化合物包括全甲基p－环糊精、全戊基p－环糊精、磺酸化－
日．环糊精、竣甲基－日－环糊精、二酚氯聚p－环糊精，氨基酸衍生化类日－环糊精
在分离含苯环的位置异构体时初步显现了独特的分离能力，特别是在协同效应的
研究上取得了良好的效果，实现了合成的预期成果。
The main works of the thesis are as follows:
1. The development of P -cyclodextrin derivatives in chromatographic analysis was reviewed. Those chromatographic techniques included gas chromatograph,high performance liquid chromatography and capillary electrophoresis.
2. Four series of P -cyclodextrin derivaties were synthesizrd and confirmed. (l)Five alkylated P -cyclodextrins were synthesized included:
Heptakis (2,3,6-tri-O-methyl)- 3 -CD,
Heptakis (2,3,6-tri-O-ethyl)- P - CD,
Haptakis (2,3,6-tri-O-butyl)- P - CD,
Heptakis (2,3,6-tri-O-octyl)- P - CD,
Heptakis (2,6-di-O-methyl)- P - CD.
The peralkylated P - CDs were synthesized by single-step procedure.
(2) Two kinds of water-soluble P -cyclodextrin derivatives were Sulfonate P -CD and Heptakis (2,6-carboxyl)- P -CD .
(3) Eight P -cyclodextrin derivatives which were derivated with amino acids were:
Mono-O-(N-benzoyl-DL-lactamyl)- P -CD, Mono-O-(N-benzoyl-DL- valineyl)- P -CD,
3-mono-O-(N-benzoyl-DL-glycineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL-lactamyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL-valineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-L-lactamyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-L-valineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL- a -amino-butyl)-heptakis(2,6-di-O-methyl)- P -CD
(4) Five kinds of briadged and polymerized P -CD derivatives included: Oxalyl choride polymerized P -CD,
Oxalyl methyl choride polymerized 3 -CD, Oxalyl choride briadged heptakis(2,6-di-O-methyl)- 3 -CD, Tolylene 2,6-diisocyanate polymerized 3 -CD, Tolylene 2,6-diisocyanate briadged heptakis(2,6-di-O-methyl)- 3 -CD. S.Chromatographic character of 3 - CD derivatives were studied.
1．概述了β-环糊精类衍生物作为色谱固定相和添加剂的合成和应用，对分离机理及协同效应进行了初步的探讨。
2．依据β-环糊精类固定相和添加剂性质及分离作用机理，设计并最终合成了20种目标产物。它们分属以下四个大的类别：
a．亲油性烷基化β-环糊精五种，建立了全烷基β-环糊精的新的合成方法，大大缩短了合成的时间，取得了较高的纯度和产率。
b．亲水性β-环糊精二种，采用了较新报道的合成方法。
c．氨基酸衍生化β-环糊精八种。以β-环糊精为母体的一取代衍生物二种。以七(2，6-二-O-甲基)-β-环糊精物为母体的一取代衍生六种本系列衍生物在色谱应用方面的合成和应用未见报道。
d．二聚、交聚β-环糊精五种，本系列衍生物在色谱应用方面的合成和应用未见报道。
云南师范人学硕士研究生学位论丈6－环糊精类衍生物的合成及应用
一
注：SP为“色谱固定相”之代表缩写符号，MA为“色谱流动相添加剂”之缩写符号。
本文对所合成的目标产物用薄层层析、经典柱色谱、高效液相色谱、毛细管
电泳及红外等手段进行了提纯和表征，测定了它们的熔点。
3．所合成的目标产物分别在气相色谱、液相色谱及毛细管电泳上进行了应用，
经过初步的色谱性能研究，在己测试的部分衍生物中，各类都显示了良好的色
谱性能。能分离手性化合物包括全甲基p－环糊精、全戊基p－环糊精、磺酸化－
日．环糊精、竣甲基－日－环糊精、二酚氯聚p－环糊精，氨基酸衍生化类日－环糊精
在分离含苯环的位置异构体时初步显现了独特的分离能力，特别是在协同效应的
研究上取得了良好的效果，实现了合成的预期成果。
The main works of the thesis are as follows:
1. The development of P -cyclodextrin derivatives in chromatographic analysis was reviewed. Those chromatographic techniques included gas chromatograph,high performance liquid chromatography and capillary electrophoresis.
2. Four series of P -cyclodextrin derivaties were synthesizrd and confirmed. (l)Five alkylated P -cyclodextrins were synthesized included:
Heptakis (2,3,6-tri-O-methyl)- 3 -CD,
Heptakis (2,3,6-tri-O-ethyl)- P - CD,
Haptakis (2,3,6-tri-O-butyl)- P - CD,
Heptakis (2,3,6-tri-O-octyl)- P - CD,
Heptakis (2,6-di-O-methyl)- P - CD.
The peralkylated P - CDs were synthesized by single-step procedure.
(2) Two kinds of water-soluble P -cyclodextrin derivatives were Sulfonate P -CD and Heptakis (2,6-carboxyl)- P -CD .
(3) Eight P -cyclodextrin derivatives which were derivated with amino acids were:
Mono-O-(N-benzoyl-DL-lactamyl)- P -CD, Mono-O-(N-benzoyl-DL- valineyl)- P -CD,
3-mono-O-(N-benzoyl-DL-glycineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL-lactamyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL-valineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-L-lactamyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-L-valineyl)-heptakis(2,6-di-O-methyl)- P - CD, 3-mono-O-(N-benzoyl-DL- a -amino-butyl)-heptakis(2,6-di-O-methyl)- P -CD
(4) Five kinds of briadged and polymerized P -CD derivatives included: Oxalyl choride polymerized P -CD,
Oxalyl methyl choride polymerized 3 -CD, Oxalyl choride briadged heptakis(2,6-di-O-methyl)- 3 -CD, Tolylene 2,6-diisocyanate polymerized 3 -CD, Tolylene 2,6-diisocyanate briadged heptakis(2,6-di-O-methyl)- 3 -CD. S.Chromatographic character of 3 - CD derivatives were studied.
引文
1. J. Szejtli. Cyclodextrins and Their Inclusion, Budapest: Akademina Kiado, 1982:11
2. P. Croft, R. A. Bartsch. Tetrahedron, 1983, 39(9): 1417
3. A. R. Khan, P. F. orgo, K.J. Stine, V. T. D'Souza. Chem. Rew, 1998, 98(5): 1799
4．童林荟．环糊精化学-基础与应用．北京：科学出版社，2001
5. a) L. Kandra, A. Liptik, I. Jodal, P. Nanasi, J. Szejtli. J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1984, 2:869 b) J. Szejtli, L. Kandra, J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1987, 5:639
6. L. Jicsinszky, E. Fenyvesi, H. Hashimoto, A. Ueno. Comprehensive Supramolecular Chemistry, J. L. Atwood, J.-M. Lehn, Eds., Vol. 3, Cyclodextrins, Chapter 4, Pergamon: Oxford, U. K., 1996:58
7. K. Takahashi, K. Hattori, F. Toda. Tetrahedron Lett, 1984, 25:3331
8. K. Fujita, S. Nagamura, T. Imoto. Tetrahedron Lett, 1984, 25:5673
9. S. Onozuka, M. Kojima, K. Hattori, F. Toda. Buii. Chem. Soc. Jpn, 1980, 53:3221
10. R. J. Boger, R. J. Corcoran, J-M. Lehn. Helv. Chim. Acta, 1987, 61:2190
11. A. R. Khan, L. Barton, V. T. D'Souza. J. Chem. Soc. Chem. Commun. 1992, 1112
12. D. Bradley'. J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1992, 14:357
13. P. R. Ashton, S. E. Boyd, G. Gattuso, E. Y. Hartwell, R. Koniger, N. Spencer, J. F. Stoddart. J. Org. Chem., 1995, 60:3898
14. N.Sakairi, H. Kuzuhara, Chem. Lett, 1993, 1093
15. D. Sand. Anal. Chem, 1961, 34:482
16. H. Schlenk, J.L. Gellerman, D. M.Sand. Anal. Chem, 1962, 35:1529
