Skip to main content

Design and Construction of Supramolecular Architectures Consisting of Cyclodextrins and Polymers

  • Chapter
  • First Online:
Book cover Metal Complex Catalysts Supercritical Fluid Polymerization Supramolecular Architecture

Part of the book series: Advances in Polymer Science ((POLYMER,volume 133))

Abstract

Cyclodextrins (CDs) interact with various polymers of high specificity to give crystalline inclusion complexes in which CD molecules are threaded by a polymer chain. For example, α-CD forms such complexes with poly(ethylene glycol) (PEG) when the PEG molecular weight is higher than 200, but β-CD does not. On the other hand, for poly(propylene glycol) (PPG), the reverse is the case. Although both α and β-CD fail, γ-CD complexes with poly(methyl vinyl ether) (PMVE). In addition, α and γ-CD complex with oligo(ethylene) (OE) and poly(isobutylene) (PIB), respectively. Three quarters of the present paper describe the synthesis, structure, and properties of these CD-polymer inclusion complexes. The remaining part is concerned with rotaxanes including polyrotaxanes and also catenanes. A particularly detailed description is made concerning the work of the author and his coworkers which led to the synthesis of polyrotaxanes consisting of α-CD and PEG and the making of molecular tubes from them. It is expected that such tubes may find many useful applications in chemistry and biology.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Harada A (1994) Stereochemistry of Organometallic and Inorganic Compounds, Vol 5, Chains, Clusters, Inclusion Compounds, Paramagnetic Labels, and Organic Rings. Zanello P (ed), Elsevier, Amsterdam, p 409

    Google Scholar 

  2. Pedersen CJ (1967) J Am Chem Soc 89: 2495

    Article  CAS  Google Scholar 

  3. Lehn J-M (1988) Angew Chem Int Ed Engl 27: 89

    Article  Google Scholar 

  4. Cram DJ (1992) Nature 356: 29

    Article  CAS  Google Scholar 

  5. Shinkai S (1993) Tetrahedron 49: 8933

    Article  CAS  Google Scholar 

  6. Harada A (1994) Yukagaku 43: 839

    CAS  Google Scholar 

  7. Bender ML, Komiyama M (1978) Cyclodextrin chemistry. Springer-Verlag, Berlin

    Google Scholar 

  8. Szejtli J (1982) Cyclodextrins and Their Inclusion Complexes, Akademiai Kiado, Budapest

    Google Scholar 

  9. Saenger W (1976) Jerusalem Symp Quantum Chem Biochem (ed) Pullman EB, Reidel Co., Dordrecht

    Google Scholar 

  10. Harada A, Takahashi S (1984) J Chem Soc, Chem Commun 645

    Google Scholar 

  11. Harada A, Takahashi S (1984) J Inclusion Phenom 2: 791

    Article  CAS  Google Scholar 

  12. Harada A, Hu Y, Yamamoto S, Takahashi S (1988) J Chem Soc, Dalton Trans 729

    Google Scholar 

  13. Odagaki Y, Hirotsu K, Higuchi T, Harada A, Takahashi S (1990) J Chem Soc, Perkin Trans 1230

    Google Scholar 

  14. Shimada M, Harada A, Takahashi S (1991) J Chem Soc, Chem Commun 263

    Google Scholar 

  15. Harada A, Saeki K, Takahashi S (1987) J Inclusion Phenom 5: 601

    Article  CAS  Google Scholar 

  16. Harada A, Saeki K, Takahashi S (1988) Carbohydr. Res 192: 1

    Article  Google Scholar 

  17. Harada A, Takahashi S (1984) Chem Lett 2089

    Google Scholar 

  18. Harada A, Saeki K, Takahashi S (1985) Chem Lett 1157

    Google Scholar 

  19. Harada A, Takahashi S (1989) Organometallics 8: 730

    Article  CAS  Google Scholar 

  20. Harada A, Takeuchi M, Takahashi S (1986) Chem Lett 1893

    Google Scholar 

  21. Harada A, Takeuchi M, Takahashi S (1986) Bull Chem Soc Jpn 61: 4367

    Article  Google Scholar 

  22. Harada A, Takahashi S (1986) J Chem Soc, Chem Commun 1229

    Google Scholar 

  23. Harada A, Yamamoto S, Takahashi S (1989) Organometallics 8: 2560

    Article  CAS  Google Scholar 

  24. Harada A, Takahashi S (1989) J Macromol Sci, Chem A26: 373

    CAS  Google Scholar 

  25. Harada A, Hu Y, Takahashi S (1986) Chem Lett 2083

    Google Scholar 

  26. Hu Y, Uno M, Harada A, Takahashi S (1990) Chem Lett 797

    Google Scholar 

  27. Hu Y, Uno M, Harada A, Takahashi S (1991) Bull Chem Soc Jpn 64: 1884

    Article  CAS  Google Scholar 

  28. Hu Y, Harada A, Takahashi S (1990) J Mol Cat 60: L13

    Article  CAS  Google Scholar 

  29. Hu Y, Harada A, Takahashi S (1990) Synt Commun 8: 1607

    Google Scholar 

  30. Harada A, Takahashi S (1988) J Chem Soc, Chem Commun 1352

    Google Scholar 

  31. Harada A, Shimada M, Takahashi S (1989) Chem Lett 275

    Google Scholar 

  32. Klingert B, Rihs (1990) Organometallics 9: 1135

    Article  CAS  Google Scholar 

  33. Alston DR, Slawin AMZ, Stoddart JF, Williams DJ (1985) Angew Chem Int Ed Engl 24: 786

    Article  Google Scholar 

  34. Harada A, Furue M, Nozakura S (1976) Macromolecules 9: 701

    Article  CAS  Google Scholar 

  35. Harada A, Furue M, Nozakura S (1976) Macromolecules 9: 705

    Article  CAS  Google Scholar 

  36. Harada A, Furue M, Nozakura S (1977) Macromolecules 10: 676

    Article  CAS  Google Scholar 

  37. Harada A, Furue M, Nozakura S (1979) J Polym Sci. Polym Chem Ed 16: 189

    Article  Google Scholar 

  38. Harada A, Furue M, Nozakura S (1980) Polym J 12: 29

    Article  CAS  Google Scholar 

  39. Harada A, Furue M, Nozakura S (1980) Polym J 13: 777

    Article  Google Scholar 

  40. Ogata N, Sanui K, Wada J (1979) J Polym Sci Polym Lett 14: 459

    Google Scholar 

  41. Maciejewski MM (1979) J Macromol Sci, Chem A13, 77: 1175

    Article  Google Scholar 

  42. Kitano H, Okubo T (1977) J Chem Soc, Perkin II 432

    Google Scholar 

  43. Iijima T, Uemura T, Tsuzuku S, Komiyama J (1978) J Polym Sci, Polym Phys Ed 16: 793

    Article  CAS  Google Scholar 

  44. Harada A (1993) Polym. News 18: 358

    CAS  Google Scholar 

  45. Harada A, Kamachi M (1990) Macromolecules 23: 2821

    Article  CAS  Google Scholar 

  46. Harada A, Li J, Kamachi M (1993) Proc Jpn Acad 69: Ser. B 39

    Google Scholar 

  47. Harada A, Li J, Kamachi M (1993) Macromolecules 26: 5698

    Article  CAS  Google Scholar 

  48. Harada A, Li J, Kamachi M (1992) Nature 356: 325

    Article  CAS  Google Scholar 

  49. Harada A, Li J, Kamachi M (1993) Carbohydr Carbohydr Polym 25: 266

    Google Scholar 

  50. Harada A, Nakamitsu T, Li J, Kamachi M (1993) J Org Chem 58: 7524

    Article  CAS  Google Scholar 

  51. Harada A (1996) Coord Chem Rev in press

    Google Scholar 

  52. Harada A (1995) Pharmacia 31: 1263

    CAS  Google Scholar 

  53. Harada A, Kamachi M (1994) J Chem Soc Jpn, Chem & Ind Chem 1994, 587

    Google Scholar 

  54. Harada A (1994) Seisan to Gijutu 46: 62

    Google Scholar 

  55. Harada A (1994) Yukagaku 43: 839

    CAS  Google Scholar 

  56. Harada A (1995) Biohistory 3: 25

    Google Scholar 

  57. Harada A, Kamachi M (1992) Hyomen/Surface 30: 110

    CAS  Google Scholar 

  58. Harada A (1994) Hyomen/Surface 32: 125

    CAS  Google Scholar 

  59. Harada A, Li J, Kamachi M (1994) Macromolecules 27: 4538

    Article  CAS  Google Scholar 

  60. Bomer B, Heitz W, Kern W (1970) J Chromatogr 53: 51

    Article  Google Scholar 

  61. Harada A, Li J, Kamachi M (1994) Nature 370: 126

    Article  CAS  Google Scholar 

  62. Li J, Harada A, Kamachi M (1994) Polym J 26: 1019

    Article  CAS  Google Scholar 

  63. Harada A, Kamachi M (1990) J Chem Soc Chem Commun 1322

    Google Scholar 

  64. Harada A, Okada M, Li J, Kamachi M (1995) Macromolecules 28: 8406

    Article  CAS  Google Scholar 

  65. Harada A, Li J, Kamachi M (1993) Chem Lett 237

    Google Scholar 

  66. Harada A, Okada M, Kamachi M (1996) Acta Polymerica, in press

    Google Scholar 

  67. Harada A, Okada M, Kamachi M (1995) Proc Bilat Symp Polym Mater Sci (1995) 180

    Google Scholar 

  68. Harada A, Suzuki S, Nakamitsu T, Okada M, Kamachi M (1995) Kobunshi Ronbunshu, 52: 594

    CAS  Google Scholar 

  69. Steiner T, Koellner G, Saenger W (1992) Carbohydr Res (1992) 228: 321

    Article  CAS  Google Scholar 

  70. Harada A, Kamachi M (1994) J Synth Org Chem Jpn 52: 831

    CAS  Google Scholar 

  71. Li J, Harada A, Kamachi M (1994) Bull Chem Soc Jpn 67: 2808

    Article  CAS  Google Scholar 

  72. Yonemura H, Saito H, Matsushima S, Nakamura H, Matsuo T (1989) Tetrahedron Lett 30: 3143

    Article  CAS  Google Scholar 

  73. Saito H, Yonemura H, Nakamura H, Matsuo T (1990) Chem Lett 535

    Google Scholar 

  74. Watanabe M, Nakamura H, Matsuo T (1992) Bull Chem Soc Jpn 65: 164

    Article  CAS  Google Scholar 

  75. Harada A, Suzuki S, Li J, Kamachi M (1993) Macromolecules 26: 5267

    Article  CAS  Google Scholar 

  76. Lehn J-M (1992) Angew Chem Int Ed Engl 29: 1304

    Article  Google Scholar 

  77. Schill G (1971) Catenanes Rotaxanes and Knots, Academic Press, New York

    Google Scholar 

  78. Agam G, Graiver D, Zilkha A (1976) J Am Chem Soc 98: 5206

    Article  CAS  Google Scholar 

  79. Harrison IT, Harrison S (1967) J Am Chem Soc 89: 5723

    Article  CAS  Google Scholar 

  80. Harrison IT (1972) J Chem Soc Chem Commun 231

    Google Scholar 

  81. Annelli PL, Ashton PR, Ballardini R, Balazani V, Delgado M, Gandolfi MT, Goodnow TT, Kaifer AE, Philp D, Pietraszkiewicz M, Prodi L, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1992) J Am Chem Soc 114: 193

    Article  Google Scholar 

  82. Allwood BL, Spencer N, Zavareh HS, Stoddart JF, Williams DJ (1987) J Chem Soc Chem Commun 1064

    Google Scholar 

  83. Ashton PR, Philp D, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1991) J Chem Soc Chem Commun 1680

    Google Scholar 

  84. Ashton PR, Belohradsky M, Philp D, Stoddart JF (1993) J Chem Soc Chem Commun 1269

    Google Scholar 

  85. Ashton PR, Belohradsky M, Philp D, Stoddart JF (1993) J Chem Soc Chem Commun 1274

    Google Scholar 

  86. Odel B, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1988) Angew Chem Int Ed Engl 27: 1547

    Article  Google Scholar 

  87. Ashton PR, Odell B, Reddington MV, Slawin AMZ, Stoddart JF, Williams DJ (1988) Angew Chem Int Ed Engl 27: 1550

    Article  Google Scholar 

  88. Reddingon MV, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1991) J Chem Soc Chem Commun 630

    Google Scholar 

  89. Anelli PL, Ashton PR, Spencer N, Slawin AMZ, Stoddart JF, Williams DJ (1991) Angew Chem Int Ed Engl 30: 1036

    Article  Google Scholar 

  90. Ashton PR, Philp D, Spencer N, Stoddart JF (1991) J Chem Soc Chem Commun 1677

    Google Scholar 

  91. Ashton PR, Johnston MR, Stoddart JF, Tolley MS, Wheeler JW (1992) J Chem Soc Chem Commun 1128

    Google Scholar 

  92. Chambron J-C, Heitz V, Sauvage J-P (1992) J Chem Soc Chem Commun 1131

    Google Scholar 

  93. Anelli L, Spencer N, Stoddart JF (1991) J Am Chem Soc 113: 5131

    Article  CAS  Google Scholar 

  94. Ashton PR, Philp D, Spencer N, Stoddart JF (1992) J Chem Soc Chem Commun 1124

    Google Scholar 

  95. Ballardini R, Balzani, Gandolfi VMT, Prodi L, Venturi M, Philp D, Ricketts HG, Stoddart JF (1993) Angew Chem Int Ed Engl 32: 1301

    Article  Google Scholar 

  96. Benniston AC, Harriman A (1993) Angew Chem Int Ed Engl 32: 1459

    Article  Google Scholar 

  97. Bissell RA, Cordova E, Kaifer AE, Stoddart JF (1994) Nature 369: 133

    Article  CAS  Google Scholar 

  98. Stoddart JF (1992) Angew Chem Int Ed Engl 31: 846

    Article  Google Scholar 

  99. Ogino H (1981) J Am Chem Soc 103: 1303

    Article  CAS  Google Scholar 

  100. Ogino H, Ohata K (1984) Inorg Chem 23: 3312

    Article  CAS  Google Scholar 

  101. Manka JS, Lawrence DS (1990) J Am Chem Soc 112: 2440

    Article  CAS  Google Scholar 

  102. Rao TVS, Lawrence DS (1990) J Am Chem Soc 112: 3614

    Article  CAS  Google Scholar 

  103. Dick DL, Rao TVS, Sukumaran D, Lawrence DS (1992) J Am Chem Soc 114: 2664

    Article  CAS  Google Scholar 

  104. Isnin R, Kaifer AE (1991) J Am Chem Soc 113: 8188

    Article  CAS  Google Scholar 

  105. Wylie RS, Macartney DH (1992) J Am Chem Soc 114: 3136

    Article  CAS  Google Scholar 

  106. Wenz G, Bey E, Schmidt L (1992) Angew Chem Int Ed 31: 783

    Article  Google Scholar 

  107. Kunitake M, Kotoo K, Manabe O, Muramatsu T, Nakashima N (1993) Chem Lett 1033

    Google Scholar 

  108. Harada A, Li J, Kamachi M, Polymer Preprint, in press

    Google Scholar 

  109. Gibson HW, Marand H (1993) Adv Mater 5: 11

    Article  CAS  Google Scholar 

  110. Sjen YX, Xie D, Gibson HW (1994) J Am Chem Soc 116: 537

    Article  Google Scholar 

  111. Frisch HL, Wasserman E (1961) J Am Chem Soc 83: 3789

    Article  CAS  Google Scholar 

  112. Ashton PR, Goodnow TT, Kaifer AE, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vicdent C, Williams DJ (1989) Angew Chem Int Ed Engl 28: 1396

    Article  Google Scholar 

  113. Amabilino DB, Ashton PR, Tolley MS, Stoddart JF, Williams DJ (1993) Angew Chem Int Ed Engl 32: 1297

    Article  Google Scholar 

  114. Ashton PR, Philp D, Spencer N, Stoddart JF, Williams DJ (1994) J Chem Soc Chem Commun 181

    Google Scholar 

  115. Ashton PR, Brown CL, Chrystal EJT, Goodnow TT, Kaifer AE, Parry KP, Philp D, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1991) J Chem Soc Chem Commun 634

    Google Scholar 

  116. Ashton PR, Brown CL, Chrystal EJT, Goodnow TT, Kaifer AE, Parry KP, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1991) Angew Chem Int Ed Engl 30: 1039

