Spectroscopic studies on the selective inclusion of amphiphilised porphyrin derivatives in micellar phases

Journal of Porphyrins and Phthalocyanines

Volumn 7, Issue 3, 2003, Pages 181-190

  Monti, Donato ^a   Pastorini, Alessandra ^a   Venanzi, Mariano ^a   Borocci, Stefano ^b   Mancini, Giovanna ^b  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Biomimetic chemistry; Fluorescence spectroscopy; Micelles; Porphyrinoids

Indexed keywords

2 [2 [2 [4 (10,15,20 TRIPHENYL 5 PORPHYRINYL)PHENOXY]ETHOXY]ETHOXY]ETHANOL; ALKENE; AMPHOPHILE; CYTOCHROME P450; FUNCTIONAL GROUP; MACROCYCLIC COMPOUND; MANGANESE DERIVATIVE; POLIDOCANOL; PORPHYRIN DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG; [5 [4 (3 TRIMETHYLAMMONIUM)PROPYLOXYPHENYL] 10,15,20 TRIPHENYLPORPHYRIN]CHLORIDE;

ARTICLE; BINDING AFFINITY; BIOMIMETICS; CATALYSIS; EPOXIDATION; FLUORESCENCE SPECTROSCOPY; MICELLE; MOLECULAR PROBE; SPECTROSCOPY;

EID: 0038170533     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424603000252     Document Type: Article

References (79)

