Skip to main content
SpringerLink
Log in

Heteroaromatic Modules for Self-Assembly Using Multiple Hydrogen Bonds

  • Chapter
  • First Online:
Molecular Self-Assembly Organic Versus Inorganic Approaches

Part of the book series: Structure and Bonding ((STRUCTURE,volume 96))

Abstract

Hydrogen bonding is a directional and moderately strong intermolecular force. Compounds that present multiple hydrogen-bond donor and acceptor groups have proven to be extremely important in creating new self-assembled structures. A review of several classes of organic compounds capable of multiple hydrogen-bond recognition is presented with a focus on the factors that contribute to complex stability.

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

Access this chapter

Log in via an institution
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. Breslow R (1998) Chem Biol 5: R27

    Article  CAS  Google Scholar 

  2. Breslow R (1995) Acc Chem Res 28: 146

    Article  CAS  Google Scholar 

  3. Eigen M, De Maeyer L (1966) Naturwissenschaften 53: 50

    Article  CAS  Google Scholar 

  4. Lehn JM (1988) Angew Chem 27: 89

    Article  Google Scholar 

  5. Zimmerman SC, Murray TJ (1994) In: Wipff G (ed) Computational approaches in supramolecular chemistry. NATO ASI Series, vol 426. Kluwer, Amsterdam, p 109

