Abstract
In neutral and alkaline solutions, tetrakis(4-carboxyphenyl)porphyrin (TCPP) and tetrakis(4-sulfonatophenyl)porphyrin (TSPP) form 1:1 and 2:1 host–guest inclusion complexes with α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), and 6-deoxy-6-diethylamino-β-CD (DEA-β-CD), except for DEA-β-CD in alkaline solution. On the other hand, TCPP and TSPP form only 1:1 inclusion complexes with 6-deoxy-6-dihexylamino-β-CD (DHA-β-CD). The limited solubilities of DEA-β-CD in alkaline solution and DHA-β-CD are likely responsible for no observation of the 2:1 inclusion complex containing DEA-β-CD in alkaline solution and that containing DHA-β-CD. The equilibrium constants (Ks) of TCPP and TSPP for the formation of the inclusion complexes have been estimated from the absorption and/or fluorescence intensity changes in neutral and alkaline solutions. The K2 values, which are the equilibrium constants for the formation of the 2:1 host–guest inclusion complex from the 1:1 inclusion complex, are about one tenth the corresponding K1 values, except for the α-CD–TSPP system in alkaline solution. In neutral solution, where DEA-β-CD and DHA-β-CD are in protonated forms, the electrostatic force operates between DEA-β-CD (DHA-β-CD) and TCPP (TSPP), leading to the greater K values than those in alkaline solution, where DEA-β-CD and DHA-β-CD exist as neutral species.
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References
W. Saenger (1980) Angew. Chem. Int. Ed. Engl 19 344
H. Hirai, N. Toshima, S. Hayashi, and Y. Fujii: Chem. Lett. 643 (1983).
J.S. Manka D.S. Lawrence (1989) Tetrahedron Lett 30 7341
J.S. Manka D.S. Lawrence (1990) J. Am. Chem. Soc 112 2440
S. Mosseri J.C. Mialocq B. Perly P. Hambright (1991) J. Phys. Chem 95 2196
S. Mosseri J.C. Mialocq B. Perly P. Hambright (1991) J. Phys. Chem 95 4659
J.M. Ribo J. Farrera M.L. Valero A. Virgili (1995) Tetrahedron 51 3705
K. Kano, N. Tanaka, H. Minamizono, and Y. Kawakita: Chem. Lett. 925 (1996).
K. Kano R. Nishiyabu T. Asada Y. Kuroda (2002) J. Am. Chem. Soc 124 9937
T. Carofiglio R. Fornasier V. Lucchini C. Rosso U. Tonellato (1996) Tetrahedron Lett 37 8019
S. Hamai T. Koshiyama (1999) J. Photochem. Photobiol. A: Chem 127 135
S. Hamai T. Koshiyama (2001) Spectrochim. Acta A 57 985
S. Hamai H. Satou (2001) Spectrochim. Acta A 57 1745
S. Hamai (2002) Bull. Chem. Soc. Jpn 75 2371
S. Tamagaki, K. Fukuda, H. Maeda, N. Mimura, and W. Tagaki: J. Chem. Soc., Perkin Trans. 2 389, (1995).
N. Ito, N. Yoshida, and K. Ichikawa: J. Chem. Soc., Perkin Trans. 2 965 (1996).
K. Kano, T. Kitae, H. Takashima, and Y. Shimofuri: Chem. Lett. 899 (1997).
T. Kitae, T. Nakayama, and K. Kano: J. Chem. Soc., Perkin Trans. 2 207 (1998).
S. Hamai S. Ishikawa (2001) Spectrochim. Acta A 57 1
N.C. Maiti S. Mazumdar N. Periasamy (1998) J. Phys. Chem. B 102 1528
H.A. Benesi J.H. Hildebrand (1949) J. Am. Chem. Soc 71 2703
S. Hamai (1982) Bull. Chem. Soc. Jpn 55 2721
J.R. Lakowicz (1999) Principles of Fluorescence Spectroscopy EditionNumber2 Kluwer Academic/Plenum Publishers New York
J.M. Ribo, J. Crusats, J. Farrera, and M.L. Valero: J. Chem. Soc., Chem. Commun. 681 (1994).
J. Mosinger M. Deumie K. Lang P. Kubat D.M. Wagnerova (2000) J. Photochem. Photobiol. A: Chem 130 13
J. Itoh T. Yotsuyanagi K. Aomura (1975) Anal. Chim. Acta 74 53
B.G. Anex R.S. Umans (1964) J. Am. Chem. Soc 86 5026
S. Matile N. Berova K. Nakanishi J. Fleischhauer R.W. Woody (1996) J. Am. Chem. Soc 118 5198
M. Kodaka T. Fukaya (1989) Bull. Chem. Soc. Jpn 62 1154
N. Kobayashi T. Osa (1991) Bull. Chem. Soc. Jpn 64 1878
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Hamai, S., Ohshida, T. Inclusion Complexes of Cyclodextrins with Tetrakis(4-carboxyphenyl)porphyrin and Tetrakis(4-sulfonatophenyl)porphyrin in Aqueous Solutions. J Incl Phenom Macrocycl Chem 50, 209–217 (2004). https://doi.org/10.1007/s10847-004-9650-5
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DOI: https://doi.org/10.1007/s10847-004-9650-5