17. B. Casu, M. Regglani. Carbohydr. Res, 1979, 76:59
18. E. Emolkava. J. Chromatogr, 1982, 251:3
19. J. Marz, L. Feltl, E. Smolková-keulemansova. J. Chromatogr, 1984, 286:17
20. M. Tanata. Anal. Chem, 1983, 36:54
21. T. Koscielski, D. Sybilska, J. Jurczak. J. Chromatogr, 1986, 364:299
22. T. Koscielski, D. Sybilska, S. Belniak, J. Jurczak. Chromatogarphia, 1984, 19:292
23. D. W. Armstrong, W. Demond. J. Chromatogr. Sci., 1984, 22:411
24. T. Koscielski, Sybilska, S. Belniak, J. Jurcza.. Chromatogarphia., 1986, 21:413
25. R. V. Vigalok, Usp. Gaz. Chromatogr. 1981, 6:190
26. C. Bichi, G. Artuffo, A. D. Amato, G. M. Nano. J HRC, 1991, 14:301
27. W. Keim, A. Khne, W. Meltzow. J HRC, 1991, 14:507
28．万宏等，分析化学，1990，20(4)：394
29. W. A. Knig, S.Lutz. J HRC & CC, 1988, 11:506
30. H-G. Schmarr. J HRC, 1990,14:207
31. W. Y. Li, H.L. Jin, D. W. Armstrong. J. Chromatogr, 1990, 509:303
32. D. W. Armstrong, W. Li. Anal. Chem., 1990,62:214
33. V. Schurig. J HRC, 1990, 13:470
34. C. Bicchi, G. Artuffo, D. W. Armstrong. J HRC, 1991, 14:701
35. A.Dietrich. J HRC, 1992, 15:176
36. W. A. Knig, S. Lutz, P. Evers. J. Chromatogr. 1990, 503:256
37. D. W. Armstrong, W. Li, A. M. Stalcup. Anal. Chim. Acta, 1990, 234:365
38. W. A. Knig. J HRC, 1992, 151:367
39. W. A. Knig, R. Krebber, P. Mischnick. J HRC, 1989, 12:732
40. W. A. Knig, P. Evers, R. Krebber, S. Schulz, C. Fehr, G. Ohloff. Tetrahedron, 1989, 45: 7003
41. V. Schurig, V. Schurig, Z. Juvanez, G. J. Nicholson, D. Schmalzing. J HRC, 1991, 14:58
42. V. Schurig. J HRC, 1990, 13:713
43. G. Alexander, Z. Juvanez, J.Szejtli. J HRC, 1988, 11:110
44. A.Venema, P. J. A. Tolsma. J HRC, 1989, 12:32
45. N.P. Nowotny, D.Schmalzing. J HRC, 1989, 12:383
46. R.Fellous. J HRC, 1990, 13:785
47. E.Guichard. J HRC, 1990, 13:299
48. G.Takebka. J HRC, 1990, 13: 202
49. W. Walther, W. Walther, M. Cereghetti. J HRC, 1991, 14:57
50. W. A.Knig. Angew. Chew, 1988, 100:989
51. W. A.Knig, S. Lutz, M. Hagen, R. Krebber. J HRC, 1989, 12:35
52. V. Schugig, H .P. Nowotny, M. Schleimer, D. Schmalzing. J HRC, 1989, 12:594
53. W. A. Knig. Carbohydr. Res. 1989, 192:51
54．万宏，董运宇，欧庆瑜．色谱，1991，9(4)：214
55. A. Venema, H. Henderiks, R.V. Geest. J HRC, 1991, 14:676
56. W. A. Knig, S. Lutz, P. Mischnick-Lubbecke, B. Brassat. J. Chromatogr, 1988, 447:193
57. W. A .Knig. J HRC, 1990, 13:328
58. W. A. Knig, R.Krebbe. J HRC, 1989, 12:641
59. W. Boland, W. Boland, W.A. Knig, R. Krebber, P.G. Mucler. Helv. Chem. Acta, 1989, 72:1288
60. W. A. Knig, D. Lcheln, T. Runge, B. Pfaffenberger. J HRC, 1991, 14:530
61. A. Mosandl, U.Hener, L.Hagenauer-Hener, A. Kusterman, J HRC & CC, 1989, 12:532
62. H-G. Schmarr. Chromatogarphia, 1990, 29:125
63. H-G. Schmarr, B. Maas, A. Mosandl. J HRC, 1991, 14:317
64. 金恒亮, D.W. Armstrong. 色谱, 1991,9(3):148
65. D. W. Armstrong, Y. Tang, J. Zukowski. Anal. Chim, 1991, 63:2858
