Skip to main content

Multiporphyrin ArraysAssembled Through Hydrogen Bonding

  • Chapter
  • First Online:
Non-Covalent Multi-Porphyrin Assemblies

Part of the book series: Structure and Bonding ((STRUCTURE,volume 121))

Abstract

Although relatively weak in isolation, composite H-bonds can be used as an advantage for the assembly of relatively robust and well-defined arrays of molecular components. Porphyrins, with their inherent symmetry, synthetic accessibility and functionality offer ideal base units for the assembly of multicomponent systems by the reversible yet strong intermolecular forces of H-bonding. The geometric precision and strong directionality of H-bonds between relatively rigid donor and acceptor groups can be incorporated into the architecture of porphyrin supramolecular arrays to produce some remarkably complex high-definition assemblies through simple mixing of the component parts. Nevertheless, the very reversibility which allows for ease of construction becomes problematic in ensuring integrity of structure in solution; temperature, solvent and concentration become increasingly important. Measurement techniques are limited to those which can discriminate between the various possible combinations of the component parts to produce discrete oligomeric or polymeric entities. In many cases the measured properties of the assemblies underlying the reason for their construction in the first place also corroborate their structural integrity. Although H-bonding has been used to construct heterotopic porphyrinic arrays comprising porphyrins integrated with other molecular entities, this review is constrained to those systems which principally result in multiporphyrin arrays, although often templated by non-porphyrinic component parts.

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

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Desiraju GR (2002) Acc Chem Research 35:565

    Article  CAS  Google Scholar 

  2. Steiner T (2002) Angew Chem Int Ed Engl 41:48

    Article  CAS  Google Scholar 

  3. Schmuck C, Wienand W (2001) Angew Chem Int Ed Engl 40:4363

    Article  CAS  Google Scholar 

  4. Archer EA, Gong HG, Krische MJ (2001) Tetrahedron 57:1139

    Article  CAS  Google Scholar 

  5. Subramanian S, Zaworotko MJ (1994) Coord Chem Rev 137:357

    Article  CAS  Google Scholar 

  6. Aakeroy CB, Seddon KR (1993) Chem Soc Rev 22:397

    Article  CAS  Google Scholar 

  7. Prins LJ, Reinhoudt DN, Timmerman P (2001) Angew Chem Int Ed Engl 40:2382

    Article  CAS  Google Scholar 

  8. Turner DR, Pastor A, Alajarin M, Steed JW (2004) In: Michael D, Mingos P (eds) Structure and Bonding, vol 108. Springer, Berlin Heidelberg New York, p 97

    Google Scholar 

  9. Vilar R (2004) In: Michael D, Mingos P (eds) Structure and Bonding, vol 111. Springer, Berlin Heidelberg New York, p 85

    Google Scholar 

  10. Hardie MJ (2004) In: Michael D, Mingos P (eds) Structure and Bonding, vol 111. Springer, Berlin Heidelberg New York, p 139

    Google Scholar 

  11. Burrows AD (2004) In: Michael D, Mingos P (eds) Structure and Bonding, vol 108. Springer, Berlin Heidelberg New York, p 55

    Google Scholar 

  12. Aliev AE, Harris KDM (2004) In: Michael D, Mingos P (eds) Structure and Bonding, vol 108. Springer, Berlin Heidelberg New York, p 1

    Google Scholar 

  13. Shi X, Barkigia KM, Fajer J, Drain CM (2001) J Org Chem 66:6513

    Article  CAS  Google Scholar 

  14. Balaban Teodor S, Eichhöfer A, Lehn J-M (2000) Eur J Org Chem 24:4047

    Article  Google Scholar 

  15. Bhyrappa P, Wilson SR, Suslick KS (1997) J Am Chem Soc 119:8492

    Article  CAS  Google Scholar 

  16. Suslick KS, Bhyrappa P, Chou JH, Kosal ME, Nakagaki S, Smithenry DW, Wilson SR (2005) Acc Chem Research 38:283

    Article  CAS  Google Scholar 

  17. Kosal ME, Suslick KS (2000) J Solid State Chem 152:87

    Article  CAS  Google Scholar 

  18. Suslick KS, Kosal ME, Bhyrappa P (1998) Abstr Pap Am Chem Soc 216:290

    Google Scholar 

  19. Satake A, Kobuke Y (2005) Tetrahedron 61:13

    Article  CAS  Google Scholar 

  20. Ogawa K, Kobuke Y (2004) In: Nalwa HS (ed) Encyclopedia of Nanoscience and Nanotechnology, vol 9. American Scientific Publishers, Stevenson Ranch, California, p 561

    Google Scholar 

  21. Chen X, Drain CM (2004) In: Nalwa HS (ed) Encyclopedia of Nanoscience and Nanotechnology, vol 9. American Scientific Publishers, Stevenson Ranch, California, p 593