    Google Scholar 

  6. Kyogoku Y, Lord RC, Rich A (1967) Proc Natl Acad Sci USA 57: 250

    Article  CAS  Google Scholar 

  7. Bell TW, Hou Z, Zimmerman SC, Thiessen PA (1995) Angew Chem Int Ed Engl 34: 2163 and references cited therein

    Article  CAS  Google Scholar 

  8. Hamilton AD, Pant N, Muehldorf A (1988) Pure Appl Chem 60: 533

    Article  CAS  Google Scholar 

  9. Rebek J Jr (1990) Angew Chem Int Ed Engl 29: 245

    Article  Google Scholar 

  10. Zimmerman SC, Wu W (1989) J Am Chem Soc 111: 8054

    Article  CAS  Google Scholar 

  11. Kelly TR, Maguire MP (1987) J Am Chem Soc 109: 6549

    Article  CAS  Google Scholar 

  12. Kirnos MD, Khudyakov IY, Alexandrushikina NI, Vanyushin BF (1997) Nature 270: 369

    Article  Google Scholar 

  13. Gryaznov S, Schultz RG (1994) Tetrahedron Lett 35: 2489 and references cited therein

    Article  CAS  Google Scholar 

  14. Haaima G, Hansen HF, Christensen L, Dahl O, Nielsen PE (1997) Nucleic Acids Res 25: 4639

    Article  CAS  Google Scholar 

  15. Hamilton AD, Van Engen D (1987) J Am Chem Soc 109: 5035

    Article  CAS  Google Scholar 

  16. Park TK, Schroeder J, Rebek J Jr (1991) J Am Chem Soc 113: 5125

    Article  CAS  Google Scholar 

  17. Schneider HJ, Juneva RK, Simova S (1989) Chem Ber 122: 1211

    Article  CAS  Google Scholar 

  18. Kelly TR, Bridger GJ, Zhao C (1990) J Am Chem Soc 112: 8024

    Article  CAS  Google Scholar 

  19. Murray TJ, Zimmerman SC (1992) J Am Chem Soc 114: 4010

    Article  CAS  Google Scholar 

  20. Beijer FH, Sijbesma RP, Vekemans JAJM, Meijer EW, Kooijman H, Spek AL (1996) J Org Chem 61: 6371

    Article  CAS  Google Scholar 

  21. Adrian JC Jr, Wilcox CS (1991) J Am Chem Soc 113: 678

    Article  CAS  Google Scholar 

  22. Murray TJ, Zimmerman SC, Kolotuchin SV (1994) Tetrahedron 51: 635 and references cited therein

    Article  Google Scholar 

  23. Feibush B, Figueroa A, Rosita C, Onan KD, Feibush P, Karger BL (1986) J Am Chem Soc 108: 3310

    Article  CAS  Google Scholar 

  24. Hamilton AD, Van Engen D (1987) J Am Chem Soc 109: 5035

    Article  CAS  Google Scholar 

  25. Leonard NJ, McCredie RS, Logue MW, Cunddall RL (1973) J Am Chem Soc 95: 2320

    Article  CAS  Google Scholar 

  26. Sessler JL, Wang R (1998) J Org Chem 63: 4079

    Article  CAS  Google Scholar 

  27. Hamilton AD, Little D (1990) J Chem Soc Chem Commun 297

    Google Scholar 

  28. Schall OF, Gokel GW (1994) J Am Chem Soc 116: 6089

    Article  CAS  Google Scholar 

  29. Kotera M, Lehn J-M, Vigneron JP (1995) Tetrahedron 51: 1953

    Article  CAS  Google Scholar 

  30. Prins LJ, Huskens J, de Jong F, Timmerman P, Reinhoudt DN (1999) Nature 398: 498

    Article  CAS  Google Scholar 

  31. Mammen M, Simanek EE, Whitesides GM (1996) J Am Chem Soc 118: 12614

    Article  CAS  Google Scholar 

  32. Berstein J, Sterns B, Shaw E, Lott WA (1947) J Am Chem Soc 69: 1151

    Article  Google Scholar 

  33. Berman A, Izraeli ES, Levanon H, Wang B, Sessler JL (1995) J Am Chem Soc 117: 8252

    Article  CAS  Google Scholar 

  34. Sessler JL, Wang B, Harriman A (1993) J Am Chem Soc 115: 10418

    Article  CAS  Google Scholar 

  35. Roberts C, Bandaru R, Switzer C (1997) J Am Chem Soc 119: 4640

    Article  CAS  Google Scholar 

  36. Kral V, Sessler JL (1995) Tetrahedron 51: 539

    Article  CAS  Google Scholar 

  37. Hisatome M, Ikeda K, Kishibata S, Yamakawa K (1993) Chem Lett 1357

    Google Scholar 

  38. Chen L, Sakai N, Moshiri ST, Matile S (1998) Tetrahedron Lett 39: 3627

    Article  CAS  Google Scholar 

  39. Fenlon EE, Murray TJ, Baloga MH, Zimmerman SC (1993) J Org Chem 58: 6625

    Article  CAS  Google Scholar 

  40. Marsh A, Nolen EG, Gardinier KM, Lehn J-M (1994) Tetrahedron Lett 35: 397

    Article  CAS  Google Scholar 

  41. Marsh A, Silvestri M, Lehn J-M (1996) Chem Commun 1527

    Google Scholar 

  42. Lehn J-M, Mascal M, DeCian A, Fischer J (1992) J Chem Soc Perkin Trans 2: 461

    Google Scholar 

  43. Petersen P, Wu W, Fenlon EE, Kim S, Zimmerman SC (1996) Bioorg Med Chem 4: 1107

    Article  CAS  Google Scholar 

  44. Kolotuchin SV, Zimmerman SC (1998) J Am Chem Soc 120: 9092

    Article  CAS  Google Scholar 

  45. Mascal M, Hext NM, Warmuth R, Moore MH, Turkenburg JP (1996) Angew Chem Int Ed Engl 35: 2204

    Article  CAS  Google Scholar 

  46. Meyer H, Bossert F, Horstmann H (1978) Liebigs Ann Chem 1476

    Google Scholar 

  47. Bell DA, Anslyn EV (1995) Tetrahedron 51: 7161

    Article  CAS  Google Scholar 

  48. Beijer FH, Kooijman H, Spek AL, Sijbesma RP, Meijer EW (1998) Angew Chem Int Ed Engl 37: 75

    Article  CAS  Google Scholar 

  49. Corbin PS, Zimmerman SC (1998) J Am Chem Soc 120: 9710

    Article  CAS  Google Scholar 

  50. Beijer FH, Sijbesma RP, Kooijman H, Spek AL, Meijer EW (1998) J Am Chem Soc 120: 6761

    Article  CAS  Google Scholar 

  51. Sijbesma RP, Beijer FH, Brunsveld L, Folmer BJB, Hirschberg JHK, Lange RFM, Lowe JKL, Meijer EW (1997) Science 278: 1601

    Article  CAS  Google Scholar 

  52. Pfleiderer M, Pfleiderer W (1992) Heterocycles 33: 905

    Article  CAS  Google Scholar 

  53. Corbin PS, unpublished results

    Google Scholar 

  54. Sessler JL, Wang R (1998) Angew Chem Int Ed Engl 37: 1726

    Article  CAS  Google Scholar 

  55. Liming U, Kühl C (1998) Tetrahedron Lett 39: 5735

    Article  Google Scholar 

  56. Corbin P, Zimmerman SC, submitted for publication

    Google Scholar 

  57. Jorgensen WL (1998) J Phys Chem 102: 3782

    Google Scholar 

  58. Hopkins HP, Alexander CJ, Ali SZ (1978) J Phys Chem 82: 1268

    Article  CAS  Google Scholar 

  59. Schneider HJ, Juneva RK, Simova S (1989) Chem Ber 122: 1211. This analysis has been updated to include secondary hydrogen bonding (see [61])

    Article  CAS  Google Scholar 

  60. Jorgensen WL, Pranata J (1990) J Am Chem Soc 112: 2008; Pranata J, Wierschke SG, Jorgensen WL (1991) J Am Chem Soc 113: 2810

    Article  CAS  Google Scholar 

  61. Zimmerman SC, Murray TJ (1994) Tetrahedron Lett 35: 4077

    Article  CAS  Google Scholar 

  62. Gardner RR, Gellman SH (1995) J Am Chem Soc 117: 10411

    Article  CAS  Google Scholar 

  63. Sartorius J, Schneider HJ (1996) Eur J Chem 2: 1446

    Article  CAS  Google Scholar 

  64. Cram DJ (1986) Angew Chem Int Ed Engl 25: 1039

    Article  Google Scholar 

  65. Cram DJ, Trueblood KN (1985) in Vogtle F, Weber E (eds) Host guest complex chemistry, macrocycles. Springer, Berlin Heidelberg New York, p 125

