Advertisement

From Phosphorus-Containing Macrocycles to Phosphorus-Containing Dendrimers

  • Anne-Marie CaminadeEmail author
  • Jean-Pierre Majoral
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 20)

Abstract

Various methods of synthesis of phosphorus-containing macrocycles are described. They are obtained in good to quantitative yields, thanks to the presence of phosphorhydrazone (P–N–N=) linkages in their structure. Multi-macrocyclic species and cryptands possessing the same linkage are also described. Various types of reactions, including complexation properties of the macrocycles are also reviewed. In the last part, the use of the same linkage for the elaboration of phosphorus-containing dendrimers is described, with emphasis on dendrimers incorporating macrocycles in some part of their structure (terminal groups, core or interior).

Keywords

Cryptand Dendrimer Macrocycle Phosphorhydrazone Phosphorus 

References

  1. 1.
    Stokes HN (1897) Am Chem J 19:782CrossRefGoogle Scholar
  2. 2.
    Pedersen CJ (1967) J Am Chem Soc 89:7017CrossRefGoogle Scholar
  3. 3.
    Caminade AM, Majoral JP (1994) Chem Rev 94:1183CrossRefGoogle Scholar
  4. 4.
    Hua G, Li Y, Slawin AMZ, Woollins JD (2008) Angew Chem Int Ed 47:2857CrossRefGoogle Scholar
  5. 5.
    Gonzales-Calera S, Eisler DJ, Morey JV, McPartlin M, Wright DS (2008) Angew Chem Int Ed 47:1111CrossRefGoogle Scholar
  6. 6.
    Matano Y, Miyajima T, Nakabuchi T, Imahori H, Ochi N, Sakaki S (2006) J Am Chem Soc 128:11760CrossRefGoogle Scholar
  7. 7.
    Theil A, Mauve C, Adeline MT, Marinetti A, Sauvage JP (2006) Angew Chem Int Ed 45:2104CrossRefGoogle Scholar
  8. 8.
    Majoral JP, Badri M, Caminade AM, Delmas M, Gaset A (1988) Inorg Chem 27:3873CrossRefGoogle Scholar
  9. 9.
    Galliot C, Caminade AM, Dahan F, Majoral JP (1993) Angew Chem Int Ed Engl 32:1477CrossRefGoogle Scholar
  10. 10.
    Colombo-Khater D, He Z, Caminade AM, Dahan F, Kraemer R, Majoral JP (1993) Synthesis 1145Google Scholar
  11. 11.
    Majoral JP, Kraemer R, Navech J, Mathis F (1976) Tetrahedron 32:2633CrossRefGoogle Scholar
  12. 12.
    Mitjaville J, Caminade AM, Mathieu R, Majoral JP (1994) J Am Chem Soc 116:5007CrossRefGoogle Scholar
  13. 13.
    Mitjaville J, Caminade AM, Majoral JP (1995) Synthesis 952Google Scholar
  14. 14.
    Badri M, Majoral JP, Caminade AM, Delmas M, Gaset A, Gorgues A, Jaud J (1990) J Am Chem Soc 112:5618CrossRefGoogle Scholar
  15. 15.
    Oussaid B, Garrigues B, Caminade AM, Majoral JP (1992) Phosphorus Sulfur Silicon 73:41CrossRefGoogle Scholar
  16. 16.
    Oussaid B, Garrigues B, Jaud J, Caminade AM, Majoral JP (1993) J Org Chem 58:4500CrossRefGoogle Scholar
  17. 17.
    Majoral JP, Badri M, Caminade AM, Gorgues A, Delmas M, Gaset A (1990) Phosphorus Sulfur Silicon 49–50:413CrossRefGoogle Scholar
  18. 18.
    Badri M, Majoral JP, Gonce F, Caminade AM, Sallé M, Gorgues A (1990) Tetrahedron Lett 31:6343CrossRefGoogle Scholar
  19. 19.
    Launay N, Denat F, Caminade AM, Majoral JP, Dubac J (1994) Bull Soc Chim Fr 131:758Google Scholar
  20. 20.
    Chandrasekhar V, Andavan GTS, Azhakar R, Pandian BM (2007) Synth React Inorg Met Org Nano-Met Chem 37:725Google Scholar
  21. 21.
    Chandrasekhar V, Andavan GTS, Azhakar R, Pandian BM (2004) Tetrahedron Lett 47:8365CrossRefGoogle Scholar
  22. 22.
    Gonce F, Caminade AM, Majoral JP (1991) Tetrahedron Lett 32:203CrossRefGoogle Scholar
  23. 23.
    Colombo D, Caminade AM, Majoral JP (1991) Inorg Chem 30:3365CrossRefGoogle Scholar
  24. 24.
    Prévoté D, Galliot C, Caminade AM, Majoral JP (1995) Heteroatom Chem 6:313CrossRefGoogle Scholar
  25. 25.
    Galliot C, Caminade AM, Majoral JP, Kuznikowski M, Zablocka M, Pietrusiewicz KM (1995) Chem Ber 128: 443CrossRefGoogle Scholar
  26. 26.
    Gonce F, Caminade AM, Boutonnet F, Majoral JP (1992) J Org Chem 57:970CrossRefGoogle Scholar
  27. 27.
    Mitjaville J, Caminade AM, Daran JC, Donnadieu B, Majoral JP (1995) J Am Chem Soc 117:1712CrossRefGoogle Scholar
  28. 28.
    Gonce F, Caminade AM, Jaud J, Vignaux P, Majoral JP (1992) Bull Soc Chim Fr 129:237Google Scholar
  29. 29.
    Majoral JP, Caminade AM (1992) The chemistry of inorganic ring systems. In: Steudel R (ed) Studies in Inorganic Chemistry, vol. 14, chap. 12. Elsevier Science, Amsterdam, p 209Google Scholar
  30. 30.
    Colombo-Khater D, Caminade AM, Delavaux-Nicot B, Majoral JP (1993) Organometallics 12:2861CrossRefGoogle Scholar
  31. 31.
    Caminade AM, Colombo-Khater D, Mitjaville J, Galliot C, Mas P, Majoral JP (1993) Phosphorus Sulfur Silicon 75:67CrossRefGoogle Scholar
  32. 32.
    Richelme S, Claparols C, Leroy E, Caminade AM, Munoz A (2000) Phosphorus Sulfur Silicon 161:143CrossRefGoogle Scholar
  33. 33.
    Curtis NF (1968) Coord Chem Rev 3:3CrossRefGoogle Scholar
  34. 34.
    Majoral JP, Caminade AM, Igau A (1994) In: Quin LD, Verkade JG (eds) Phosphorus-31 NMR spectral properties in compound characterization and structural analysis, chap. 5. VCH, Deerfield Beach, FL, USA, p 57Google Scholar
  35. 35.
    Caminade AM, Majoral JP (1996) Synlett 1019Google Scholar
  36. 36.
    Majoral JP, Badri M, Caminade AM (1991) Heteroatom Chem 2:45CrossRefGoogle Scholar
  37. 37.
    Galliot C, Caminade AM, Dahan F, Majoral JP (1993) Angew Chem Int Ed Engl 32:1477CrossRefGoogle Scholar
  38. 38.
    Majoral JP, Badri M, Caminade AM, Delmas M, Gaset A (1991) Inorg Chem 30:344CrossRefGoogle Scholar
  39. 39.
    Omelanczuk J (1992) J Chem Soc Chem Commun 1718Google Scholar
  40. 40.
    Galliot C, Larré C, Caminade AM, Majoral JP (1997) Science 277:1981CrossRefGoogle Scholar
  41. 41.
    Magro G, Caminade AM, Majoral JP (2003) Tetrahedron Lett 44:7007CrossRefGoogle Scholar
  42. 42.
    Staudinger H, Hauser E (1921) Helv Chim Acta 4:861CrossRefGoogle Scholar
  43. 43.
    Merino S, Brauge L, Caminade AM, Majoral JP, Taton D, Gnanou Y (2001) Chem Eur J 7:3095CrossRefGoogle Scholar
  44. 44.
    Turrin CO, Maraval A, Magro G, Maraval V, Caminade AM, Majoral JP (2006) Eur J Inorg Chem 2556Google Scholar
  45. 45.
    Caminade AM, Kraemer R, Majoral JP (1996) Inorg Chim Acta 246:47CrossRefGoogle Scholar
  46. 46.
    Badri M, Caminade AM, Majoral JP, Gorgues A (1991) Phosphorus Sulfur Silicon 56:123CrossRefGoogle Scholar
  47. 47.
    Kraemer R, Galliot C, Mitjaville J, Caminade AM, Majoral JP (1996) Heteroatom Chem 7:149CrossRefGoogle Scholar
  48. 48.
    Lehn JM (1978) Acc Chem Res 11:49CrossRefGoogle Scholar
  49. 49.
    Caminade AM, Kraemer R, Majoral JP (1997) New J Chem 21:627Google Scholar
  50. 50.
    Mitjaville J, Caminade AM, Majoral JP (1994) J Chem Soc Chem Commun 2161Google Scholar
  51. 51.
    Launay N, Caminade AM, Lahana R, Majoral JP (1994) Angew Chem Int Ed Engl 33:1589CrossRefGoogle Scholar
  52. 52.
    Lartigue ML, Donnadieu B, Galliot C, Caminade AM, Majoral JP, Fayet JP (1997) Macromolecules 30:7335CrossRefGoogle Scholar
  53. 53.
    Launay N, Caminade AM, Majoral JP (1997) J Organomet Chem 529:51CrossRefGoogle Scholar
  54. 54.
    Blais JC, Turrin CO, Caminade AM, Majoral JP (2000) Anal Chem 72:5097CrossRefGoogle Scholar
  55. 55.
    Launay N, Caminade AM, Majoral JP (1995) J Am Chem Soc 117:3282CrossRefGoogle Scholar
  56. 56.
    Launay N, Slany M, Caminade AM, Majoral JP (1996) J Org Chem 61:3799CrossRefGoogle Scholar
  57. 57.
    Prévôté D, Donnadieu B, Moreno-Manas M, Caminade AM, Majoral JP (1999) Eur J Org Chem 1701Google Scholar
  58. 58.
    Badetti E, Caminade AM, Majoral JP, Moreno-Manas M, Sebastian RM (2008) Langmuir 24:2090CrossRefGoogle Scholar
  59. 59.
    Le Derf F, Levillain E, Gorgues A, Sallé M, Sebastian RM, Caminade AM, Majoral JP (2001) Angew Chem Int Ed 40:224CrossRefGoogle Scholar
  60. 60.
    Leclaire J, Coppel Y, Caminade AM, Majoral JP (2004) J Am Chem Soc 126:2304CrossRefGoogle Scholar
  61. 61.
    Leclaire J, Dagiral R, Fery-Forgues S, Coppel Y, Donnadieu B, Caminade AM, Majoral JP (2005) J Am Chem Soc 127:15762CrossRefGoogle Scholar
  62. 62.
    Leclaire J, Dagiral R, Pla-Quintana A, Caminade AM, Majoral JP (2007) Eur J Inorg Chem 2890Google Scholar
  63. 63.
    Maszewska M, Leclaire J, Cieslak M, Nawrot B, Okruszek A, Caminade AM, Majoral JP (2003) Oligonucleotides 13:193CrossRefGoogle Scholar
  64. 64.
    Larpent C, Geniès C, De Sousa Delgado AP, Caminade AM, Majoral JP, Sassi JF, Leising F (2004) Chem Commun 1816Google Scholar
  65. 65.
    Merino S, Brauge L, Caminade AM, Majoral JP, Taton D, Gnanou Y (2001) Chem Eur J 7:3095CrossRefGoogle Scholar
  66. 66.
    Brauge L, Caminade AM, Majoral JP, Slomkowski S, Wolszczak M (2001) Macromolecules 34:5599CrossRefGoogle Scholar
  67. 67.
    Larré C, Caminade AM, Majoral JP (1997) Angew Chem Int Ed Engl 36:596CrossRefGoogle Scholar
  68. 68.
    Larré C, Donnadieu B, Caminade AM, Majoral JP (1998) J Am Chem Soc 120:4029CrossRefGoogle Scholar
  69. 69.
    Cadierno V, Igau A, Donnadieu B, Caminade AM, Majoral JP (1999) Organometallics 18:1580CrossRefGoogle Scholar
  70. 70.
    Larré C, Bressolles D, Turrin C, Donnadieu B, Caminade AM, Majoral JP (1998) J Am Chem Soc 120:13070CrossRefGoogle Scholar
  71. 71.
    Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) Polymer J 17:117CrossRefGoogle Scholar
  72. 72.
    Buhleier E, Wehner W, Vögtle F (1978) Synthesis 155Google Scholar
  73. 73.
    Hawker CJ, Fréchet JMJ (1990) J Am Chem Soc 112:7638CrossRefGoogle Scholar
  74. 74.
    Ouali A, Laurent R, Caminade AM, Majoral JP, Taillefer M (2006) J Am Chem Soc 128:15990CrossRefGoogle Scholar
  75. 75.
    Caminade AM, Majoral JP (2004) Accounts Chem Res 37:341CrossRefGoogle Scholar
  76. 76.
    Feng CL, Zhong XH, Steinhart M, Caminade AM, Majoral JP, Knoll W (2007) Adv Mater 19:1933CrossRefGoogle Scholar
  77. 77.
    Le Berre V, Trevisiol E, Dagkessamanskaia A, Sokol S, Caminade AM, Majoral JP, Meunier B, François J (2003) Nucl Acids Res 31:e88CrossRefGoogle Scholar
  78. 78.
    Krishna TR, Parent M, Werts MHV, Moreaux L, Gmouh S, Charpak S, Caminade AM, Majoral JP, Blanchard-Desce M (2006) Angew Chem Int Ed 45:4645CrossRefGoogle Scholar
  79. 79.
    Griffe L, Poupot M, Marchand P, Maraval A, Turrin CO, Rolland O, Métivier P, Bacquet G, Fournié JJ, Caminade AM, Poupot R, Majoral JP (2007) Angew Chem Int Ed 46:2523CrossRefGoogle Scholar

Copyright information

© Springer 2009

Authors and Affiliations

  1. 1.LCC (Laboratoire de Chimie de Coordination)Centre National de la Recherche Scientifique(CNRS)ToulouseFrance
  2. 2.Université de ToulouseUPS, INPT; LCCToulouseFrance

Personalised recommendations