66. D. W. Armstrong, C-D. Chang, W. Li.. J. Agric. Food. Chem, 1990,38:1674
67. A. Berthod. Carbohydr. Res. 1990, 201:175
68. D. W. Armstrong, W. Li, C-D. Chang. Anal. Chim, 1990, 62:914
69. D. W. Armstrong, H.L. Jin. J. Chromatogr, 1990, 502:154
70. W. Blum. J HRC, 1990, 13:515
71. W. A, Knig. J HRC, 1990, 13: 702
72. W. A. Knig, R. Krebber, P. Mischnick. J HRC, 1989, 12:732
73．吴宁生．色谱，1992，10：25
74．陆懋荪，于东海，阎长泰．色谱，1989，7：33
75. D. Sybilska, J.Kowalczyk, M.Asztemborska, T. Stankiewicz, J.Jurczak. J. Chromatog, 1991, 543:397-405
76. A.W. Coleman. J. Chromatog, 1988, 450:175
77. J. Debowski, D. Sybilska, J. Jurczak. J Chromatogr, 1983, 282:83
78. S. Terabe, K. Otsuka, H. Nishi. J Chromatogr, 1994, 666:295
79. H. Nishi, S. Terabe. J Chromatogr, 1995, 694:245
80. Zhu Xiao-feng, Lin Bingcheng. Chin J Chromatog, 1999, 17(2): 153
81．陈慧，王琴孙．色谱，1999，17(6)：533
82. D. W. Armstrong, W. Demond. Chromatogr. Sci, 1984, 22:411
83. D. W. Armstrong. J. Inclusion Phenom, 1984, 2:533
84. T.E. Beesley. Am. Lab, 1985, 17(5): 78
85. D. W. Armstrong. J Liq Chromatogr, 1984, 353: 7(s-2)
86. K. G. Feitsma, B. F. H. Drenth, R. A. Dezeeuw. J HRC & CC, 1984, 7:147
87. D. W. Armstrong, T. J. Ward, A. Czech, B. P. Czech, R. A. Bartsch. Anal. Chem, 1985,50:5556
88．金恒亮，D. W. Armstrong. 色谱，1990，8：8
89. D. W. Armstrong, W. Demond, B. P. Czech. Anal. Chem, 1985, 57:481
90. D. W. Armstrong, T. J. Ward, R. D. Armstrong, T. E. Beesley. Science, 1986, 232:1132
91. D. W. Armstrong, S. M. Han, Y. I. Han. Anal. Biochem, 1987, 167:261
92. S. M. Han, D.W. Armstrong. J Chromatogr, 1987, 389:256
93. P. Macaudiere, M. Caude, R. Rosset, A. Tambute. J Chromatogr, 1987, 405:135
94. J. H. Maguire. J Chromatogr, 1987, 387:453
95. K. G. Feitsma, B. H. Drenth, R. A. Dezeeuw. J Chromatogr, 1987, 387:447
96. J. I. Seeman, H. V. Secor. Anal. Chem, 1988, 60:2120
97. D. W. Armstrong, S.M. Han, Y. I. Han. Anal. Chim. Acta, 1988,208:275
98. S. M. Han, H. I. Han, D. W. Armstrong. J Chromatogr, 1988, 441:376
99．旷昌渝，吴邦桂，周竞先．色谱，1989，7：21
100．金恒亮，D. W. Armstrong. 色谱，1989，7：204
101．金恒亮，D. W. Armstrong. 色谱，1989，8：8
102. J. Haginaka, J. Wakai. Anal. Chem, 1990, 62:997
103. A. M. Stalcup, H. L. Jin, D. W. Armstrong. J Chromatogr, 1990, 499:627
104. G. Vigh, G. Quintero, G. Farkas. J Chromatogr, 1990, 506:481
105．黄天宝，旷昌渝，周竞先，苟大明．色谱．1991，19：687
106. J. Florance, Z. Konteatis. J Chromatogr, 1991,543:299
107. S. Li, W.C. Purdy. J Chromatogr, 1991, 543:105
108. D. W. Armstrong, X. P. Yang, S. M. Han, R. A. Menges. Anal Chem, 1987, 59:2594
109. A. M. Stalcup, H. L. Jin, D. W. Armstrong. J. Liq. Chromatogr, 1990, 13:473
110. M.Tanaka, T. Shono, D. Zhu. J. Chromatogr, 1984, 301: 429
111. K. Fujimura, M. Kitagawa, H. Takayanagi, T. Anclo. J. Liq. Chromatogr, 1986, 9:607
112. D. W. Armstrong, A. M. Stalcug, M. L. Hilton, J. D. Dunlan, J. R. Faulkner. J Chromatogr, 1990, 62:1610