    Google Scholar 

  22. Turró C, Chang CK, Leroi GE, Cukier RI, Nocera DG (1992) J Am Chem Soc 114:4013

    Article  Google Scholar 

  23. Kuroda Y, Sugou K, Sasaki K (2000) J Am Chem Soc 122:7833

    Article  CAS  Google Scholar 

  24. Kuroda Y, Kawashima A, Hayashi Y, Ogoshi H (1997) J Am Chem Soc 119:4929

    Article  CAS  Google Scholar 

  25. Sugou K, Sasaki K, Kitajima K, Iwaki T, Kuroda Y (2002) J Am Chem Soc 124:1182

    Article  CAS  Google Scholar 

  26. Yamaguchi T, Ishii N, Tashiro K, Aida T (2003) J Am Chem Soc 125:13934

    Article  CAS  Google Scholar 

  27. Otsuki J, Iwasaki K, Nakano Y, Itou M, Araki Y, Ito O (2004) Chem Eur J 10:3461

    Article  CAS  Google Scholar 

  28. Ikeda C, Yoon ZS, Park M, Inoue H, Kim D, Osuka A (2005) J Am Chem Soc 127:534

    Article  CAS  Google Scholar 

  29. Ikeda C, Nagahara N, Motegi E, Yoshioka N, Inoue H (1999) Chem Commun 17:1759

    Article  Google Scholar 

  30. Harriman A, Magda DJ, Sessler JL (1991) J Phys Chem 95:1530

    Article  CAS  Google Scholar 

  31. Harriman A, Magda DJ, Sessler JL (1991) Chem Commun :345

    Google Scholar 

  32. Sessler JL, Wang B, Harriman A (1995) J Am Chem Soc 117:704

    Article  CAS  Google Scholar 

  33. Slobodkin G, Fan E, Hamilton AD (1992) New J Chem 16:643

    CAS  Google Scholar 

  34. Hamilton AD (1995) Tetrahedron 51(2):343

    Article  Google Scholar 

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

    Google Scholar 

  36. Drain CM, Russell KC, Lehn J-M (1996) Chem Commun 3:337

    Article  Google Scholar 

  37. Sessler JL, Jayawickramarajah J (2005) Chem Commun 15:1939

    Article  CAS  Google Scholar 

  38. Endo M, Seeman NC, Majima T (2005) Angew Chem Int Ed 44:6074

    Article  CAS  Google Scholar 

  39. Endo M, Shiroyama T, Fujitsuka M, Majima T (2005) J Org Chem 70:7468

    Article  CAS  Google Scholar 

  40. Bouamaied I, Stulz E (2005) Synlett 9:1579

    Google Scholar 

  41. Bouamaied I, Stulz E (2005) Chimia 59:101

    Article  CAS  Google Scholar 

  42. Bouamaied I, Fendt L-A, Stulz E (2005) private communication

    Google Scholar 

  43. Shao X-B, Jiang X-K, Zhu S-Z, Li Z-T (2004) Tetrahedron 60:9155

    Article  CAS  Google Scholar 

  44. Calama MC, Timmerman P, Reinhoudt DN (2000) Angew Chem Int Ed 39:755

    Article  CAS  Google Scholar 

  45. Calama MC, Timmerman P, Reinhoudt DN, Hulst R, Timmerman P, Fokkens R, Nibbering NMM (1998) Chem Commun 9:1021

    Article  Google Scholar 

  46. Paraschiv V, Crego-Calama M, Fokkens RH, Padberg CJ, Timmermann P, Reinhoudt DN (2001) J Org Chem 66:8297

    Article  CAS  Google Scholar 

  47. Ogoshi H, Mizutani T, Hayashi T, Kuroda Y (2000) In: Kadish KM, Smith KM, Guilard R (eds) The Porphyrin Handbook, vol 6. Academic Press, San Diego, p 279

    Google Scholar 

  48. Chambron J-C, Heitz V, Sauvage J-P (2000) In: Kadish KM, Smith KM, Guilard R (eds) The Porphyrin Handbook, vol 6. Academic Press, San Diego, p 1

    Google Scholar 

  49. Gunter MJ (2004) Eur J Org Chem :1655

    Article  CAS  Google Scholar 

  50. Gunter MJ, Jeynes TP, Turner P (2004) Eur J Org Chem :193

    Article  CAS  Google Scholar 

  51. Gunter MJ, Farquhar SM (2003) Org Biomol Chem 1:3450

    Article  CAS  Google Scholar 

  52. Gunter MJ, Bampos N, Johnstone KD, Sanders JKM (2001) New J Chem 25:166

    Article  CAS  Google Scholar 

  53. Schalley CA, Beizai K, Vogtle F (2001) Acc Chem Research 34:465

    Article  CAS  Google Scholar 

  54. Breault GA, Hunter CA, Mayers PC (1999) Tetrahedron 55:5265

    Article  CAS  Google Scholar 

  55. Gunter MJ, Farquhar SM, Mullen KM (2004) New J Chem 28:1443

    CAS  Google Scholar 

  56. Nagata N, Kugimiya S-I, Kobuke Y (2000) Chem Commun 15:1389

    Article  Google Scholar 

  57. Nagata N, Kugimiya S-I, Kobuke Y (2001) Chem Commun 8:689

    Article  Google Scholar 

  58. Tamaru S-I, Nakamura M, Takeuchi M, Shinkai S (2001) Org Lett 3:3631

    Article  CAS  Google Scholar 

  59. Tanaka S, Shirakawa M, Kaneko K, Takeuchi M, Shinkai S (2005) Langmuir 21:2163

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Maxwell J Gunter .

Editor information

Enzo Alessio

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Gunter, M.J. Multiporphyrin ArraysAssembled Through Hydrogen Bonding. In: Alessio, E. (eds) Non-Covalent Multi-Porphyrin Assemblies. Structure and Bonding, vol 121. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_020

Download citation

Publish with us

Policies and ethics