Synthesis and luminescence of soluble meso-unsubstituted tetrabenzo- and tetranaphtho[2,3]porphyrins

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9562-9572

  Finikova, Olga S ^a   Cheprakov, Andrei V ^b   Vinogradov, Sergei A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ANNEALING; AROMATIZATION; PHOSPHORESCENCE; PHOSPHORS; QUANTUM THEORY; SYNTHESIS (CHEMICAL);

ABSORPTION BANDS; SUBSTITUENTS; TETRABENZOPORPHYRINS (TBP);

PORPHYRINS;

AROMATIC COMPOUND; BENZOPORPHYRIN DERIVATIVE; METAL COMPLEX; PORPHYRIN DERIVATIVE; TETRANAPHTHO[2,3]PORPHYRIN; UNCLASSIFIED DRUG; ZINC COMPLEX;

AROMATIZATION; ARTICLE; COMPLEX FORMATION; LUMINESCENCE; NEAR INFRARED SPECTROSCOPY; PHOSPHORESCENCE; QUANTUM CHEMISTRY; SCANNING TUNNELING MICROSCOPY; SOLUBILIZATION; SYNTHESIS;

LUMINESCENCE; METALLOPORPHYRINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PORPHYRINS; SOLUBILITY; ZINC;

EID: 27744523700     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051580r     Document Type: Article

References (142)

1. (a) Lash, T. D. In The Porphyrin Handbook, Kadish, K. M.; Smith, K. M.; Guilard, R. Eds.; Academic Press: New York; 2000, Chapter 10.
2. (b) Lash, T. D. J. Porphyrins Phthalocyanines 2001, 5, 267.
3. (c) Vicente, M. G. H.; Smith, K. M. J. Porphyrins Phthalocyanines 2004, 8, 26.
4. (a) Bonnett, R. Chem. Soc. Rev. 1995, 24, 19.
5. (b) Sessler, J. L.; Dow, W. C.; Oconnor, D.; Harriman, A.; Hemmi, G.; Mody, T. D.; Miller, R. A.; Qing, F.; Springs, S.; Woodburn, K.; Young, S. W. J. Alloys Compd. 1997, 249, 146.
6. (c) Pandey, R. K. In ref 1a, Chapter 43.
7. (d) Brunner, H.; Scheuerer, K. M. Monatsh. Chem. 2002, 133, 679.
8. (e) Moan, J.; Peng, Q. Anticancer Res. 2003, 23, 3591.
9. (f) Nyman, E. S.; Hynninen, P. H. J. Photochem. Photobiol, B 2004, 73, 1.
10. (a) Young, S. W.; Qing, F.; Harriman, A.; Sessler, J. L.; Dow, W. C.; Mody, T. D.; Hemmi, G. W.; Hao, Y. P.; Miller, R. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 6610.
11. (b) Vinogradov, S. A.; Lo, L.-W.; Jenkins, W. T.; Evans, S. M.; Koch, C.; Wilson, D. F. Biophys. J. 1996, 70, 1609.
12. (c) Liebsch, G.; Klimant, I.; Frank, B.; Holst, G.; Wolfbeis, O. S. Appl. Spectrosc. 2000, 54, 548.
13. (d) Minamitani, H.; Tsukada, K.; Sekizuka, E.; Oshio, C. J. Pharm. Sci. 2003, 93, 227.
14. (e) Kress, M.; Meier, T.; Steiner, R.; Dolp, F.; Erdmann, R.; Ortmann, U.; Ruck, A. J. Biomed. Opt. 2003, 8, 26.
15. (f) Licha, K. Contrast Agents II 2002, 222, 1.
16. (a) Lavi, A.; Johnson, F. M.; Ehrenberg, B. Chem. Phys. Lett. 1994, 231, 144.
17. (b) Friedberg, J. S.; Skema, C.; Baum, E. D.; Burdick, J.; Vinogradov, S. A.; Wilson, D. F.; Horan, A. D.; Nachamkin, I. J. Antimicrob. Chemother. 2001, 48, 105.
18. Finikova, O. S.; Galkin, A. S.; Rozhkov, V. V.; Cordero, M. C.; Hagerhall, C.; Vinogradov, S. A. J. Am. Chem. Soc. 2003, 125, 4882.
19. (a) Chen, P. L.; Tomov, I. V.; Dvornikov, A. S.; Nakashima, M.; Roach, J. F.; Alabran, D. M.; Rentzepis, P. M. J. Phys. Chem. 1996, 100, 17507.
20. (b) Brunel, M.; Chaput, F.; Vinogradov, S. A.; Campagne, B.; Canva, M.; Boilot, J. P. Chem. Phys. 1997, 218, 301.
21. (c) Ono, N.; Ito, S.; Wu, C. H.; Chen, C. H.; Wen, T. C. Chem. Phys. 2000, 262, 467.
22. (d) Rogers, J. E.; Nguyen, K. A.; Hufnagle, D. C.; McLean, D. G.; Su, W. J.; Gossett, K. M.; Burke, A. R.; Vinogradov, S. A.; Pachter, R.; Fleitz, P. A. J. Phys. Chem. A 2003, 107, 11331.
23. (a) Perry, J. W.; Mansour, K.; Lee, I. S.; Wu, X.; Bedworth, P. V.; Chen, C. T.; Ng, D.; Marder, S. R.; Miles, P.; Wada, T.; Tian, M.; Sasabe, H. Science 1996, 273, 1533.
24. (b) Krivokapic, A.; Anderson, H. L.; Bourhill, G.; Ives, R.; Clark, S.; McEwan, K. J. Adv. Mater. 2001, 13, 652.
25. (c) Srinivas, N.; Rao, S. V.; Rao, D.; Kimball, B. K.; Nakashima, M.; Decristofano, B. S.; Rao, D. N. J. Porphyrins Phthalocyanines 2001, 5, 549.
26. (d) Dini, D.; Barthel, M.; Schneider, T.; Ottmar, M.; Verma, S.; Hanack, M. Solid State Ionics 2003, 165, 289.
27. (e) Calvete, M.; Yang, G. Y.; Hanack, M. Synth. Met. 2004, 141, 231.
28. (a) Martinsen, J.; Pace, L. J.; Phillips, T. E.; Hoffman, B. M.; Ibers, J. A. J. Am. Chem. Soc. 1982, 104, 83.
29. (b) Martinsen, J.; Pace, L. J.; Phillips, T. E.; Hoffman, B. M.; Ibers, J. A. J. Am. Chem. Soc. 1982, 104, 83.
30. (c) Liou, K. Y.; Newcomb, T. P.; Heagy, M. D.; Thompson, J. A.; Heuer, W. B.; Musselman, R. L.; Jacobsen, C. S.; Hoffman, B. M.; Ibers, J. A. Inorg. Chem. 1992, 31, 4517.
31. (d) Aramaki, S.; Sakai, Y.; Ono, N. Appl. Phys. Lett. 2004, 84, 2085.
32. (a) Yamashita, K. Chem. Lett. 1982, 1085.
33. (b) Yamashita, K.; Harima, Y.; Kubota, H.; Suzuki, H. Bull. Chem. Soc. Jpn. 1987, 60, 803.
34. Guo, X. L.; Dong, Z. C.; Trifonov, A. S.; Miki, K.; Mashiko, S.; Okamoto, T. Nanotechnology 2004, 15, S402.
35. (a) Vanderkooi, J. M.; Maniara, G.; Green, T. J.; Wilson, D. F. J. Biol. Chem. 1987, 262, 5476.
36. (b) Rumsey, W. L.; Vanderkooi, J. M.; Wilson, D. F. Science 1988, 241, 1649.
