Copper Complexes of Star-Shaped Cholic Acid Oligomers With 1,2,3-Triazole Moieties

  • Matthias J. N. Junk
Part of the Springer Theses book series (Springer Theses)


Oligomers based on cholic acid are known to form hydrophobic cavities in hydrophilic solvents due to the facial amphiphilicity of their building blocks. In such pockets, non-polar molecules such as pyrene can be hosted. Oligomers with 1,2,3-triazole moieties are also able to coordinate heavy metal ions. Depending on their position in the cholic acid oligomer, the triazole groups may either cooperatively bind to the metal ion in analogy to a tridentate ligand or act as single entities.


Cholic Acid Hyperfine Coupling Electron Spin Echo Envelope Modulation Pyrene Molecule HYSCORE Spectrum 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. 1.
    Mukhopadhyay S, Maitra U (2004) Curr Sci 87:1666–1683Google Scholar
  2. 2.
    Benrebouh A, Avoce D, Zhu XX (2001) Polymer 42:4031–4038CrossRefGoogle Scholar
  3. 3.
    Fu H-L, Cheng S-X, Zhang X-Z, Zhuo R-X (2007) J Controlled Release 124:181–188CrossRefGoogle Scholar
  4. 4.
    Gauthier M, Simard P, Zhang Z, Zhu XX (2007) J R Soc Interface 4:1145–1150CrossRefGoogle Scholar
  5. 5.
    Zhang J, Zhu XX (2009) Sci Chin Ser B: Chem 52:849–861CrossRefGoogle Scholar
  6. 6.
    Zhu XX, Nichifor M (2002) Acc Chem Res 35:539–546CrossRefGoogle Scholar
  7. 7.
    Vijayalakshmi N, Maitra U (2006) J Org Chem 71:768–774CrossRefGoogle Scholar
  8. 8.
    Zhong ZQ, Zhao Y (2007) Org Lett 9:2891–2894CrossRefGoogle Scholar
  9. 9.
    Whitmarsh SD, Redmond AP Sgarlata V, Davis AP (2008) Chem Commun 3669–3671Google Scholar
  10. 10.
    Janout V, Lanier M, Regen SL (1996) J Am Chem Soc 118:1573–1574CrossRefGoogle Scholar
  11. 11.
    Janout V, Zhang LH, Staina IV, Di Giorgio C, Regen SL (2001) J Am Chem Soc 123:5401–5406CrossRefGoogle Scholar
  12. 12.
    Janout V, Jing BW, Regen SL (2002) Bioconjugate Chem 13:351–356CrossRefGoogle Scholar
  13. 13.
    Janout V, Jing BW, Staina IV, Regen SL (2003) J Am Chem Soc 125:4436–4437CrossRefGoogle Scholar
  14. 14.
    Janout V, Regen SL (2005) J Am Chem Soc 127:22–23CrossRefGoogle Scholar
  15. 15.
    Janout V, Jing BW, Regen SL (2005) J Am Chem Soc 127:15862–15870CrossRefGoogle Scholar
  16. 16.
    Janout V, Regen SL (2009) Bioconjugate Chem 20:183–192CrossRefGoogle Scholar
  17. 17.
    Zhao Y, Ryu EH (2005) J Org Chem 70:7585–7591CrossRefGoogle Scholar
  18. 18.
    Ryu EH, Yan J, Zhong Z, Zhao Y (2006) J Org Chem 71:7205–7213CrossRefGoogle Scholar
  19. 19.
    Ryu EH, Zhao Y (2004) Org Lett 6:3187–3189CrossRefGoogle Scholar
  20. 20.
    Ryu EH, Zhao Y (2006) J Org Chem 71:9491–9494CrossRefGoogle Scholar
  21. 21.
    Mukhopadhyay S, Maitra U, Ira, Krishnamoorthy G, Schmidt J, Talmon Y (2004) J Am Chem Soc 126:15905–15914CrossRefGoogle Scholar
  22. 22.
    Maitra U, Mukhopadhyay S, Sarkar A, Rao P, Indi SS (2001) Angew Chem Int Ed 40:2281–2283CrossRefGoogle Scholar
  23. 23.
    Luo J, Chen Y, Zhu XX (2007) Synlett 2201–2204Google Scholar
  24. 24.
    Luo J, Chen Y, Zhu XX (2009) Langmuir 25:10913–10917CrossRefGoogle Scholar
  25. 25.
    Zhang J, Luo J, Zhu XX, Junk MJN, Hinderberger D (2010) Langmuir 26:2958–2962CrossRefGoogle Scholar
  26. 26.
    Chen Y, Luo J, Zhu XX (2008) J Phys Chem B 112:3402–3409CrossRefGoogle Scholar
  27. 27.
    Tornoe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057–3064CrossRefGoogle Scholar
  28. 28.
    Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596–2599CrossRefGoogle Scholar
  29. 29.
    Bock VD, Hiemstra H, van Maarseveen JH (2005) Eur J Org Chem 1:51–68Google Scholar
  30. 30.
    Kalyanasundaram K, Thomas JK (1977) J Am Chem Soc 99:2039–2044CrossRefGoogle Scholar
  31. 31.
    Lakowicz JR (1999) Principles of fluorescence spectroscopy. Springer, BerlinGoogle Scholar
  32. 32.
    Assour JM (1965) J Chem Phys 43:2477–2489CrossRefGoogle Scholar
  33. 33.
    Stankowski J, Wieckowski A, Hedewy S (1974) J Magn Reson 15:498–509CrossRefGoogle Scholar
  34. 34.
    Bohandy J, Kim BF (1977) J Magn Reson 26:341–349CrossRefGoogle Scholar
  35. 35.
    Cunningham KL, McNett KM, Pierce RA, Davis KA, Harris HH, Falck DM, McMillin DR (1997) Inorg Chem 36:608–613CrossRefGoogle Scholar
  36. 36.
    van Koningsbruggen PJ, van Hal JW, de Graaff RAG, Haasnoot JG, Reedijk J (1993) J Chem Soc Dalton Trans 2163–2167Google Scholar
  37. 37.
    van Koningsbruggen PJ, Gatteschi D, Degraaff RAG, Haasnoot JG, Reedijk J, Zanchini C (1995) Inorg Chem 34:5175–5182CrossRefGoogle Scholar
  38. 38.
    Lu J, Bender CJ, McCracken J, Peisach J, Severns JC, McMillin DR (1992) Biochemistry 31:6265–6272CrossRefGoogle Scholar
  39. 39.
    Place C, Zimmermann J-L, Mulliez E, Guillot G, Bois C, Chottard J-C (1998) Inorg Chem 37:4030–4039CrossRefGoogle Scholar
  40. 40.
    Burns CS, Aronoff-Spencer E, Dunham CM, Lario P, Avdievich NI, Antholine WE, Olmstead MM, Vrielink A, Gerfen GJ, Peisach J, Scott WG, Millhauser GL (2002) Biochemistry 41:3991–4001CrossRefGoogle Scholar
  41. 41.
    Benesi HA, Hildebrand JH (1949) J Am Chem Soc 71:2703–2707CrossRefGoogle Scholar
  42. 42.
    Chang K-C, Su I-H, Senthilvelan A, Chung W-S (2007) Org Lett 9:3363–3366CrossRefGoogle Scholar
  43. 43.
    Lehn J-M (1995) Supramolecular Chemistry: concepts and perspectives. Wiley, New YorkCrossRefGoogle Scholar
  44. 44.
    Qi X, Jun EJ, Xu L, Kim S-J, Hong JSJ, Yoon YJ, Yoon J (2006) J Org Chem 71:2881–2884CrossRefGoogle Scholar
  45. 45.
    Xiang Y, Tong A, Jin P, Ju Y (2006) Org Lett 8:2863–2866CrossRefGoogle Scholar
  46. 46.
    Park SM, Kim MH, Choe J-I, No KT, Chang S-K (2007) J Org Chem 72:3550–3553CrossRefGoogle Scholar