    Google Scholar 

  66. Zimmerman SC, Mrksich M, Baloga M (1989) J Am Chem Soc 111: 8528

    Article  CAS  Google Scholar 

  67. Page MI, Jencks WP (1971) Proc Natl Acad Sci USA 68: 1678

    Article  CAS  Google Scholar 

  68. Searle MS, Williams DH (1992) J Am Chem Soc 114: 10690

    Article  CAS  Google Scholar 

  69. Eblinger F, Schneider HJ (1998) Angew Chem Int Ed Engl 37: 826. This paper, which claims to report the first study wherein the number of free rotations within supramolecular complexes are systematically varied (see however [64]), studies the interaction between dicarboxylates and diamide. It is complicated by the fact that rigid and flexible dicarboxylates may bind the diamides in different orientations

    Article  CAS  Google Scholar 

  70. Hamilton AD, Pant N (1998) J Chem Soc Chem Commun 765

    Google Scholar 

  71. Murray TJ, Zimmerman SC (1995) Tetrahedron Lett 36: 7627

    Article  CAS  Google Scholar 

  72. Watson JD, Crick FHC (1953) Nature 171: 964

    Article  CAS  Google Scholar 

  73. Douhal A, Kim SK, Zewail AH (1995) Nature 378: 260

    Article  CAS  Google Scholar 

  74. Robinson H, Gao YG, Bauer C, Roberts C, Switzer C, Wang AHJ (1998) Biochemistry 37: 10897

    Article  CAS  Google Scholar 

  75. Goodman MF (1995) Nature 378: 237

    Article  CAS  Google Scholar 

  76. Beak P (1977) Acc Chem Res 10: 186

    Article  CAS  Google Scholar 

  77. Fersht AR (1987) Trends Biochem Sci 12: 301

    Article  CAS  Google Scholar 

  78. Fan E, van Araman S, Kincaid S, Hamilton AD (1993) J Am Chem Soc 115: 369; Wilcox CS, Kim EI, Romano D, Kuo LH, Burt AR, Curran DP (1995) Tetrahedron 55: 621

    Article  CAS  Google Scholar 

  79. Hamilton AD, Fan E, Van Arman S, Vicent C, Tellado FG, Geib SJ (1993) Supramol Chem 1: 247

    Article  CAS  Google Scholar 

  80. Drain CM, Fischer R, Nolen EG, Lehn J-M (1993) J Chem Soc Chem Commun 243

    Google Scholar 

  81. Zerkowski JA, Seto CT, Whitesides GM (1992) J Am Chem Soc 114: 5473

    Article  CAS  Google Scholar 

  82. Seto CT, Whitesides GM (1993) J Am Chem Soc 115: 905

    Article  CAS  Google Scholar 

  83. Crego Calama M, Fokken R, Nibbering NMM, Timmerman P, Reinhoudt DN (1998) J Chem Soc Chem Commun 1021

    Google Scholar 

  84. Kimizuka N, Kawasaki T, Hirata K, Kunitake T (1995) J Am Chem Soc 117: 6360

    Article  CAS  Google Scholar 

  85. Lehn J-M, Mascal M, DeCian A, Fischer J (1990) J Chem Soc Chem Commun 479

    Google Scholar 

  86. Ariga K, Kunitake T (1998) Acc Chem Res 31: 371 and references cited therein

    Article  CAS  Google Scholar 

  87. Bohanon TM, Denzinger S, Fink R, Paulus W, Ringsdorf H, Weck M (1995) Angew Chem 34: 58

    Article  CAS  Google Scholar 

  88. Nowick JS, Cao T, Noronha G (1994) J Am Chem Soc 116: 3285

    Article  CAS  Google Scholar 

  89. Zimmerman N, Moore JS, Zimmerman SC (1998) Chem Ind 604

    Google Scholar 

  90. Gulick-Krymicki T, Fouquey AM, Lehn J-M (1993) Proc Natl Acad Sci 90: 163

    Article  Google Scholar 

  91. Kotera M, Lehn J-M, Vigneron JP (1994) J Chem Soc Chem Commun 197

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA

    Steven C. Zimmerman & Perry S. Corbin

Authors
  1. Steven C. Zimmerman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Perry S. Corbin
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Applied Chemistry Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, 464-8603, Japan

    Makoto Fuiita

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Zimmerman, S.C., Corbin, P.S. (2000). Heteroaromatic Modules for Self-Assembly Using Multiple Hydrogen Bonds. In: Fuiita, M. (eds) Molecular Self-Assembly Organic Versus Inorganic Approaches. Structure and Bonding, vol 96. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46591-X_3

Download citation

  • DOI: https://doi.org/10.1007/3-540-46591-X_3

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-66948-7

  • Online ISBN: 978-3-540-46591-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation