Binding of porphyrins in cyclodextrin dimers

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 257-258

  Venema, Fokke ^a   Rowan, Alan E ^a   Nolte, Roeland J M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000856081     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952401y     Document Type: Article

References (19)

1. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
2. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
3. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
4. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
5. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
6. For other examples of porphyrins encapsulated in CDs, see: (a) Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341. (b) Manka, J. S.; Lawrence, D S. J. Am. Chem. Soc. 1990, 112, 2440. (c) Mosseri, S.; Mialocq, J. C.; Perly, B.; Hambright, P. J. Phys. Chem. 1991, 95, 2196. (d) Mosseri, S ; Mialocq, J. C.; Perly, B.; Hambrigh, P. J. Phys. Chem. 1991, 95, 4659. (e) Dick, D. L.; Venkata, T.; Rao, S.; Sukumaran, D.; Lawrence, D. S. J. Am Chem. Soc. 1992, 114, 2664. (f) Jiang, T.; Lawrence, D. S. J. Am. Chem. Soc. 1995, 117, 1857.
7. Venema, F.; Baselier, C. M.; van Dienst, E.; Ruël, B. H. M.; Feiters, M. C.; Engbersen, J. F. J.; Reinhoudt, D. N.; Nolte, R. J. M. Tetrahedron Lett. 1994, 35, 1773. It should be noted that the opening of the epoxide at C-3 leads to a cyclodextrin in which one of the glucose rings has undergone a flip to give an altrose ring; see: Breslow, R.; Czarnik, A. W. J. Am. Chem. Soc. 1983, 105, 1390.
8. Venema, F.; Baselier, C. M.; van Dienst, E.; Ruël, B. H. M.; Feiters, M. C.; Engbersen, J. F. J.; Reinhoudt, D. N.; Nolte, R. J. M. Tetrahedron Lett. 1994, 35, 1773. It should be noted that the opening of the epoxide at C-3 leads to a cyclodextrin in which one of the glucose rings has undergone a flip to give an altrose ring; see: Breslow, R.; Czarnik, A. W. J. Am. Chem. Soc. 1983, 105, 1390.
9. Fluorescence spectroscopy is more sensitive than UV/vis spectroscopy to study the aggregation of porphyrins: see also: (a) Margalit. R.; Shaklai, N.; Cohen, S. Biochem. J. 1983, 209, 547. (b) Ravikant, M.; Reddy, D.; Chandrashekar, K. J. Chem. Soc., Dalton Trans. 1991, 2103 and references cited therein.
10. Fluorescence spectroscopy is more sensitive than UV/vis spectroscopy to study the aggregation of porphyrins: see also: (a) Margalit. R.; Shaklai, N.; Cohen, S. Biochem. J. 1983, 209, 547. (b) Ravikant, M.; Reddy, D.; Chandrashekar, K. J. Chem. Soc., Dalton Trans. 1991, 2103 and references cited therein.
11. -6 M) used by the authors is in the aggregation range of the porphyrin, it is likely that they have observed the breakdown of porphyrin. aggregates. The reported binding constants are probably incorrect. Also the working mechanism for the reported complex as a chemosensor for pentachlorophenol is probably incorrect since this guest (size 9-10 Å) does not fit into a CD cavity (6-6.5 Å); see: Zhao, S.; Luong, J. H. T J. Chem. Soc., Chem. Commun. 1995, 663.
12. -6 M) used by the authors is in the aggregation range of the porphyrin, it is likely that they have observed the breakdown of porphyrin. aggregates. The reported binding constants are probably incorrect. Also the working mechanism for the reported complex as a chemosensor for pentachlorophenol is probably incorrect since this guest (size 9-10 Å) does not fit into a CD cavity (6-6.5 Å); see: Zhao, S.; Luong, J. H. T J. Chem. Soc., Chem. Commun. 1995, 663.
13. Breslow, R. Pure Appl. Chem. 1994, 66, 1573.
14. Venema, F.; Baselier, C. M.; Feiters, M. C.; Nolte, J. M. Tetrahedron Lett. 1994, 35, 8661.
15. The formation of an anti arrangement between 2a and β-CD was recently proposed by Ribó et al. based on ROESY spectra; see: Ribó, J. M.; Farrera, J.-A.; Valero, M. L.; Virgili, A. Tetrahedron 1995, 51, 3705.
16. -3 M.
17. -1.
18. To study the influence of Zn(II) ions, titrations of 2a with 1c were performed in 0.01 M Tris buffer, pH 7.0. The sigmoidal shape of the titration curve, which is observed in the absence of Zn(II) ions, was independent of the kind of buffer used (phosphate or Tris).
19. - counterions present.)