    Article  Google Scholar 

  117. Amabilino DB, Ashton PR, Reder AS, Spencer N, Stoddart JF (1994) Angew Chem Int Ed Engl 33: 433

    Article  Google Scholar 

  118. Amabilino DB, Ashton PR, Reder AS, Spencer N, Stoddart JF (1994) Angew Chem Int Ed Engl 33: 1286

    Article  Google Scholar 

  119. Pietraszkiewicz, Spencer N, and Stoddart JF (1991) Angew Chem Int Ed Engl 30: 1042

    Article  Google Scholar 

  120. Buchecker COD, Sauvage J-P (1987) Chem Rev 87: 795

    Article  Google Scholar 

  121. Chambron JC, Heitz V, Sauvage J-P (1993) J Am Chem Soc 115: 12378

    Article  CAS  Google Scholar 

  122. Buchecker COD, Guilhem J, Pascard C, Sauvage J-P (1990) Angew Chem Int Ed Engl 29:1154

    Article  Google Scholar 

  123. Bitsch F, Buchecker COD, Khemiss A-K, Sauvage J-P, Dorsselaer AV (1991) J Am Chem Soc 113:4023

    Article  CAS  Google Scholar 

  124. Fujita M, Ibukuro F, Hagihara H, Ogura K (1994) Nature 367: 720

    Article  CAS  Google Scholar 

  125. Luttringhous, Cramer F, Prinzbach H, Henglein FM (1958) Liebigs An Chem 613: 185

    Article  Google Scholar 

  126. Armspach D, Ashton PR, Moore CP, Spencer N, Stoddart JF, Wear TJ, Williams DJ (1993) Angew Chem Int Ed Engl 32: 854

    Article  Google Scholar 

  127. Harada A, Li J, Kamachi M, unpublished.

    Google Scholar 

  128. Vogtle F, Meier S, Hoss R (1992) Angew Chem Int Ed Engl 31: 1619

    Article  Google Scholar 

  129. Vogtle F, Muller WM, Muller U, Bauer M, Rissanen K (1993) Angew Chem Int Ed Engl 32: 1295

    Article  Google Scholar 

  130. Gunter MJ, Johnston MR (1992) J Chem Soc Chem Commun 1163

    Google Scholar 

  131. Harada A, Kamachi M (1994) Ordering in Macromolecular Systems, Springer-Verlag, Berlin, 69

    Google Scholar 

  132. Wenz G, Keller B (1992) Angew Chem Int Ed Engl 31: 197

    Article  Google Scholar 

  133. Harada A, Li J, Kamachi M (1993) J Am Chem Soc 116: 3192

    Article  Google Scholar 

  134. Harada A, Li J, Kamachi M (1993) Nature 364: 516

    Article  CAS  Google Scholar 

  135. Harada A, Li J, Kamachi M (1995) Macromolecular Engineering, Ed, Mishra MK, Nuyken O, Kobayashi S, Yagci Y, and Sar B, p 127, Plenum Press, New York

    Google Scholar 

  136. Harada A, Li J, Kamachi M (1995) J Macromol Sci, Macromol Rep A32: 813

    CAS  Google Scholar 

  137. Harada A (1995) KOBUNSHI/High Polymers Japan 44: 390

    CAS  Google Scholar 

  138. Harada A, Kamachi M (1992) KOBUNSHI/High Polymers Japan 41: 814

    CAS  Google Scholar 

  139. Harada A, Kamachi M (1992) Kagaku/Chemistry 47: 634

    CAS  Google Scholar 

  140. Harada A (1992) Kagaku/Chemistry 47: 631

    Google Scholar 

  141. Harada A, Kamachi M (1995) Chem & Chem Ind Jpn 48: 899

    CAS  Google Scholar 

  142. Harada A, Kamachi M (1996) Supramolecular Science, in press

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

D. A. Canelas J. M. DeSimone A. Harada E. Ihara K. Mashima A. Nakamura Y. Nakayama H. Yasuda

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Harada, A. (1997). Design and Construction of Supramolecular Architectures Consisting of Cyclodextrins and Polymers. In: Canelas, D.A., et al. Metal Complex Catalysts Supercritical Fluid Polymerization Supramolecular Architecture. Advances in Polymer Science, vol 133. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68442-5_4

Download citation

  • DOI: https://doi.org/10.1007/3-540-68442-5_4

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-62699-2

  • Online ISBN: 978-3-540-68442-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics