Exploitation of a novel 'on-off' photoinduced electron-transfer (PET) sensor against conventional 'off-on' PET sensors

Chemical Communications

Volumn , Issue 19, 1999, Pages 2011-2012

  Kijima, Hideomi ^a   Takeuchi, Masayuki ^a   Robertson, Andrew ^a   Shinkai, Seiji ^a   Cooper, Christopher ^b   James, Tony D ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

SUGAR; TETRAPHENYLPORPHYRIN DERIVATIVE; TIN DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; FLUORESCENCE; SENSOR;

EID: 0033533847     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906825b     Document Type: Article

References (21)

1. A. P. De Silva, H. Q. N. Gunarathe and C. P. McCoy, Chem. Commun., 1996, 2399; A. P. De Silva, H. Q. N. Gunarathe, C. McVeigh, G. E. M. Maguine, P. R. S. Maxwell and E. Q'Hanlon, Chem. Commun., 1996, 2191; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, C. P. McCoy, P. R. S. Maxwell, J. T. Rademacher and T. E. Rice, Pure Appl. Chem., 1996, 68, 1443; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515.
2. A. P. De Silva, H. Q. N. Gunarathe and C. P. McCoy, Chem. Commun., 1996, 2399; A. P. De Silva, H. Q. N. Gunarathe, C. McVeigh, G. E. M. Maguine, P. R. S. Maxwell and E. Q'Hanlon, Chem. Commun., 1996, 2191; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, C. P. McCoy, P. R. S. Maxwell, J. T. Rademacher and T. E. Rice, Pure Appl. Chem., 1996, 68, 1443; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515.
3. A. P. De Silva, H. Q. N. Gunarathe and C. P. McCoy, Chem. Commun., 1996, 2399; A. P. De Silva, H. Q. N. Gunarathe, C. McVeigh, G. E. M. Maguine, P. R. S. Maxwell and E. Q'Hanlon, Chem. Commun., 1996, 2191; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, C. P. McCoy, P. R. S. Maxwell, J. T. Rademacher and T. E. Rice, Pure Appl. Chem., 1996, 68, 1443; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515.
4. A. P. De Silva, H. Q. N. Gunarathe and C. P. McCoy, Chem. Commun., 1996, 2399; A. P. De Silva, H. Q. N. Gunarathe, C. McVeigh, G. E. M. Maguine, P. R. S. Maxwell and E. Q'Hanlon, Chem. Commun., 1996, 2191; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, C. P. McCoy, P. R. S. Maxwell, J. T. Rademacher and T. E. Rice, Pure Appl. Chem., 1996, 68, 1443; A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515.
5. A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; A. W. Czarnik, Fluorescent Chemosensors for Ion and Molecular Recognition, ACS Books, Washington, DC, 1993.
6. A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; A. W. Czarnik, Fluorescent Chemosensors for Ion and Molecular Recognition, ACS Books, Washington, DC, 1993.
7. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
8. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
9. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
10. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
11. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
12. T. D. James, K. R. A. S. Sandanayake and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 477; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; T. D. James, K. R. A. S. Sandanayake, R. Iguchi and S. Shinkai, J. Am. Chem. Soc., 1995, 117, 8982; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281; T. D. James, H. Shinmori, M. Takeuchi and S. Shinkai, Chem. Commun., 1996, 705; T. D. James, H. Shinmori and S. Shinkai, Chem. Commun., 1997, 71.
13. For comprehensive reviews, see: T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Supramol. Chem., 1995, 6, 141; K. R. A. S. Sandanayake, T. D. James and S. Shinkai, Pure Appl. Chem., 1996, 68, 281; S. Shinkai and M. Takeuchi, Trends Anal. Chem., 1996, 15, 188; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
14. For comprehensive reviews, see: T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Supramol. Chem., 1995, 6, 141; K. R. A. S. Sandanayake, T. D. James and S. Shinkai, Pure Appl. Chem., 1996, 68, 281; S. Shinkai and M. Takeuchi, Trends Anal. Chem., 1996, 15, 188; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
15. For comprehensive reviews, see: T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Supramol. Chem., 1995, 6, 141; K. R. A. S. Sandanayake, T. D. James and S. Shinkai, Pure Appl. Chem., 1996, 68, 281; S. Shinkai and M. Takeuchi, Trends Anal. Chem., 1996, 15, 188; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
16. For comprehensive reviews, see: T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Supramol. Chem., 1995, 6, 141; K. R. A. S. Sandanayake, T. D. James and S. Shinkai, Pure Appl. Chem., 1996, 68, 281; S. Shinkai and M. Takeuchi, Trends Anal. Chem., 1996, 15, 188; T. D. James, K. R. A. S. Sandanayake and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
17. More recently, Cooper and James reported a PET chemosensor with an anthracene fluorophore appending an o-aminomethylphenyl boronic acid group and a crown ether group which selectively binds glucosamine: C. R. Cooper and T. D. James, Chem. Commun., 1997, 1419.
18. It is known that the amino group is capable of quenching the fluorescence of the (tetraphenylporphinato)tin(IV) moiety: R. Grigg and W. D. J. A. Norkert, J. Chem. Soc., Chem. Commun., 1992, 1298.
19. Computer simulations were performed using CDiscover as implemented by Insight II ver. 98.0 on a Silicon Graphics Octane workstation. Conformations were explored with molecular dynamics simulations using the ESFF forcefield at 500 K for 40 ps with subsequent minimisation of low energy conformations.
20. C. R. Cooper, N. Spencer and T. D. James, Chem. Commun., 1998, 1365.
21. An alternative mechanism was briefly considered after mass spectrometry consistently demonstrated the loss of one chloride ligand during measurements. Although this phenomenon could result simply from losing chloride to achieve a positive charge, we also considered the possibility of displacement of chloride by a boron-attached oxygen to yield a B-O-Sn self-complexed macrocycle. IR and NMR experiments produced no evidence for this interaction, however, and it was therefore discarded.