Skip to main content
SpringerLink
Log in

Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs for Crystal Engineering

  • Chapter
  • First Online:
Design of Organic Solids

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 198))

Abstract

The design of new architectures for the purpose of crystal engineering has generated great interest in recent years. In particular, organic compounds have been the focus of many studies due to the presence of functional groups that can form strong and stable intermolecular interactions. Therefore, recognizing geometry and functionality at the molecular level has relevant implications in the design of supramolecular patterns. These patterns in turn can be translated to physical or chemical properties in a solid. This article is a presentation of compounds that have been designed for the purpose of molecular recognition and crystal engineering. In particular our focus will be directed towards organic structures based on the tape, ribbon, and sheet motifs. Several approaches in the design of functional solids will be presented, emphasizing the use of certain complementary intermolecular interactions for this purpose. It is not our attempt to define all concepts used for crystal engineering, but to present recent advances in this field.

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 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover 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. Schmidt GMJ (1971) Pure Appl Chem 27:647

    CAS  Google Scholar 

  2. Desiraju GR (1989) Crystal engineering, the design of organic solids. Elsevier, Amsterdam

    Google Scholar 

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

    Article  Google Scholar 

  4. Dunitz JD (1991) Pure Appl Chem 63:177

    Article  CAS  Google Scholar 

  5. Braga D, Grepioni F (1994) Acc Chem Res 27:51

    Article  CAS  Google Scholar 

  6. Hulliger J (1994) Angew Chem Int Ed Engl 33:143

    Article  Google Scholar 

  7. Vainshtein BK, Fridkin VM, Indenbom VL (1994) Structure of crystals, 2nd edn. Springer, Berlin

    Google Scholar 

  8. Desiraju GR (1995) The crystal as a supramolecular entity. Wiley, Chichester

    Google Scholar 

  9. Aakeröy CB, Seddon KR (1993) Chem Soc Rev 22:397

    Article  Google Scholar 

  10. Zaworotko MJ (1994) Chem Soc Rev 283

    Google Scholar 

  11. Maddox J (1988) Nature 335:201

    Article  Google Scholar 

  12. Wald G (1954) Sci Am 191:44

    Article  Google Scholar 

  13. Lawrence DS, Jiang T, Levett M (1995) Chem Rev 95:2229

    Article  CAS  Google Scholar 

  14. Fyfe MCT, Stoddart JF (1997) Acc Chem Res 30:393

    Article  CAS  Google Scholar 

  15. Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311

    Article  CAS  Google Scholar 

  16. Leiserowitz L (1976) Acta Crystallogr B32:775

    CAS  Google Scholar 

  17. Leiserowitz L, Schmidt GMJ (1969) J Chem Soc 2372

    Google Scholar 

  18. Garcia-Tellado F, Geib SJ, Goswami S, Hamilton AD (1991) J Am Chem Soc 113:9265

    Article  CAS  Google Scholar 

  19. Lady JH, Whetsel KB (1964) J Phys Chem 68:1001

    Article  CAS  Google Scholar 

  20. MacDonald JC, Whitesides GM (1994) Chem Rev 94:2383

    Article  CAS  Google Scholar 

  21. Panunto TW, Urbánczyk-Lipkowska Z, Johnson R, Etter MC (1987) J Am Chem Soc 109:7786

    Article  CAS  Google Scholar 

  22. Herbstein FH (1996) 1,3,5-Benzenetricarboxylic acid (trimesic acid) and some analogues. Lehn J-M, Atwood JL et al. (eds) In: Solid state supramolecular chemistry: crystal engineering. Pergamon, New York, chap 3. See also: Herbstein FH (1987) In: Weber E (ed) Molecular inclusion and molecular recognition-clathrates I. Topics in Current Chemistry, vol 140. Springer, Berlin Heidelberg New York, p 107

    Google Scholar 

  23. Etter MC, Frankenbach GM (1989) Chem Mater 1:10

    Article  CAS  Google Scholar 

  24. Zeegers-Huyskens T, Huyskens P (1991) Intermolecular forces-an introduction to modern methods and results. Springer-Verlag, Berlin Heidelberg New York