113. D. W. Armstrong, C-D. Chang, S.H. Lee. J Chromatogr, 1991, 539:83
114. A. M. Stalcup, C-D. Chang, D. W. Armstrong. J Chromatogr, 1991, 540:113
115. M. G. Cikalo, K. D. Bartle, M. M. Robson. Analyst, 1998, 123(7): 87R
116. F. Lelieve, C.Yan, R. N. Zare, B. Gaveil. J Chromatogr, 1996, 723:145
117. D. W. Armstrong, W. Demond. J Chromatogr. Sci, 1984, 22:411
118. W. Wei, G.A. Luo, R. Xiang. J Microcol Sep, 1999, 11(4): 263
119. D. W. Armstrong, Y. Tang, T. Ward. Anal chem, 1993, 65:1114
120. S. Li, D. K. Lloyd. J Chromatogr, 1994, 666:321
121. D. Wistuba, H. Czesla, M. Roeder, V. Schurig. J Chromatogr, 1994, 38:381
122．阮宗琴，尤进茂，李菊白，欧庆瑜．色谱，2000，18(2)：183
123. X. Y. Shi, Y. Q. Zhang, J. H. Han, R. N. Fu. J Chromatogr, 2000, 52:200
124. a) I. Sugiura, M. Komiyama, N. Toshima, H. Hirai. Bull. Chem. Soc. Jpn, 1989, 62(5): 1643 b) M. Komiyama, H. Hirai. Polym. 1987, 19:773 c) M. Komiyama, I. Sugiura, H. Hirai. J Coord. Chem., 1988, 18:181
125. E. Gil-Av, B. Febush, Bosita Charles-Sigler. Tetrahedron Lett, 1966:1009
126. E. Gil-Av, B. Febush. Tetrahedron Lett, 1967:3345
127. J. L. Ge. J Microcol. Sep, 1991, 3:211
128. H. Frank, G. J. Nicholson, E. Bayer. J. Chromatogr, 1977, 15:174
129. H. Frank, G. J. Nicholson, E. Bayer. Angew. Chem., 1978, 90:396
130. Dai Rongji, Zhang Shu, Li Fang. Acta Chim Sin, 1998, 56:594
131．冯钰锜，谢敏杰，达式禄．色谱，1999，20(11)：1708
132．冯钰锜，达式禄．色谱，2000，18(3)：224
133. I. Bako, L. Jicsinzky. J Jic. Phenom, 1994, 18:275
134. W. Zhou, R. Fu, R. Dai, Z. Huang, Y. Chen. HRC, 1994, 17:719
135. S. Li, W.C. Purdy. Anal. Chem, 1992, 64:1405
136. O. Guo, T. Ren, Y. Fang, Y. Liu. J Jic. Phenom, 1995, 22:251
137. B. Hosangadi, A. Asgaonkar. J. Jic. Phenom, 1995, 23:35
138. A. Berthod, W.Y. Li, D.W. Armstrong, Anal. Chem, 1992, 64:873
139. W. Dougherty, F. Liotta, D. Mondimore, W. Shum. Tetrahedron Lett, 1990, 30:4389
140. C. Bicchi, G.Artuffo, A. D'Amato, P. Evens. HRC, 1991, 14:701
141. A. Zhang, Z. J. Gong, J. Deng, H. Liu. J Chromatogr, 1990, 521:128
142. K. Kano, T. Ishimura, S. Negi. J. Jic. Phenom, 1995,22:285
143．顾峻岭，傅若农，分析化学，2001，9：1098
144．戴荣继．特殊选择性气相色谱手性固定相的合成及性能研究：[博士论文]．北京：北京理工大学化工与材料学院，1994
2. P. Croft, R. A. Bartsch. Tetrahedron, 1983, 39(9): 1417
3. A. R. Khan, P. F. orgo, K.J. Stine, V. T. D'Souza. Chem. Rew, 1998, 98(5): 1799
4．童林荟．环糊精化学-基础与应用．北京：科学出版社，2001
5. a) L. Kandra, A. Liptik, I. Jodal, P. Nanasi, J. Szejtli. J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1984, 2:869 b) J. Szejtli, L. Kandra, J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1987, 5:639
6. L. Jicsinszky, E. Fenyvesi, H. Hashimoto, A. Ueno. Comprehensive Supramolecular Chemistry, J. L. Atwood, J.-M. Lehn, Eds., Vol. 3, Cyclodextrins, Chapter 4, Pergamon: Oxford, U. K., 1996:58
7. K. Takahashi, K. Hattori, F. Toda. Tetrahedron Lett, 1984, 25:3331
8. K. Fujita, S. Nagamura, T. Imoto. Tetrahedron Lett, 1984, 25:5673
9. S. Onozuka, M. Kojima, K. Hattori, F. Toda. Buii. Chem. Soc. Jpn, 1980, 53:3221
10. R. J. Boger, R. J. Corcoran, J-M. Lehn. Helv. Chim. Acta, 1987, 61:2190
11. A. R. Khan, L. Barton, V. T. D'Souza. J. Chem. Soc. Chem. Commun. 1992, 1112
12. D. Bradley'. J. Inclusion Phenomena and Molecular Recognition in Chemistry, 1992, 14:357
13. P. R. Ashton, S. E. Boyd, G. Gattuso, E. Y. Hartwell, R. Koniger, N. Spencer, J. F. Stoddart. J. Org. Chem., 1995, 60:3898
14. N.Sakairi, H. Kuzuhara, Chem. Lett, 1993, 1093
15. D. Sand. Anal. Chem, 1961, 34:482
16. H. Schlenk, J.L. Gellerman, D. M.Sand. Anal. Chem, 1962, 35:1529
17. B. Casu, M. Regglani. Carbohydr. Res, 1979, 76:59
18. E. Emolkava. J. Chromatogr, 1982, 251:3
19. J. Marz, L. Feltl, E. Smolková-keulemansova. J. Chromatogr, 1984, 286:17
20. M. Tanata. Anal. Chem, 1983, 36:54
21. T. Koscielski, D. Sybilska, J. Jurczak. J. Chromatogr, 1986, 364:299
22. T. Koscielski, D. Sybilska, S. Belniak, J. Jurczak. Chromatogarphia, 1984, 19:292
23. D. W. Armstrong, W. Demond. J. Chromatogr. Sci., 1984, 22:411
24. T. Koscielski, Sybilska, S. Belniak, J. Jurcza.. Chromatogarphia., 1986, 21:413
25. R. V. Vigalok, Usp. Gaz. Chromatogr. 1981, 6:190
26. C. Bichi, G. Artuffo, A. D. Amato, G. M. Nano. J HRC, 1991, 14:301
27. W. Keim, A. Khne, W. Meltzow. J HRC, 1991, 14:507
28．万宏等，分析化学，1990，20(4)：394
29. W. A. Knig, S.Lutz. J HRC & CC, 1988, 11:506
30. H-G. Schmarr. J HRC, 1990,14:207
31. W. Y. Li, H.L. Jin, D. W. Armstrong. J. Chromatogr, 1990, 509:303
32. D. W. Armstrong, W. Li. Anal. Chem., 1990,62:214
33. V. Schurig. J HRC, 1990, 13:470
34. C. Bicchi, G. Artuffo, D. W. Armstrong. J HRC, 1991, 14:701
35. A.Dietrich. J HRC, 1992, 15:176
36. W. A. Knig, S. Lutz, P. Evers. J. Chromatogr. 1990, 503:256
37. D. W. Armstrong, W. Li, A. M. Stalcup. Anal. Chim. Acta, 1990, 234:365
38. W. A. Knig. J HRC, 1992, 151:367
39. W. A. Knig, R. Krebber, P. Mischnick. J HRC, 1989, 12:732
40. W. A. Knig, P. Evers, R. Krebber, S. Schulz, C. Fehr, G. Ohloff. Tetrahedron, 1989, 45: 7003
41. V. Schurig, V. Schurig, Z. Juvanez, G. J. Nicholson, D. Schmalzing. J HRC, 1991, 14:58
42. V. Schurig. J HRC, 1990, 13:713
43. G. Alexander, Z. Juvanez, J.Szejtli. J HRC, 1988, 11:110
44. A.Venema, P. J. A. Tolsma. J HRC, 1989, 12:32
45. N.P. Nowotny, D.Schmalzing. J HRC, 1989, 12:383
46. R.Fellous. J HRC, 1990, 13:785
47. E.Guichard. J HRC, 1990, 13:299
48. G.Takebka. J HRC, 1990, 13: 202
49. W. Walther, W. Walther, M. Cereghetti. J HRC, 1991, 14:57
50. W. A.Knig. Angew. Chew, 1988, 100:989
51. W. A.Knig, S. Lutz, M. Hagen, R. Krebber. J HRC, 1989, 12:35
52. V. Schugig, H .P. Nowotny, M. Schleimer, D. Schmalzing. J HRC, 1989, 12:594
53. W. A. Knig. Carbohydr. Res. 1989, 192:51
54．万宏，董运宇，欧庆瑜．色谱，1991，9(4)：214
55. A. Venema, H. Henderiks, R.V. Geest. J HRC, 1991, 14:676
56. W. A. Knig, S. Lutz, P. Mischnick-Lubbecke, B. Brassat. J. Chromatogr, 1988, 447:193
57. W. A .Knig. J HRC, 1990, 13:328
58. W. A. Knig, R.Krebbe. J HRC, 1989, 12:641
59. W. Boland, W. Boland, W.A. Knig, R. Krebber, P.G. Mucler. Helv. Chem. Acta, 1989, 72:1288
60. W. A. Knig, D. Lcheln, T. Runge, B. Pfaffenberger. J HRC, 1991, 14:530
61. A. Mosandl, U.Hener, L.Hagenauer-Hener, A. Kusterman, J HRC & CC, 1989, 12:532
62. H-G. Schmarr. Chromatogarphia, 1990, 29:125
63. H-G. Schmarr, B. Maas, A. Mosandl. J HRC, 1991, 14:317
64. 金恒亮, D.W. Armstrong. 色谱, 1991,9(3):148
65. D. W. Armstrong, Y. Tang, J. Zukowski. Anal. Chim, 1991, 63:2858
66. D. W. Armstrong, C-D. Chang, W. Li.. J. Agric. Food. Chem, 1990,38:1674
67. A. Berthod. Carbohydr. Res. 1990, 201:175
68. D. W. Armstrong, W. Li, C-D. Chang. Anal. Chim, 1990, 62:914
69. D. W. Armstrong, H.L. Jin. J. Chromatogr, 1990, 502:154
70. W. Blum. J HRC, 1990, 13:515
71. W. A, Knig. J HRC, 1990, 13: 702
72. W. A. Knig, R. Krebber, P. Mischnick. J HRC, 1989, 12:732
73．吴宁生．色谱，1992，10：25
74．陆懋荪，于东海，阎长泰．色谱，1989，7：33
75. D. Sybilska, J.Kowalczyk, M.Asztemborska, T. Stankiewicz, J.Jurczak. J. Chromatog, 1991, 543:397-405
76. A.W. Coleman. J. Chromatog, 1988, 450:175
77. J. Debowski, D. Sybilska, J. Jurczak. J Chromatogr, 1983, 282:83
78. S. Terabe, K. Otsuka, H. Nishi. J Chromatogr, 1994, 666:295
79. H. Nishi, S. Terabe. J Chromatogr, 1995, 694:245
80. Zhu Xiao-feng, Lin Bingcheng. Chin J Chromatog, 1999, 17(2): 153
81．陈慧，王琴孙．色谱，1999，17(6)：533
82. D. W. Armstrong, W. Demond. Chromatogr. Sci, 1984, 22:411
83. D. W. Armstrong. J. Inclusion Phenom, 1984, 2:533
84. T.E. Beesley. Am. Lab, 1985, 17(5): 78
85. D. W. Armstrong. J Liq Chromatogr, 1984, 353: 7(s-2)
86. K. G. Feitsma, B. F. H. Drenth, R. A. Dezeeuw. J HRC & CC, 1984, 7:147
87. D. W. Armstrong, T. J. Ward, A. Czech, B. P. Czech, R. A. Bartsch. Anal. Chem, 1985,50:5556
88．金恒亮，D. W. Armstrong. 色谱，1990，8：8
89. D. W. Armstrong, W. Demond, B. P. Czech. Anal. Chem, 1985, 57:481
90. D. W. Armstrong, T. J. Ward, R. D. Armstrong, T. E. Beesley. Science, 1986, 232:1132
91. D. W. Armstrong, S. M. Han, Y. I. Han. Anal. Biochem, 1987, 167:261
92. S. M. Han, D.W. Armstrong. J Chromatogr, 1987, 389:256
93. P. Macaudiere, M. Caude, R. Rosset, A. Tambute. J Chromatogr, 1987, 405:135
94. J. H. Maguire. J Chromatogr, 1987, 387:453
95. K. G. Feitsma, B. H. Drenth, R. A. Dezeeuw. J Chromatogr, 1987, 387:447
96. J. I. Seeman, H. V. Secor. Anal. Chem, 1988, 60:2120
97. D. W. Armstrong, S.M. Han, Y. I. Han. Anal. Chim. Acta, 1988,208:275
98. S. M. Han, H. I. Han, D. W. Armstrong. J Chromatogr, 1988, 441:376
99．旷昌渝，吴邦桂，周竞先．色谱，1989，7：21
100．金恒亮，D. W. Armstrong. 色谱，1989，7：204
101．金恒亮，D. W. Armstrong. 色谱，1989，8：8
102. J. Haginaka, J. Wakai. Anal. Chem, 1990, 62:997
103. A. M. Stalcup, H. L. Jin, D. W. Armstrong. J Chromatogr, 1990, 499:627
104. G. Vigh, G. Quintero, G. Farkas. J Chromatogr, 1990, 506:481
105．黄天宝，旷昌渝，周竞先，苟大明．色谱．1991，19：687
106. J. Florance, Z. Konteatis. J Chromatogr, 1991,543:299
107. S. Li, W.C. Purdy. J Chromatogr, 1991, 543:105
108. D. W. Armstrong, X. P. Yang, S. M. Han, R. A. Menges. Anal Chem, 1987, 59:2594
109. A. M. Stalcup, H. L. Jin, D. W. Armstrong. J. Liq. Chromatogr, 1990, 13:473
110. M.Tanaka, T. Shono, D. Zhu. J. Chromatogr, 1984, 301: 429
111. K. Fujimura, M. Kitagawa, H. Takayanagi, T. Anclo. J. Liq. Chromatogr, 1986, 9:607
112. D. W. Armstrong, A. M. Stalcug, M. L. Hilton, J. D. Dunlan, J. R. Faulkner. J Chromatogr, 1990, 62:1610
113. D. W. Armstrong, C-D. Chang, S.H. Lee. J Chromatogr, 1991, 539:83
114. A. M. Stalcup, C-D. Chang, D. W. Armstrong. J Chromatogr, 1991, 540:113
115. M. G. Cikalo, K. D. Bartle, M. M. Robson. Analyst, 1998, 123(7): 87R
116. F. Lelieve, C.Yan, R. N. Zare, B. Gaveil. J Chromatogr, 1996, 723:145
117. D. W. Armstrong, W. Demond. J Chromatogr. Sci, 1984, 22:411
118. W. Wei, G.A. Luo, R. Xiang. J Microcol Sep, 1999, 11(4): 263
119. D. W. Armstrong, Y. Tang, T. Ward. Anal chem, 1993, 65:1114
120. S. Li, D. K. Lloyd. J Chromatogr, 1994, 666:321
121. D. Wistuba, H. Czesla, M. Roeder, V. Schurig. J Chromatogr, 1994, 38:381
122．阮宗琴，尤进茂，李菊白，欧庆瑜．色谱，2000，18(2)：183
123. X. Y. Shi, Y. Q. Zhang, J. H. Han, R. N. Fu. J Chromatogr, 2000, 52:200
124. a) I. Sugiura, M. Komiyama, N. Toshima, H. Hirai. Bull. Chem. Soc. Jpn, 1989, 62(5): 1643 b) M. Komiyama, H. Hirai. Polym. 1987, 19:773 c) M. Komiyama, I. Sugiura, H. Hirai. J Coord. Chem., 1988, 18:181
125. E. Gil-Av, B. Febush, Bosita Charles-Sigler. Tetrahedron Lett, 1966:1009
126. E. Gil-Av, B. Febush. Tetrahedron Lett, 1967:3345
127. J. L. Ge. J Microcol. Sep, 1991, 3:211
128. H. Frank, G. J. Nicholson, E. Bayer. J. Chromatogr, 1977, 15:174
129. H. Frank, G. J. Nicholson, E. Bayer. Angew. Chem., 1978, 90:396
130. Dai Rongji, Zhang Shu, Li Fang. Acta Chim Sin, 1998, 56:594
131．冯钰锜，谢敏杰，达式禄．色谱，1999，20(11)：1708
132．冯钰锜，达式禄．色谱，2000，18(3)：224
133. I. Bako, L. Jicsinzky. J Jic. Phenom, 1994, 18:275
134. W. Zhou, R. Fu, R. Dai, Z. Huang, Y. Chen. HRC, 1994, 17:719
135. S. Li, W.C. Purdy. Anal. Chem, 1992, 64:1405
136. O. Guo, T. Ren, Y. Fang, Y. Liu. J Jic. Phenom, 1995, 22:251
137. B. Hosangadi, A. Asgaonkar. J. Jic. Phenom, 1995, 23:35
138. A. Berthod, W.Y. Li, D.W. Armstrong, Anal. Chem, 1992, 64:873
139. W. Dougherty, F. Liotta, D. Mondimore, W. Shum. Tetrahedron Lett, 1990, 30:4389
140. C. Bicchi, G.Artuffo, A. D'Amato, P. Evens. HRC, 1991, 14:701
141. A. Zhang, Z. J. Gong, J. Deng, H. Liu. J Chromatogr, 1990, 521:128
142. K. Kano, T. Ishimura, S. Negi. J. Jic. Phenom, 1995,22:285
143．顾峻岭，傅若农，分析化学，2001，9：1098
144．戴荣继．特殊选择性气相色谱手性固定相的合成及性能研究：[博士论文]．北京：北京理工大学化工与材料学院，1994