1. a) Meunier B, Robert A, Pratviel G and Bernadou J. In The Porphyrin Handbook, Vol. 4, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 119-187.
2. b) Suslick KS. In The Porphyrin Handbook, Vol. 4, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 41-63.
3. c) Sheldon RA. In Metalloporphyrins in Catalytic Oxidation, Sheldon RA. (Ed.) Dekker, M.: New York, 1994; pp 1-27.
4. Ortiz de Montellano PR. Cytochrome P-450: Structure, Mechanism, and Biochemistry; 2nd ed.; Kluwer Academic Publishers, 1995; p 664.
5. a) Groves JT and Neumann R. J. Am. Chem. Soc. 1987; 109: 5045-5047.
6. b) Groves JT and Neumann R. J. Am. Chem. Soc. 1989; 111: 2900-2909.
7. c) Groves JT, Fate GD and Lahiri J. J. Am. Chem. Soc. 1994; 116: 5477-5478.
8. d) Schenning APHJ, Spelberg JHL, Hubert DHW, Feiters MC and Molte RJM. Chem.-Eur. J. 1998; 4: 871-880.
9. e) Schenning APHJ, Hubert DHW, van Esch JH, Feiters MC and Nolte RJM. Angew. Chem., Int. Ed. 1994; 33: 2468-2470.
10. f) van Esch J, Roks MFM and Nolte RJM. J. Am. Chem. Soc. 1986; 108: 6093-6094.
11. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
12. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
13. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
14. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
15. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
16. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
17. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
18. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
19. The use of an organised medium like liposomes, vesicles, monolayers, and micelles may have a strong effect on the features of a given reaction. For some selected references see: a) Bunton CA and Savelli G. Adv. Phys. Org. Chem. 1986; 22: 213-309. b) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. c) Cerichelli G, Luchetti L and Mancini G. Tetrahedron 1996; 52: 2465-2470. d) Scrimin P, Tecilla P and Tonellato U. J. Org. Chem. 1994; 59: 4194-4201. e) Cerichelli G, Mancini G and Luchetti L. Tetrahedron 1994; 50: 3797-3802. f) Grassert I, Paetzold E and Oehme G. Tetrahedron 1993; 49: 6605-6612. g) Cerichelli G, Coreno M and Mancini G. J. Colloid Interface Sci. 1993; 158: 33-39. h) Buriak JM and Osborn JA. Organometallics 1996; 15: 3161-3169. i) Grassert I, Schinkowski K, Vollhardt D and Oehme G. Chirality 1998; 10: 754-759.
20. For some selected references on the chemistry of amphiphile aggregates as synthetic membrane systems see: a) Fuhrhop J-H, Köning J and Stoddart JF, Eds. Membranes and Molecular Assemblies: The Synkinetic Approach; Springer-Verlag Inc.: New York, 1997. b) Menger FM and Gabrielson KD. Angew. Chem., Int. Ed. 1995; 34: 2091-2106. c) Menger FM and Angelova MI. Acc. Chem. Res. 1998; 31: 789-797. d) Ringsdorf H, Schlarb B and Venzmer J. Angew. Chem. 1998; 100: 117-162. e) Carmona-Ribeiro AM. Chem. Soc. Rev. 1992; 21: 209-214.
21. For some selected references on the chemistry of amphiphile aggregates as synthetic membrane systems see: a) Fuhrhop J-H, Köning J and Stoddart JF, Eds. Membranes and Molecular Assemblies: The Synkinetic Approach; Springer-Verlag Inc.: New York, 1997. b) Menger FM and Gabrielson KD. Angew. Chem., Int. Ed. 1995; 34: 2091-2106. c) Menger FM and Angelova MI. Acc. Chem. Res. 1998; 31: 789-797. d) Ringsdorf H, Schlarb B and Venzmer J. Angew. Chem. 1998; 100: 117-162. e) Carmona-Ribeiro AM. Chem. Soc. Rev. 1992; 21: 209-214.
22. For some selected references on the chemistry of amphiphile aggregates as synthetic membrane systems see: a) Fuhrhop J-H, Köning J and Stoddart JF, Eds. Membranes and Molecular Assemblies: The Synkinetic Approach; Springer-Verlag Inc.: New York, 1997. b) Menger FM and Gabrielson KD. Angew. Chem., Int. Ed. 1995; 34: 2091-2106. c) Menger FM and Angelova MI. Acc. Chem. Res. 1998; 31: 789-797. d) Ringsdorf H, Schlarb B and Venzmer J. Angew. Chem. 1998; 100: 117-162. e) Carmona-Ribeiro AM. Chem. Soc. Rev. 1992; 21: 209-214.
23. For some selected references on the chemistry of amphiphile aggregates as synthetic membrane systems see: a) Fuhrhop J-H, Köning J and Stoddart JF, Eds. Membranes and Molecular Assemblies: The Synkinetic Approach; Springer-Verlag Inc.: New York, 1997. b) Menger FM and Gabrielson KD. Angew. Chem., Int. Ed. 1995; 34: 2091-2106. c) Menger FM and Angelova MI. Acc. Chem. Res. 1998; 31: 789-797. d) Ringsdorf H, Schlarb B and Venzmer J. Angew. Chem. 1998; 100: 117-162. e) Carmona-Ribeiro AM. Chem. Soc. Rev. 1992; 21: 209-214.
24. For some selected references on the chemistry of amphiphile aggregates as synthetic membrane systems see: a) Fuhrhop J-H, Köning J and Stoddart JF, Eds. Membranes and Molecular Assemblies: The Synkinetic Approach; Springer-Verlag Inc.: New York, 1997. b) Menger FM and Gabrielson KD. Angew. Chem., Int. Ed. 1995; 34: 2091-2106. c) Menger FM and Angelova MI. Acc. Chem. Res. 1998; 31: 789-797. d) Ringsdorf H, Schlarb B and Venzmer J. Angew. Chem. 1998; 100: 117-162. e) Carmona-Ribeiro AM. Chem. Soc. Rev. 1992; 21: 209-214.
25. a) Monti D, Tagliatesta P, Mancini G and Boschi T. Angew. Chem., Int. Ed. 1998; 37: 1131-1133.
26. b) Borocci S, Marotti F, Mancini G, Monti D and Pastorini A. Langmuir 2001; 17: 7198-7203.
27. c) Monti D, Pastorini A, Mancini G, Borocci S and Tagliatesta P. J. Mol. Catal. A: Chem. 2002; 179: 125-131.
28. For some examples of aggregation of porphyrin derivatives in aqueous solutions see: a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio Venturo G and Hinds LC. J. Am. Chem. Soc. 1972; 94: 4511-4517. b) Guilard R, Senglet N, Liu YH, Sazou D, Findsen E, Faure D, Des Courieres T and Kadish KM. Inorg. Chem. 1991; 30: 1898-1905. c) Schenning APHJ, Feiters MC and Nolte RJM. Tetrahedron Lett. 1993; 34: 7077-7080. d) Kano K, Minamizono H, Kitae T and Negi S. J. Phys. Chem. A 1997; 101: 6118-6124. e) Schell C and Hombrecher HK. Chem. - Eur. J. 1999; 5: 587-598.
29. For some examples of aggregation of porphyrin derivatives in aqueous solutions see: a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio Venturo G and Hinds LC. J. Am. Chem. Soc. 1972; 94: 4511-4517. b) Guilard R, Senglet N, Liu YH, Sazou D, Findsen E, Faure D, Des Courieres T and Kadish KM. Inorg. Chem. 1991; 30: 1898-1905. c) Schenning APHJ, Feiters MC and Nolte RJM. Tetrahedron Lett. 1993; 34: 7077-7080. d) Kano K, Minamizono H, Kitae T and Negi S. J. Phys. Chem. A 1997; 101: 6118-6124. e) Schell C and Hombrecher HK. Chem. - Eur. J. 1999; 5: 587-598.
30. For some examples of aggregation of porphyrin derivatives in aqueous solutions see: a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio Venturo G and Hinds LC. J. Am. Chem. Soc. 1972; 94: 4511-4517. b) Guilard R, Senglet N, Liu YH, Sazou D, Findsen E, Faure D, Des Courieres T and Kadish KM. Inorg. Chem. 1991; 30: 1898-1905. c) Schenning APHJ, Feiters MC and Nolte RJM. Tetrahedron Lett. 1993; 34: 7077-7080. d) Kano K, Minamizono H, Kitae T and Negi S. J. Phys. Chem. A 1997; 101: 6118-6124. e) Schell C and Hombrecher HK. Chem. - Eur. J. 1999; 5: 587-598.
31. For some examples of aggregation of porphyrin derivatives in aqueous solutions see: a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio Venturo G and Hinds LC. J. Am. Chem. Soc. 1972; 94: 4511-4517. b) Guilard R, Senglet N, Liu YH, Sazou D, Findsen E, Faure D, Des Courieres T and Kadish KM. Inorg. Chem. 1991; 30: 1898-1905. c) Schenning APHJ, Feiters MC and Nolte RJM. Tetrahedron Lett. 1993; 34: 7077-7080. d) Kano K, Minamizono H, Kitae T and Negi S. J. Phys. Chem. A 1997; 101: 6118-6124. e) Schell C and Hombrecher HK. Chem. - Eur. J. 1999; 5: 587-598.
32. For some examples of aggregation of porphyrin derivatives in aqueous solutions see: a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio Venturo G and Hinds LC. J. Am. Chem. Soc. 1972; 94: 4511-4517. b) Guilard R, Senglet N, Liu YH, Sazou D, Findsen E, Faure D, Des Courieres T and Kadish KM. Inorg. Chem. 1991; 30: 1898-1905. c) Schenning APHJ, Feiters MC and Nolte RJM. Tetrahedron Lett. 1993; 34: 7077-7080. d) Kano K, Minamizono H, Kitae T and Negi S. J. Phys. Chem. A 1997; 101: 6118-6124. e) Schell C and Hombrecher HK. Chem. - Eur. J. 1999; 5: 587-598.
33. For some recent spectroscopic studies on interacting porphyrin chromophores see: a) Ribo JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc., Chem. Commun. 1994: 681-682. b) Ribo JM, Bofill JM, Crusats J and Rubires R. Chem. - Eur. J. 2001; 7: 2733-2737.
34. For some recent spectroscopic studies on interacting porphyrin chromophores see: a) Ribo JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc., Chem. Commun. 1994: 681-682. b) Ribo JM, Bofill JM, Crusats J and Rubires R. Chem. - Eur. J. 2001; 7: 2733-2737.
35. Gouterman M. In The Porphyrins, Vol. III, Dolphin D. (Ed.) Academic: New York, 1978; pp 1-165.
36. a) Ramachandran C, Pyter RA and Mukerjee P. J. Phys. Chem. 1982; 86: 3198-3205.
37. b) Romsted LS. In Surfactants in Solution, Vol. 2, Mittal KL. (Ed.) Perseus Publishing, 1984; p 105.
38. -4 M with no trace of precipitate detected. Moreover, the absence of a broad band at 450 nm, typical of porphyrin aggregates in water, indicates a complete inclusion of the chromophores in micellar phase. The small fraction of the added organic solvents does not alter the microscopic features of the micelle to a detectable extent. This is a safe assumption, as the percentage of organic solvent in the final solution did not exceed the value of 0.5%.
39. a) Schenning APHJ, Hubert DHW, Feiters MC and Nolte RJM. Langmuir 1996; 12: 1572-1577.
40. b) van Esch JH, Feiters MC, Peters AM and Nolte RJM. J. Phys. Chem. 1994; 98: 5541-5551.
41. Blatt E and Sawyer WH. Biochim. Biophys. Acta 1985; 822: 43-62.
42. a) Critical micelle concentration (cmc) of CTAB and Brij 35 are 0.8 and 0.05 mM respectively: Fendler JH and Fendler EJ. Catalysis in Micellar and Macromolecular Systems; Academic Press, Inc.: New York, 1975.
43. b) The cmc of CTAN is 0.8 mM, Lissi EA, Abuin EB, Sepulveda L and Quina FH. J. Phys. Chem. 1984; 88: 81-85.
44. Cerichelli G, Grande C, Luchetti L, Mancini G and Bunton CA. J. Org. Chem. 1987; 52: 5167-5171.
45. Monti D, Venanzi M, Cantonetti V, Borocci S and Mancini G. Chem. Commun. (Cambridge, U. K.) 2002: 774-775.
46. The quenching efficiency of bromide is very low (γ = 0.04), see for example: Dewey TG. Biophysical and biochemical aspects of fluorescence spectroscopy; Kluwer Academic: New York, 1990; p 312.
47. Fuhrhop JH and Mathieu J. Angew. Chem. 1984; 96: 124-137.
48. For a general discussion on this topic see Vermathen: M, Louie EA, Chodosh AB, Ried S and Simonis U. Langmuir 2000; 16: 210-221.
49. a) Magid LJ, Han Z, Warr GG, Cassidy MA, Butler PD and Hamilton WA. J. Phys. Chem. B 1997; 101: 7919-7927.
50. b) Ranganathan R, Tran L and Bales BL. J. Phys. Chem. B 2000; 104: 2260-2264.
51. c) Imae T, Abe A and Ikeda S. J. Phys. Chem. 1988; 92: 1548-1553.
52. d) Gehlen MH and De Schryver FC. Chem. Rev. (Washington, DC, U. S.) 1993; 93: 199-221.
53. e) Mancini G, Schiavo C and Cerichelli G. Langmuir 1996; 12: 3567-3573.
54. It is known, in fact, that the increase of the ionic strength of the medium may promote the aggregation of water soluble porphyrin derivatives. See for example: a) Ribo JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc., Chem. Commun. 1994: 681-682. b) Pasternack RF, Schaefer KF and Hambright P. Inorg. Chem. 1994; 33: 2062-2065. c) Sutter TPG, Rahmatollah RP, Hambright P, Bommer JC, Manmohan K and Pedatsur N. J. Chem. Soc. Faraday Trans. 1993; 89: 495-502.
55. It is known, in fact, that the increase of the ionic strength of the medium may promote the aggregation of water soluble porphyrin derivatives. See for example: a) Ribo JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc., Chem. Commun. 1994: 681-682. b) Pasternack RF, Schaefer KF and Hambright P. Inorg. Chem. 1994; 33: 2062-2065. c) Sutter TPG, Rahmatollah RP, Hambright P, Bommer JC, Manmohan K and Pedatsur N. J. Chem. Soc. Faraday Trans. 1993; 89: 495-502.
56. It is known, in fact, that the increase of the ionic strength of the medium may promote the aggregation of water soluble porphyrin derivatives. See for example: a) Ribo JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc., Chem. Commun. 1994: 681-682. b) Pasternack RF, Schaefer KF and Hambright P. Inorg. Chem. 1994; 33: 2062-2065. c) Sutter TPG, Rahmatollah RP, Hambright P, Bommer JC, Manmohan K and Pedatsur N. J. Chem. Soc. Faraday Trans. 1993; 89: 495-502.
57. Cerichelli G and Mancini G. Langmuir 2000; 16: 182-187. Interestingly, the critical micelle concentration of CTAX is not influenced by the presence of the porphyrin solute, within the investigated concentration range.
58. -. See for example: a) Meguro K, Ueno M and Esumi K. In Nonionic Surfactants: Physical Chemistry, 2nd ed., Vol. 23, Schick MJ. (Ed.) Dekker Marcel Incorporated: New York, 1987; p 1158. b) Kumar S, Sharma D, Khan ZA and Kabir ud D. Langmuir 2002; 18: 4205-4209.
59. -. See for example: a) Meguro K, Ueno M and Esumi K. In Nonionic Surfactants: Physical Chemistry, 2nd ed., Vol. 23, Schick MJ. (Ed.) Dekker Marcel Incorporated: New York, 1987; p 1158. b) Kumar S, Sharma D, Khan ZA and Kabir ud D. Langmuir 2002; 18: 4205-4209.
60. a) Maiti NC, Mazumdar S and Periasamy N. J. Phys. Chem. 1995; 99: 10708-10715.
61. b) Pispisa B, Stella L, Venanzi M, Palleschi A, Viappiani C, Polese A, Formaggio F and Toniolo C. Macromolecules 2000; 33: 906-915.
62. Khairutdinov RF and Serpone N. J. Phys. Chem. 1995; 99: 11952-11958.
63. a) Regev A, Michaeli S, Levanon H, Cyr M and Sessler JL. J. Phys. Chem. 1991; 95: 9121-9129.
64. b) Roitman L, Ehrenberg B, Nitzan Y, Kral V and Sessler JL. Photochem. Photobiol. 1994; 60: 421-426.
65. c) For photophysical studies on fluorescent, covalently linked, dimeric porphyrins see: Chow YFA, Dolphin D, Paine JP, III, McGarvey D, Pottier R and Truscott TG. J. Photochem. Photobiol., B 1988; 2: 253-263.
66. Steiner RF. In Topics in Fluorescence Spectroscopy, Vol. 2, Lakowicz JR. (Ed.) Kluwer Academic Publishers: New York, 1991.
67. Stubbs CD and Williams BW. In Topics in Fluorescence Spectroscopy, Vol. 3, Lakowicz JR. (Ed.) Kluwer Academic Publishers: New York, 1992.
68. Borbely S. Langmuir 2000; 16: 5540-5545.
69. For some selected references see: a) Ali H and Van Lier JE. Chem. Rev. (Washington, DC, U. S.) 1999; 99: 2379-2450. b) Bonnett R. Chem. Soc. Rev. 1995; 24: 19-33. c) Ricchelli F. J. Photochem. Photobiol., B 1995; 29: 109-118. d) Pandey RK and Zheng G. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 157-230.
70. For some selected references see: a) Ali H and Van Lier JE. Chem. Rev. (Washington, DC, U. S.) 1999; 99: 2379-2450. b) Bonnett R. Chem. Soc. Rev. 1995; 24: 19-33. c) Ricchelli F. J. Photochem. Photobiol., B 1995; 29: 109-118. d) Pandey RK and Zheng G. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 157-230.
71. For some selected references see: a) Ali H and Van Lier JE. Chem. Rev. (Washington, DC, U. S.) 1999; 99: 2379-2450. b) Bonnett R. Chem. Soc. Rev. 1995; 24: 19-33. c) Ricchelli F. J. Photochem. Photobiol., B 1995; 29: 109-118. d) Pandey RK and Zheng G. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 157-230.
72. For some selected references see: a) Ali H and Van Lier JE. Chem. Rev. (Washington, DC, U. S.) 1999; 99: 2379-2450. b) Bonnett R. Chem. Soc. Rev. 1995; 24: 19-33. c) Ricchelli F. J. Photochem. Photobiol., B 1995; 29: 109-118. d) Pandey RK and Zheng G. In The Porphyrin Handbook, Vol. 6, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: San Diego, 2000; pp 157-230.
73. a) Moan J and Sommer S. Photochem. Photobiol. 1984; 40: 631-634.
74. b) Blum A and Grossweiner LI. Photochem. Photobiol. 1985; 41: 27-32.
75. c) Aveline BM, Hasan T and Redmond RW. J. Photochem. Photobiol., B 1995; 30: 161-169.
76. d) Smith GJ. Photochem. Photobiol. 1985; 41: 123-126.
77. e) Hoebeke M. J. Photochem. Photobiol., B 1995; 28: 189-196.
78. Perrin DD, Armarego WLF and Perrin DE. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: New York, 1980.
79. Duynstee EFJ and Grunwald E. J. Am. Chem. Soc. 1959; 81: 4540-4542.