    Google Scholar 

  25. Atkins PW (1989) General chemistry. Scientific American Books, New York

    Google Scholar 

  26. Vinogradov SN, Linnell RH (1971) Hydrogen bonding. Van Nostrand Reinhold, New York

    Google Scholar 

  27. Etter MC (1990) Acc Chem Res 23:120

    Article  CAS  Google Scholar 

  28. Etter MC (1991) J Phys Chem 95:4601

    Article  CAS  Google Scholar 

  29. Jeffrey GA, Saenger W (1991) Hydrogen bonding in biological structures. Springer, Berlin

    Google Scholar 

  30. Jeffrey GA (1997) An introduction to hydrogen bonding. Oxford University Press, New York

    Google Scholar 

  31. Taylor R, Kennard O (1984) Acc Chem Res 17:320

    Article  CAS  Google Scholar 

  32. Philp D, Stoddart JF (1996) Angew Chem Int Ed Engl 35:1155

    Article  CAS  Google Scholar 

  33. Turi L, Dannenberg JJ (1993) J Phys Chem 97:7899

    Article  CAS  Google Scholar 

  34. Emsley J (1980) Chem SocRev 9:91

    CAS  Google Scholar 

  35. McMahon TB, Larson JW (1982) J Am Chem Soc 104:5848

    Article  Google Scholar 

  36. Taylor R, Kennard O (1983) Acta Crystallogr B39:133

    CAS  Google Scholar 

  37. Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555

    Article  CAS  Google Scholar 

  38. Frankenbach GM, Etter MC (1992) Chem Mater 4:272

    Article  CAS  Google Scholar 

  39. Bailey M, Brown CJ (1967) Acta Crystallogr 22:387

    Article  CAS  Google Scholar 

  40. Alcala R, Martinez-Carrera S (1972) Acta Crystallogr B28:1671

    Google Scholar 

  41. Duchamp DJ, March RE (1969) Acta Crystallogr B25:5

    Google Scholar 

  42. Ermer O (1988) J Am Chem Soc 110:3747

    Article  CAS  Google Scholar 

  43. Yang J, Marendaz J-L, Geib SJ, Hamilton AD (1994) Tetrahedron Lett 35:3665

    Article  CAS  Google Scholar 

  44. Yang J (1996) PhD thesis, University of Pittsburgh

    Google Scholar 

  45. Valiyaveettil S, Enkelmann V, Müllen K (1994) J Chem Soc Chem Commun 2097

    Google Scholar 

  46. Eichhorst-Gerner K, Stabel A, Moessner G, Declerq D, Valiyaveettil S, Enkelmann V, Müllen K, Rabe JP (1996) Angew Chem Int Ed Engl 35:1492

    Article  CAS  Google Scholar 

  47. Herbstein FH, Kapon M, Reisner GM (1987) J Inclusion Phenom 5:211

    Article  CAS  Google Scholar 

  48. Kolotuchin SV, Fenlon EE, Wilson SR, Loweth CJ, Zimmerman SC (1995) Angew Chem Int Ed Engl 34:2654

    Article  CAS  Google Scholar 

  49. Melendez RE, Sharma CVK, Zaworotko MJ, Bauer C, Rogers RD (1996) Angew Chem Int Ed Engl 35:2213

    Article  CAS  Google Scholar 

  50. Ducharme Y, Wuest JD (1988) J Org Chem 53:5787

    Article  CAS  Google Scholar 

  51. Etter MC, Adsmond DA (1990) J Chem Soc Chem Commun 589

    Google Scholar 

  52. Penfold BR, White JCB (1959) Acta Cryst 12:130

    Article  CAS  Google Scholar 

  53. Zhao X, Chang Y-L, Fowler FW, Lauher JW (1990) J Am Chem Soc 112:6627

    Article  CAS  Google Scholar 

  54. Gallant M, Viet MTP, Wuest JD (1991) J Org Chem 56:2284

    Article  CAS  Google Scholar 

  55. Brienne M-J, Gabard J, Leclercq M, Lehn J-M, Cesario M, Pascard C, Cheve M, Dutruc-Rosset G (1994) Tetrahedron Lett 35:8157

    Article  CAS  Google Scholar 

  56. Wang Y, Wei B, Wang Q (1990) J Crystallogr Spectrosc Res 20:79

    Article  CAS  Google Scholar 

  57. Zerowski JA, Seto CT, Wierda DA, Whitesides GM (1990) J Am Chem Soc 112:9025

    Article  Google Scholar 

  58. Zerkowski JA, MacDonald JC, Seto CT, Wierda DA, Whitesides GM (1994) J Am Chem Soc 116:2382

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  62. Scheinbeim J, Schempp E (1976) Acta Crystallogr B32:607