37. (c) Wilson, D. F.; Vinogradov, S. A. In Handbook of Biomedical Fluorescence; Mycek, M.-A., Pogue, B. W., Eds.; Marcel Dekker: New York, 2003; Chapter 17.
38. (a) Eastwood, D.; Gouterman, M. J. Mol. Spectrosc. 1970, 35, 359.
39. (b) Callis, J. B.; Gouterman, M.; Jones, Y. M.; Henderson, B. H. J. Mol. Spectrosc. 1971, 39, 410.
40. (c) Callis, J. B.; Knowles, J. M.; Gouterman, M. J. Phys. Chem. 1973, 77, 154.
41. (d) Kim, D. H.; Holten, D.; Gouterman, M.; Buchler, J. W. J. Am. Chem. Soc. 1984, 106, 4015.
42. (a) Soloviev, V. Y.; Wilson, D. F.; Vinogradov, S. A. Appl. Opt. 2003, 42, 113.
43. (b) Soloviev, V. Y.; Wilson, D. F.; Vinogradov, S. A. Appl. Opt. 2004, 43, 564.
44. (a) Papkovsky, D. B.; Ponomarev, G. V.; Wolfbeis, O. S. Spectrochim. Acta A 1996, 52, 1629.
45. (b) Castellano, F. N.; Lakowicz, J. R. Photochem. Photobiol. 1998, 67, 179.
46. (c) Singh, A.; Johnson, L. W. Spectrochim. Acta A 2003, 59, 905.
47. (a) Vinogradov, S. A.; Wilson, D. F. J. Chem. Soc., Perkin Trans. 2 1995, 103.
48. (b) Vinogradov, S. A.; Wilson, D. F. Adv. Exp. Med. Biol. 1997, 411, 597.
49. (c) Rozhkov, V. V.; Khajehpour, M.; Vinogradov, S. A. Inorg. Chem. 2003, 42, 4253.
50. (a) Dunphy, I.; Vinogradov, S. A.; Wilson, D. F. Anal. Biochem. 2002, 310, 191.
51. (b) Rietveld, I. B.; Kim, E.; Vinogradov, S. A. Tetrahedron 2003, 59, 3821.
52. (c) Ziemer, L. S.; Lee, W. M. F.; Vinogradov, S. A.; Sehgal, C.; Wilson, D. F. J. Appl. Physiol. 2005, 98, 1503.
53. (d) Wilson, D. F.; Vinogradov, S. A.; Grosul, P.; Kuroki, A.; Bennett, J. Appl. Opt. 2005, 25, 5239.
54. (a) Dashkevich, S. N.; Kaliya, O. L.; Kopranenkov, V. N.; Luk'janets, E. A. Zh. Prikl. Spectrosk. (Russian) 1987, 47, 144.
55. (b) Sapunov, U. V.; Soloviev, K. N.; Kopranenkov, V. N.; Dashkevich, S. N. Teor. Exp. Khim. (Russian) 1991, 27, 105.
56. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51.
57. (d) Roitman, L.; Ehrenberg, B.; Kobayashi, N. J. Photochem. Photobiol., A 1994, 77, 23.
58. (a) Cheng, R. J.; Chen, Y. R.; Wang, S. L.; Cheng, C. Y. Polyhedron 1993, 12, 1353.
59. (b) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Dalosto, S.; Vinogradov, S. A. Inorg. Chem. 2002, 41, 6944.
60. See, for examples: Senge, M. O. In ref 1a, Chapter 6 and references therein.
61. See, for example: Haddad, R. E.; Gazeau, S.; Pecaut, J.; Marchon, J. C.; Medforth, C. J.; Shelnutt, J. A. J. Am. Chem. Soc. 2003, 125, 1253 and references therein.
62. (a) Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten, D. J. Am. Chem. Soc. 1994, 116, 7363-7368.
63. (b) Sazanovich, I. V.; Galievsky, V. A.; van Hoek, A.; Schaafsma, T. J.; Malinovskii, V. L.; Holten, D.; Chirvony, V. S. J. Phys. Chem. B 2001, 105, 7818.
64. (a) Nguyen, K. A.; Pachter, R. J. Chem. Phys. 2001, 114, 10757.
65. (b) Kobayashi, N.; Konami, H. J. Porphyrins Phthalocyanines 2001, 5, 233.
66. (c) Rosa, A.; Ricciardi, G.; Baerends, E. J.; van Gisbergen, S. J. A. J. Phys. Chem. A 2001, 105, 3311.
67. Wertsching, A. K.; Koch, A. S.; DiMagno, S. G. J. Am. Chem. Soc. 2001, 123, 3932.
68. Renner, M. W.; Cheng, R.-J.; Chang, C. K.; Fajer, J. J. Phys. Chem. 1990, 94, 8508.
69. (a) Cheng, R. J.; Chen, Y. R.; Chuang, C. E. Heterocycles 1992, 34, 1.
70. (b) Cheng, R. J.; Chen, Y. R.; Chen, C. C. Heterocycles 1994, 38, 1465.
71. (c) Cheng, R.-J.; Lin, S.-H.; Mo, H.-M. Organometallics 1997, 16, 2121.
72. (a) Helberger, J. H., von Rebay, A., and Hever, D. B. Just. Liebigs Ann. Chem. 1938, 533, 197.
73. (b) Helberger, J. H., Hever, D. B. Just. Liebigs Ann. Chem. 1938, 536, 173.
74. (a) Barrett, P. A.; Linstead, R. P.; Rundall, F. G.; Tuey, G. A. P. J. Chem. Soc. 1940, 1079.
75. (b) Linstead, R. P.; Weiss, F. T. J. Chem. Soc. 1950, 2975.
76. (a) Vogler, A.; Rethwisch, B.; Kunkely, H.; Hutterman, J.; Besenhard, J. O. Angew. Chem., Int. Ed. Engl. 1978, 17, 951.
77. (b) Vogler, A.; Kunkely, H.; Rethwisch, B. Inorg. Chim. Acta 1980, 46, 101.
78. (c) Fischer, K.; Hanack, M. Angew. Chem., Int. Ed. Engl. 1983, 22, 724.
79. (a) Kopranenkov, V. N.; Makarova, E. A.; Lukyanets, E. A. Russ. J. Gen. Chem. 1981, 51, 2727.
80. (b) Kopranenkov, V. N.; Makarova, E. A.; Dashkevich, S. N.; Luk'janets, E. A. Chem. Heterocycl. Compd. (Russian) 1988, 773.
81. (c) Vorotnikov, A. M.; Kopranenkov, V. N.; Lukyanets, E. A. Chem. Heterocycl. Compd. (Russian) 1994, 36.
82. (a) Edwards, L.; Gouterman, M.; Rose, C. B. J. Am. Chem. Soc. 1976, 98, 7638.
83. (b) Kopranenkov, V. N.; Tarkhanova, E. A.; Luk'yanets, E. A. Russ. J. Org. Chem. 1979, 15, 570.
84. (c) Koehorst, R. B. M.; Kleibeuker, J. F.; Tjeerd, J. S.; de Bie, D. A.; Geursten, B.; Henrie, R. N.; van der Plas, H. C. J. Chem. Soc. 1981, 1005.
85. (a) Bender, C. O.; Bonnett, R.; Smith, R. G. J. Chem. Soc. 1969, 345.
86. (b) Bender, C. O.; Bonnett, R.; Smith, R. G. J. Chem. Soc. 1970, 1251.
87. (c) Bender, C. O.; Bonnett, R.; Smith, R. G. J. Chem. Soc. 1972, 771.
88. (e) Matsuzawa, Y.; Ichimura, K.; Kudo, K. Inorg. Chim. Acta 1998, 277, 151.
89. Kopranenkov, V. N.; Makarova, Y. A.; Dashkevich, S. N.; Lukyanets, Y. A. Chem. Heterocycl. Compd. (Russian) 1982, 1563.
90. Kopranenkov, V. N.; Vorotnikov, A. M.; Lukyanets, E. A. Russ. J. Gen. Chem. 1979, 49, 2783.
91. (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Dashkevich, S. N.; Luk'yanets, E. A. J. Gen. Chem. (Russian) 1985, 803.
92. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601.
93. (a) Lash, T. Energy Fuels 1993, 7, 166.
94. (b) Lash, T. D.; Roper, T. J. Tetrahedron Lett. 1994, 35, 7715.
95. (c) Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533.
96. (d) Lash, T. D.; Denny, C. P. Tetrahedron 1995, 51, 59.
97. (e) Manley, J. M.; Roper, T. J.; Lash, T. D. J. Org. Chem. 2005, 70, 874.
98. Ono, N.; Hironaga, H.; Ono, K.; Kaneko, S.; Murashima, T.; Ueda, T.; Tsukamura, C.; Ogawa, T. J. Chem. Soc., Perkin. Trans. 1 1996, 417.
99. 4TBP from isoindole has been described, but it also required a condensation at high temperature: Remy, D. E. Tetrahedron Lett. 1983, 24, 1452.
100. Vicente, M. G. H.; Tome, A. C.; Walter, A.; Cavaleiro, J. A. S. Tetrahedron Lett. 1997, 38, 3639.
101. (a) Ito, S.; Murashima, T.; Uno, H.; Ono, N. Chem. Commun. 1998, 1661.
102. (b) Ito, S.; Ochi, N.; Murashima, T.; Uno, H.; Ono, N. Heterocycles 2000, 52, 399.
103. (c) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893.
104. (d) Ito, S.; Uno, H.; Murashima, T.; Ono, N. Tetrahedron Lett. 2001, 42, 45.
105. (e) Uno, H.; Ishikawa, T.; Hoshi, T.; Ono, N. Tetrahedron Lett. 2003, 44, 5163.
106. (f) Murashima, T.; Tsujimoto, S.; Yamada, T.; Miyazawa, T.; Uno, H.; Ono, N.; Sugimoto, N. Tetrahedron Lett. 2005, 46, 113.
107. (a) Finikova, O.; Cheprakov, A.; Beletskaya, I.; Vinogradov, S. Chem. Commun. 2001, 261.
108. (b) Finikova, O. S.; Cheprakov, A. V.; Beletskaya, I. P.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2004, 69, 522.
109. (a) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
110. (b) Finikova, O. S.; Aleshchenkov, S. E.; Brinas, R. P.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2005, 70, 4617.
111. The oxidation aromatization approach has been used before to synthesize aromatically π-extended porphyrins (for examples, see ref 35), but it has never been applied to the synthesis of meso-unsubstituted TBPs and TNPs.
112. Sessler, J. L.; Mozaffari, A.; Johnson, M, R. In Organic Synthesis; Freeman, J. P., Ed.; Wiley & Sons: New York, 1998; Vol. 70, p 68.
113. Oxidation states and spin states of FeTBP complexes depend strongly on the nature of their axial ligation. For examples, see: Kobayashi, N.; Koshiyama, M.; Osa, T. Inorg. Chem. 1985, 24, 2502 and ref 28a,b.
114. Rama Rao, A. V.; Yadav, J. S.; Bal Reddy, K.; Mehendale, A. R. Tetrahedron 1984, 40, 4643.
115. Lash, T. D.; Bellettini, J. R.; Bastian, J. A.; Couch, K. B. Synthesis 1994, 170.
116. 41b
117. (a) Savoia, D.; Trombini, C.; Umani-Ronci, A. J. Chem. Soc., Perkin Trans. 1 1977, 123.
118. (b) Inomata, K.; Hirata, T.; Kinoshita, H.; Kotake, H.; Senda, H. Chem. Lett. 1988, 2009.
119. (a) Barton, D.; Zard, S. J. Chem. Soc., Chem. Commun. 1985, 1098.
120. (b) Barton, D.; Kervagoret, J.; Zard, S. Tetrahedron 1990, 46, 7587.
121. (c) Arnold, D. P.; Burgess-Dean, L.; Hubbard, J.; Abdur Rahman, M. Aust. J. Chem. 1994, 47, 969.
122. (d) Abel, Y.; Haake, E.; Haake, G.; Schmidt, W.; Struve, D.; Walter, A.; Montforts, F. P. Helv. Chim. Acta 1998, 81, 1978.
123. For example see: (a) Sevchenko, A. N.; Soloviev, K. N.; Shkirman, S. F.; Kachura, T. F. Proc. Natl. Acad. Sci. USSR (Russian) 1965, 161, 1313.
124. (b) Sevchenko, A. N.; Soloviev, K. N.; Gradushko, A. T.; Shkirman, S. F. Soviet Phys. Proc. (Russian) 1967, 11, 349.
125. (c) Tsvirko, M. P.; Sapunov, V. V.; Soloviev, K. N. Opt. Spectrosc. (Russian) 1973, 34, 1094.
126. Also see: Kobayashi, N. In Phthalocyanines. Properties and Applications; Leznoff, C. C., Lever, A. B. P. Eds.; VCH Publishers: New York, 1993 and references therein.
127. (a) Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138.
128. (b) Bajema, L.; Gouterman, M.; Rose, C. J. Mol. Spectrosc. 1971, 39, 421.
129. (c) Aartsma, T. J.; Gouterman, M.; Jochum, C.; Kwiram, A. L.; Pepich, B. V.; Williams, L. D. J. Am. Chem. Soc. 1982, 104, 6278.
130. For examples, see: (a) Aaviksoo, J.; Frieberg, A.; Savikhin, S.; Stelmakh, G. F.; Tsvirko, M. P. Chem. Phys. Lett. 1984, 111, 275.
131. (b) Ehrenberg, B.; Johnson, F. M. Spectrochim. Acta 1990, 46a, 1521.
132. (c) Luo, B. Z.; Tian, M. Z.; Li, W. L.; Huang, S. H.; Yu, J. Q. J. Lumin. 1992, 53, 247.
133. (d) Vacha, M.; Machida, S.; Horie, K. Chem. Phys. Lett. 1995, 242, 169.
134. (e) Stiel, H.; Volkmer, A.; Ruckmann, I.; Zeug, A.; Ehrenberg, B.; Roder, B. Opt. Commun. 1998, 155, 135.
135. (f) Khodykin, O. V.; Zilker, S. J.; Haarer, D.; Kharlamov, B. M. Opt. Lett. 1999, 24, 513.
136. (g) Zhou, X.; Ren, A. M.; Feng, J. K.; Liu, X. J. Can. J. Chem. 2004, 82, 19.
137. Sapunov, V. V.; Solovev, K. N.; Kopranenkov, V. N.; Vorotnikov, A. M. Zh. Prikl. Spektrosk. 1986, 45, 56.
138. 41b that precise measurements of emission quantum yields in the range of the spectrum around 1 μm are difficult because of the rapidly fading sensitivity of the detection systems (PMTs). Therefore, the reported quantum yield values should be considered as approximate.
139. Tietze L. F.; Eicher, T. Reaktionen und Synthesen im organischchemischen Praktikum und Forschungslaboratorium; Georg Thieme Verlag: New York, 1991.
140. Novak, B. H.; Lash, T. D. J. Org. Chem. 1998, 63, 3998.
141. Toyota, M.; Yokota, M.; Ihara, M. J. Am. Chem. Soc. 2001, 123, 1856.
142. Hopkins, P. B.; Fuchs, P. L. J. Org. Chem. 1978, 43, 1208.