A novel porphyrin based fluorescent chemosensor using a molecular recognition approach

Abstract

Free-base porphyrin covalently linked to quinone exhibits enhanced fluorescence on coupling the quinone with hydroquinone, primarily due to the unfavourable conditions for an electron transfer reaction between the singlet excited porphyrin and the newly formed quinone–hydroquinone entity.

References

1. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; L. R. Sousa, B. Valeur, A. P. de Silva, Bouas, H. Laurent, A. Ueno, T. Bell, R. Y. Tsien, M. Kuhn, D. Masilamani and G. Krafft, in Fluorescent Chemosensors for Ion and Molecule Recognition, ed. A. W. Czarnk, American Chemical Society, Washington DC, 1993; R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy and K. R. A. S. Sandanayake, Top. Curr. Chem., 1993, 168, 223.
2. L. R. Sousa and J. M. Larson, J. Am. Chem. Soc., 1977, 99, 307; P. Nanjappan and A. W. Czarnik, J. Am. Chem. Soc., 1987, 109, 1826; M. Houston, K. Haider and A. W. Czarnik, J. Am. Chem. Soc., 1988, 110, 4460; A. P. de Silva and S. A. de Silva, J. Chem. Soc., Chem. Commun., 1986, 1709; E. U. Akkaya, M. E. Houston and A. W. Czarnik, J. Am. Chem. Soc., 1990, 112, 3590; M. E. Houston and A. W. Czarnik, J. Am. Chem. Soc., 1990, 112, 7054; M.-Y. Chae and A. W. Czarnik, J. Am. Chem. Soc., 1992, 114, 9704; M.-Y. Chae, X. M. Cherian and A. W. Czarnik, J. Org. Chem., 1993, 58, 5797; H. A. Godwin and J. M. Berg, J. Am. Chem. Soc., 1996, 118, 6514; G. K. Walkup and G. Imperiali, J. Am. Chem. Soc., 1996, 118, 3053.
3. M. E. Houston, E. U. Akkaya and A. W. Czarnik, J. Am. Chem. Soc., 1989, 111, 8735; D. H. Vance and A. W. Czarnik, J. Am. Chem. Soc., 1994, 116, 9397.
4. J.-Y. Yoon and A. W. Czarnik, J. Am. Chem. Soc., 1992, 114, 5874; J.-Y. Yoon and A. W. Czarnik, Bioorg. Med. Chem., 1993, 1, 267; R. Grigg and W. D. J. A. Morbert, J. Chem. Soc., Chem. Commun., 1992, 1298; P. Tecilla, R. P. Dixon, G. Slobodkin, D. S. Alavi and D. H. Waldeck, J. Am. Chem. Soc., 1990, 112, 9408; A. Harriman, Y. Kubo and J. A. Sessler, J. Am. Chem. Soc., 1992, 114, 388; T. Hayashi, T. Miyahara, N. Hashizume and H. Ogoshi, J. Am. Chem. Soc., 1993, 114, 2049.
5. F. D'Souza, J. Am. Chem. Soc., 1996, 118, 923.
6. K. Wynne, S. M. LeCours, C. Galli, M. J. Therien and R. M. Hochstrasser, J. Am. Chem. Soc., 1995, 117, 3749.
7. J. Dalton and L. R. Milgrom, J. Chem. Soc., Chem. Commun., 1979, 609; M. A. Bergkamp, J. Dalton and T. L. Netzel, J. Am. Chem. Soc., 1982, 104, 253.
8. P. G. Seybold and M. Gouterman, J. Mol. Spectrosc., 1969, 31, 1; D. J. Quimby and F. R. Longo, J. Am. Chem. Soc., 1975, 97, 5111.
9. A. Austin and M. Gouterman, Bioinorg. Chem., 1978, 9, 281.
10. D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 529.
11. R. A. Bissell, A. P. De Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire and D. R. A. S. Sandanayake, Chem. Soc. Rev., 1992, 21, 187.
12. M. A. Slifkin and R. H. Walmsley, Spectrochim. Acta, 1970, 26A, 1237; M. Kubinyi and G. Keresztury, Spectrochim. Acta, 1989, 45A, 421.
13. J. Q. Chambers, in The Chemistry of Quinonoid Compounds, ed. S. Patai, Wiley, New York, 1974, ch. 14.
14. K. M. Kadish, Prog. Inorg. Chem., 1986, 34, 435.