  47. 47.
    Huang S, Clark RJ, Zhu L (2007) Org Lett 9:4999–5002CrossRefGoogle Scholar
  48. 48.
    Moon SY, Youn NJ, Park SM, Chang SK (2005) J Org Chem 70:2394–2397CrossRefGoogle Scholar
  49. 49.
    Zhao Y, Zhong Z (2006) Org Lett 8:4715–4717CrossRefGoogle Scholar
  50. 50.
    Hung H-C, Cheng C-W, Ho I-T, Chung W-S (2009) Tetrahedron Lett 50:302–305CrossRefGoogle Scholar
  51. 51.
    Zhu L, dos Santos O, Koo CW, Rybstein M, Pape L, Canary JW (2003) Inorg Chem 42:7912–7920CrossRefGoogle Scholar
  52. 52.
    Richeter S, Rebek J (2004) J Am Chem Soc 126:16280–16281CrossRefGoogle Scholar
  53. 53.
    Parkin G (2004) Chem Rev 104:699–767CrossRefGoogle Scholar
  54. 54.
    Schweiger A, Jeschke G (2001) Principles of pulse electron paramagnetic resonance. Oxford University Press, OxfordGoogle Scholar
  55. 55.
    Weil JA, Bolton JR, Wertz JE (1994) Electron paramagnetic resonance: elementary theory and practical applications. Wiley, New YorkGoogle Scholar
  56. 56.
    Iwaizumi M, Ohba Y, Iida H, Hirayama M (1984) Inorg Chim Acta 82:47–52CrossRefGoogle Scholar
  57. 57.
    Zhang J (2010) 基于胆酸的分子篮的合成与性质表征 (The synthesis and properties of molecular pockets based on cholic acid). Doctoral Dissertation, Nankai University, TianjinGoogle Scholar
  58. 58.
    Schweiger A (1991) Angew Chem Int Ed 30:265–292CrossRefGoogle Scholar
  59. 59.
    Höfer P, Grupp A, Nebenführ H, Mehring M (1986) Chem Phys Lett 132:279–282CrossRefGoogle Scholar
  60. 60.
    Jiang F, McCracken J, Peisach J (1990) J Am Chem Soc 112:9035–9044CrossRefGoogle Scholar
  61. 61.
    Slutter CE, Gromov I, Epel B, Pecht I, Richards JH, Goldfarb D (2001) J Am Chem Soc 123:5325–5336CrossRefGoogle Scholar
  62. 62.
    Stoll S, Schweiger A (2006) J Magn Reson 178:42–55CrossRefGoogle Scholar
  63. 63.
    Madi ZL, Van Doorslaer S, Schweiger A (2002) J Magn Reson 154:181–191CrossRefGoogle Scholar
  64. 64.
    Milov AD, Salikhov KM, Shirov MD (1981) Fiz Tverd Tela 23:975–982Google Scholar
  65. 65.
    Pannier M, Veit S, Godt A, Jeschke G, Spiess HW (2000) J Magn Reson 142:331–340CrossRefGoogle Scholar
  66. 66.
    Jeschke G, Pannier M, Spiess HW (2000) Double electron–electron resonance. In: Berliner LJ, Eaton GR, Eaton SS (eds) Biological magnetic resonance, Distance measurements in biological systems by EPR, vol 19. Kluwer Academic, New YorkGoogle Scholar
  67. 67.
    Jeschke G, Chechik V, Ionita P, Godt A, Zimmermann H, Banham J, Timmel CR, Hilger D, Jung H (2006) Appl Magn Reson 30:473–498CrossRefGoogle Scholar
  68. 68.
    Zhang J, Junk MJN, Luo J, Hinderberger D, Zhu XX (2010) Langmuir 26:13415–13421CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2012

Authors and Affiliations

  1. 1.Max Planck Institute for Polymer ResearchMainzGermany

Personalised recommendations