Photophysical Studies of Some 5,10,15,20-Tetraarylethynylporphyrinatozinc(II) Complexes as Potential Lead Compounds for Photodynamic Therapy

Photochemistry and Photobiology

Volumn 67, Issue 1, 1998, Pages 97-100

  Lacey, Jackie A ^a   Phillips, David ^a   Milgrom, Lionel R ^a   Yahioglu, Gokhan ^a   Rees, Robert D ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b BRUNEL UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002716113     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb05170.x     Document Type: Article

References (30)

1. Wagner, R. W. and J. S. Lindsey (1994) A molecular photonic wire. J. Am. Chem. Soc. 116, 9759-9760.
2. Anderson, H. L. (1994) Conjugated porphyrin ladders. Inorg. Chem. 33, 972-981.
3. Arnold, D. P. and L. J. Nitschinsk (1992) Porphyrin dimers linked by conjugated butadiynes. Tetrahedron 48, 8781-8792.
4. LeCours, S. M., H.-W. Guan, S. G. DiMagno, C. H. Wang and M. J. Therien (1996) Push-pull arylethynylporphyrins: new chromophores that exhibit large molecular first order hyperpolarisibilities. J. Am. Chem. Soc. 118, 1497-1503.
5. Anderson, H. L., S. J. Martin and D. D. C. Bradley (1994) Synthesis and third-order nonlinear optical properties of a conjugated porphyrin polymer. Angew. Chem. Int. Ed. Engl. 33, 655-657.
6. Wagner, R. W., T. E. Johnson, F. Li and J. S. Lindsey (1995) Synthesis of ethyne-linked or butadiyne-linked porphyrin arrays using mild, copper-free, palladium-mediated coupling reactions. J. Org. Chem 60, 5266-5273.
7. Lin, V. S.-Y., S. G. DiMagno and M. J. Therien (1994) Highly conjugated, acetylene-bridged porphyrins: new models for light-harvesting antenna systems. Science 264, 1105-1111.
8. Anderson, H. L. and J. K. M. Sanders (1990) Amine-template-directed synthesis of cyclic porphyrin oligomers. Angew. Chem. Int. Ed. Engl. 29, 1400-1403.
9. Anderson, H. L. and J. K. M. Sanders (1992) Recognition of giant cluster anions by a protonated porphyrin trimer. J. Chem. Soc. Chem. Commun., pp. 946-947.
10. Mackay, L. G., H. L. Anderson and J. K. M. Sanders (1992) A platinum-linked porphyrin trimer. J. Chem. Soc. Chem. Commun., pp. 4344-4345.
11. Anderson, H. L. (1992) Meso-alkynyl porphyrins. Tetrahedron Lett. 33, 1101-1104.
12. Milgrom, L. R. and G. Yahioglu (1995) 5,10,15.20-Tetraarylethynylporphyrins. Tetrahedron Lett. 36, 9061-9064.
13. Milgrom, L. R. and G. Yahioglu (1996) Trans-disubstituted meso-tetraarylethynylporphyrins. Tetrahedron Lett. 37, 4069-4072.
14. Milgrom, L. R., G. Yahioglu, D. W. Bruce, S. Morrone, F. Z. Henari and W. J. Blau (1997) Mesogenic Zn(II) complexes of 5,10.15,20-tetraarylethynyl-substituted porphyrins. Adv. Mater. 9, 313-316.
15. Henari, F. Z., W. J. Blau, L. R. Milgrom, G. Yahioglu, D. Phillips and J. A. Lacey (1997) Third-order optical non-linearity in Zn(II) complexes of 5,10,15,20-tetraarylethynyl-substituted porphyrins. Chem. Phys Lett. 267, 229-233.
16. Bonnett, R. (1995) Photosensitisers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem. Soc. Rev., pp. 19-33.
17. Gouterman, M. (1978) In The Porphyrins, Vol. 3 (Edited by D. Dolphin), pp. 1-165 Academic Press, New York.
18. Buchler, J. W. (1978) In The Porphyrins, Vol. 1 (Edited by D. Dolphin), pp. 389-483. Academic Press, New York.
19. O'Connor, D. V. and D. Phillips (1984) Time Correlated Single Photon Counting. Academic Press, London.
20. Latimer, P., T. T. Bannister and E. Rabinowitch (1956) Quantum yields of fluorescence of plant pigments. Science 124, 585-586.
21. Seybold, P. G. and M. Gouterman (1969) Porphyrins III. Fluorescence spectra and quantum yields. J. Mol. Spectrosc. 31, 1-13.
22. Krasnovsky, A. A. (1979) Photoluminescence of singlet oxygen in pigment solutions. Photochem. Photobiol. 29, 29-36.
23. Wilkinson, F., W. P. Helman and A. B. Ross (1993) Quantum yields for the photosensitised formation of the lowest electronically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22, 113-263.
24. Dhami, S. (1996) Photophysics of phthalocyanines in the microheterogeneous systems. Ph.D. thesis, University of London.
25. Gouterman, M. (1961) Spectra of porphyrins J. Mol. Spectrosc. 6, 138-163.
26. Reynolds, C. H. (1988) An AM1 theoretical study of the structure and electronic properties of porphyrin. J. Org. Chem. 53, 6061-6064. (Interestingly, these calculations confirm the degeneracy imposed on the porphin HOMO and LUMO by the four-orbital theory, and are interpreted in terms of electron-pair correlation effects).
27. Rossbroich, G., N. A. Garcia and S. E. Braslavsky (1985) Thermal-lensing measurements of singlet oxygen: quantum yields of formation and lifetimes. J. Photochem. 31, 37-48.
28. Carmichael, I. and G. L. Hug (1986) Triplet-triplet absorption spectra of organic molecules in condensed phases. J. Phys. Chem. Ref. Data 15, 1.
29. Keir, W. F., E. J. Land, A. H. MacLennon, D. J. McGarvey and T. G. Truscott (1987) Pulsed radiation studies of photodynamic sensors: the nature of DHE. Photochem. Photobiol. 46, 587-589.
30. Pekkarinen, L. and H. Linschitz (1960) Studies on metastable states of porphyrins. J. Am. Chem. Soc. 82, 2407-2411.