    CAS  Google Scholar 

  63. Etter MC, Urbañczyk-Lipkowska Z, Jahn DA, Frye JS (1986) J Am Chem Soc 108:5871

    Article  CAS  Google Scholar 

  64. Aoyama Y, Endo K, Anzai T, Yamaguchi Y, Sawaki T, Kobayashi K, Kanehisa N, Hashimoto H, Kai Y, Masuda H (1996) J Am Chem Soc 118:5562

    Article  CAS  Google Scholar 

  65. Endo K, Sawaki T, Koyanagi M, Kobayashi K, Masuda H, Aoyama Y (1995) J Am Chem Soc 117:8341

    Article  CAS  Google Scholar 

  66. Endo K, Koike T, Sawaki T, Hayashida O, Masuda H, Aoyama Y (1997) J Am Chem Soc 119:4117

    Article  CAS  Google Scholar 

  67. Felix O, Hosseini MW, DeCian A, Fischer J (1997) Angew Chem Int Ed Engl 36:102

    Article  CAS  Google Scholar 

  68. Desiraju GR (1997) J Chem Soc Chem Commun 1475

    Google Scholar 

  69. Desiraju GR (1991) Acc Chem Res 24:290

    Article  CAS  Google Scholar 

  70. Pauling L (1960) The nature of the chemical bond, 3rd edn. Cornell University Press, Ithaca

    Google Scholar 

  71. Dougill MW, Jeffrey GA (1953) Acta Crystallogr 6:831

    Article  CAS  Google Scholar 

  72. Taylor R, Kennard O (1982) J Am Chem Soc 104:5063

    Article  CAS  Google Scholar 

  73. Sharma CVK, Panneerselvam K, Pilati T, Desiraju GR (1992) J Chem Soc Chem Commun 832

    Google Scholar 

  74. Sharma CVK, Desiraju GR (1994) J Chem Soc Perkin Trans 2 2345

    Google Scholar 

  75. Reddy DS, Goud BS, Panneerselvam K, Desiraju GR (1993) J Chem Soc Chem Commun 663

    Google Scholar 

  76. Thalladi VR, Panneerselvam K, Carrell CJ, Carrell HL, Desiraju GR (1995) J Chem Soc Chem Commun 341

    Google Scholar 

  77. Reddy DS, Panneerselvam K, Pilati T, Desiraju GR (1993) J Chem Soc Chem Comm 661

    Google Scholar 

  78. Reddy DS, Ovchinnikov YE, Shishkin OV, Struchkov YT, Desiraju GR (1996) J Am Chem Soc 118:4085

    Article  CAS  Google Scholar 

  79. Pascal RA Jr, Ho DM (1992) Tetrahedron Lett 33:4707

    Article  CAS  Google Scholar 

  80. Xu K, Ho DM, Pascal RA Jr (1995) J Org Chem 60:7186

    Article  CAS  Google Scholar 

  81. Thalladi VR, Goud BS, Hoy VJ, Allen FH, Howard JAK, Desiraju GR (1996) J Chem Soc Chem Commun 401

    Google Scholar 

  82. Allen FH, Goud BS, Hoy VJ, Howard JAK, Desiraju GR (1994) J Chem Soc Chem Commun 2729

    Google Scholar 

  83. Sarma JARP, Allen FH, Hoy VJ, Howard JAK, Thaimattam R, Biradha K, Desiraju GR (1997) J Chem Soc Chem Commun 101

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Yale University, New Haven, CT, 06520-8107, USA

    Rosa E. Meléndez & Andrew D. Hamilton

Authors
  1. Rosa E. Meléndez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Andrew D. Hamilton
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Straße 29, 09596, Freiberg/Sachsen, Germany

    Edwin Weber

Rights and permissions

Reprints and permissions

Copyright information

© 1998 Springer Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Meléndez, R.E., Hamilton, A.D. (1998). Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs for Crystal Engineering. In: Weber, E., et al. Design of Organic Solids. Topics in Current Chemistry, vol 198. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69178-2_3

Download citation

  • DOI: https://doi.org/10.1007/3-540-69178-2_3

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-64645-7

  • Online ISBN: 978-3-540-69178-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation