Novel core-modified expanded porphyrins with meso-aryl substituents: Synthesis, spectral and structural characterization

Journal of the American Chemical Society

Volumn 121, Issue 39, 1999, Pages 9053-9068

  Narayanan, Seenichamy Jeyaprakash ^a   Sridevi, Bashyam ^a   Chandrashekar, Tavarekere K ^a   Vij, Ashwani ^b   Roy, Raja ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b UNIVERSITY OF IDAHO   (United States)

^c CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032850669     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991472k     Document Type: Article

References (96)

1. (a) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins, Tetrahedron Organic Chemistry Series, Vol. 15; Pergamon: New York, 1997.
2. (b) Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
3. (a) Sessler, J. L.; Hemmi, G.; Mody, T. D.; Murai, T.; Burrell, A. K.; Young, S. W. Acc. Chem. Res. 1994, 27, 43-50.
4. (b) Maiya, B. G.; Cyr, M.; Harriman, A.; Sessler, J. L. J. Phys. Chem. 1990, 94, 3597-3601.
5. (c) Franck, B.; Nonn, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 1795-1811.
6. (d) Franck, B.; Fulling, M.; Gossmann, G.; Mertes, H.; Schroder, D. Proc. SPIE-Int. Soc. Opt. Eng. 1988, 997, 107-112.
7. (e) Shiau, F.-Y.; Liddell, P. A.; Vicente, G. H.; Ramana, N. V.; Ramachandran, K.; Lee, S.-J.; Pandey, R. K.; Dougherty, T. J.; Smith, K. M. SPIE Future Dir. Appl. Photodyn. Ther. 1989, 6, 17-86.
8. (f) Judy, M. L.; Matthews, J. L.; Newman, J. T.; Skiles, H.; Boriack, R.; Cyr, M.; Maiya, B, G.; Sessler, J. L. Photochem. Photobiol. 1991, 53, 101-107.
9. (g) Sessler, J. L.; Hemmi, G.; Maiya, B. G.; Harriman, A.; Judy, M. L.; Boriak, R.; Matthews, J. L.; Ehrenberg, B.; Malik, Z.; Nitzan, Y.; Ruck, A. Proc. SPIE-Int. Soc. Opt. Eng. 1991, 1426, 318-329.
10. (a) Sessler, J. L.; Murai, T.; Hemmi, G. Inorg. Chem. 1989, 28, 3390-3393.
11. (b) Sidhu, M. K.; Muller, H. H.; Miller, R. A.; Mody, T. D.; Hemmi, G.; Sessler, J. L.; Young, S. W. Abstracts of the 1991 National Meeting, American Associaton of University Radiologists, Orlando, FL, Mar 1991.
12. Burrell, A. K.; Sessler, J. L.; Cyr, M. J.; McGhee, E.; Ibers, J. A. Angew. Chem., Int. Ed. Engl. 1991, 30, 91-93.
13. (a) Sessler, J. L.; Andrievsky, A.; Genge, J. W. Adv. Supramol. Chem. 1997, 4, 97-142.
14. (b) Sessler, J. L.; Burrell, A. K.; Furuta, H.; Hemmi, G. W.; Iverson, B. L.; Kral, V.; Magda, D. J.; Mody, T. D.; Shreder, K.; Smith, D.; Weghorn, S. J. Transition Met. Supramol. Chem. 1994, 391-408.
15. (c) Sessler, J. L.; Sansom, P. I.; Andrievsky, A.; Kral, V. In Supramolecular Chemistry of Anions; Blanchi, A., James, K. B., Espana, E. G., Eds.; Wiley-VCH: New York,1997; pp 355-419.
16. (d) Shionoya, M.; Furuta, H.; Lynch, V.; Harriman, A.; Sessler, J. L. J. Am. Chem. Soc. 1992, 114, 5714-5722.
17. Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782-2785.
18. (7)(a) Franck, B.; Nonn, A.; Fuchs, K.; Gosmann, M. Liebigs. Ann. Chem. 1994, 503-510.
19. (b) Knubel, K.; Franck, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 1170-1172.
20. (a) Sessler, J. L.; Murai, T.; Lynch, V. Inorg. Chem. 1989, 28, 1333-1341.
21. (b) Burrell, A. K.; Hemmi, G.; Lynch, V.; Sessler, J. L. J. Am. Chem. Soc. 1991, 113, 4690-4692.
22. (c) Sessler, J. L.; Mody, T. D.; Hemmi, G.; Lynch, V. Inorg. Chem. 1993, 32, 3175-3187.
23. Sessler, J. L.; Weghorn, S. J.; Hiseada, Y.; Lynch, V. Chem. Eur. J. 1995, 1, 56-67.
24. (e) Sessler, J. L.; Burrell, A. K.; Lisowski, J.; Gebauer, A.; Cyr, M. J.; Lynch, V. Bull. Chem. Soc. Fr. 1996, 133, 725-734.
25. (f) Sessler, J. L.; Gebauer, A.; Guba, A.; Scherer, M.; Lynch, V. Inorg. Chem. 1998, 37, 2073-2076.
26. (a) Bauer, V. J.; Clive, D. L. J.; Dolphin, D.; Paine, J. B., III; Harris, F. L.; King, M. M.; Loder, J.; Wang, S. C.; Woodward, R. B. J. Am. Chem. Soc. 1983, 105, 6429-6436.
27. (b) Broadhurst, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1972, 2111-2116.
28. Lee, C.-H.; Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440.
29. (a) Heo, P.-Y.; Shin, K.; Lee, C.-H. Tetrahedron Lett. 1996, 37, 197-200.
30. (b) Bruckner, C.; Stenberg, E. D.; Boyle, R. W.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1997, 1689-1690.
31. (c) Sridevi, B.; Narayanan, S. J.; Srinivasan, A.; Reddy, M. V.; Chandrashekar, T. K. J. Porphyrins Phthalocyanines 1998, 2, 69-78.
32. Sessler, J. L.; Cyr, M. J.; Lynch, V.; McGhee, E.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 2810-2813.
33. Rexhausen, H.; Gossauer, A. J. Chem. Soc., Chem. Commun. 1983, 275.
34. Gossauer, A. Bull. Soc. Chim. Belg. 1983, 92, 793-795.
35. Sessler, J. L.; Weghorn, S. J.; Morishima, T.; Rosingana, M.; Lynch, V.; Lee, V. J. Am. Chem. Soc. 1992, 114, 8306-8307.
36. Sessler, J. L.; Morishima, T.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1991, 30, 977-980.
37. (a) Vogel, E.; Broring, M.; Fink, J.; Rosen, D.; Schmickler, H.; Lex, J.; Chan, K. W. K.; Wu, Y.-D.; Plattner, D. A.; Nendel, M.; Houk, K. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 2511-2514.
38. (b) Broring, M.; Jendrny, J.; Zander, L.; Schmickler, H.; Lex, J.; Wu, Y.-D.; Plattner, D. A.; Houk, K. N.; Vogel, E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2515-2517.
39. Sessler, J. L.; Weghorn, S. J.; Lynch, V.; Johnson, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1509-1512.
40. (a) Dolphin, D.; Rettig, S. J.; Tang, H.; Wijesekera, T.; Xie, L. Y. J. Am. Chem. Soc. 1993, 115, 9301-9302.
41. (b) Dolphin, D.; Xie, L. Y. J. Chem. Soc., Chem. Commun. 1994, 1475-1476.
42. (c) Xie, L. Y.; Boyle, R. W.; Dolphin, D. J. Am. Chem. Soc. 1996, 118, 4853-4859.
43. (d) Boyle, R. W.; Xie, L. Y.; Dolphin, D. Tetrahedron Lett. 1994, 35, 5377-5380.
44. Maiya, B. G.; Harriman, A.; Sessler, J. L.; Hemmi, G.; Murai, T.; Mallouk, T. E. J. Phys. Chem. 1989, 93, 8111-8115.
45. (a) Hariman, A.; Maiya, B. G.; Murai, T.; Hemmi, G.; Sessler, J. L.; Mallouk, T. E. J. Chem. Soc., Chem. Commun. 1989, 314-316.
46. (b) Levanon, H.; Regev, A.; Michaeli, S.; Galili, T.; Cyr, M.; Sessler, J. L. Chem. Phys. Lett. 1990, 174, 235-240.
47. (c) Regev, A.; Michaeli, S.; Levanon, H.; Cyr, M.; Sessler, J. L. J. Phys. Chem. 1991, 95, 9121-9129.
48. (d) Bachmann, R.; Gerson, F.; Putz, C.; Vogel, E. J. Chem. Soc., Perkin Trans. 2 1996, 541-546.
49. (e) Srinivasan, A.; Kumar, M. R.; Pandian, R. P.; Mahajan, S.; Pushpan, K. S.; Sridevi, B.; Narayanan, S. J.; Chandrashekar, T. K. J. Porphyrins Phthalocyanines 1998, 2, 1-10.
50. (a) Ravikanth, M.; Chandrashekar, T. K. Struct. Bonding (Berlin) 1995, 82, 105-188.
51. (b) Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, pp 1-165.
52. (a) Sessler, J. L.; Cyr, M.; Burrell, A. K. Tedrahedron 1992, 48, 9661-9672.
53. (b) Lisowski, J.; Sessler, J. L.; Lynch, V. Inorg. Chem. 1995, 34, 3567-3572.
54. (c) Sessler, J. L.; Gebauer, A.; Hoehner, M. C.; Lynch, V. J. Chem. Soc., Chem. Commun. 1998, 1835-1836.
55. Sessler, J. L.; Hoehner, M. C.; Gebauer, A.; Andrievsky, A.; Lynch, V. J. Org. Chem. 1997, 62, 9251-9260.
56. (a) Miller, D. C.; Johnson, M. R.; Becker, J. J.; Ibers, J. A. J. Heterocycl. Chem. 1993, 30, 1485-1490.
57. (b) Johnson, M. R.; Miller, D. C.; Bush, K.; Becker, J. J.; Ibers, J. A. J. Org. Chem. 1992, 57, 4414-4417.
58. (c) Miller, D. C.; Johnson, M. R.; Ibers, J. A. J. Org. Chem 1994, 59, 2877-2879.
59. (a) Hu, Z.; Kelley, C. S.; Cava, M. P. Tetrahedron Lett. 1993, 34, 1879-1882.
60. (b) Hu, Z.; Atwood, J. L.; Cava, M. P. J. Org. Chem. 1994, 59, 8071-8075.
61. (a) Vogel, E.; Pohl, M.; Herrmann, A.; Wiss, T.; Konig, C.; Lex, J.; Gross, M.; Gisselbrecht, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1520-1524.
62. (b) Vogel, E.; Frode, C.; Breihan, A.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2609-2612.
63. (a) Markl, G.; Striebl, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1333-1355.
64. (b) Markl, G.; Sauer, H.; Kreitmeier, P.; Burgemeister, T.; Kastner, F.; Adolin, G.; Noth, H.; Polborn, K. Angew. Chem., Int. Ed. Engl. 1994, 35, 1151-1153.
65. (c) Vogel, E. Pure Appl. Chem. 1993, 65, 143.
66. (d) Markl, G.; Striebl, U.; Knorr, A.; Porsch, M.; Daub, J. Tetrahedron Lett. 1995, 36, 4401.
67. (e) Markl, G.; Knott, T.; Kreitmeir, P.; Burgemeister, T.; Kastner, F. Tetrahedron 1996, 52, 11763.
68. Lash, T. D.; Richter, D. T. J. Am. Chem. Soc. 1998, 120, 9965-9966.
69. Latos-Grazynski, L.; Rachlewicz, K. Chem. Eur. J. 1995, 1, 68-72.
70. (a) Sessler, J. L.; Lisowski, J.; Boudreaux, K. A.; Lynch, V.; Barry, J.; Kodadek, T. J. J. Org. Chem. 1995, 60, 5975-5978.
71. (b) Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Keamey, P. E.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827-836.
72. (a) Srinivasan, A.; Reddy, M. V.; Narayanan, S. J.; Sridevi, B.; Pushpan, S. K.; Kumar, M. R.; Chandrashekar, T. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2598-2601.
73. (b) Srinivasan, A.; Mahajan, S.; Pushpan, S. K.; Kumar, M. R.; Chandrashekar, T. K. Tetrahedron Lett. 1998, 39, 1961-1964.
74. (c) Pushpan, S. K.; Narayanan, S. J.; Srinivasan, A.; Mahajan, S.; Chandrashekar, T. K.; Roy, R. Tetrahedron Lett. 1998, 39, 9249-9252.
75. Narayanan, S. J.; Sridevi, B.; Chandrashekar, T. K.; Vij, A.; Roy, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 3394-3397.
76. Gosmann, M.; Franck, B. Angew. Chem., Int. Ed. Engl. 1986, 25, 1100-1101.
77. (a) Paolesse, R.; Licoccia, S.; Spagnoli, M.; Boschi, T.; Khoury, R. G.; Smith, K. M. J. Org. Chem. 1997, 62, 5133-5137.
78. (b) Licoccia, S.; Vona, M. L.; Paolesse, R. J. Org. Chem. 1998, 63, 3190-3195.
79. Lash, T. D.; Chaney, S. T.; Richter, D. T. J. Org. Chem. 1998, 63, 9076-9088 and references therein.
80. Rachlewicz, K.; Sprutta, N.; Chmielewski, P. J.; Latos-Grazynski, L. J. Chem. Soc., Perkin Trans 2 1998, 969-975.
81. X-ray structures of both 13 and 14 have been solved. 13 shows a nonplanar structure (N2 -0.0171, N3 -0.0041, N1 0.0145, N4 0.0120 Å) with a P1 space group. There are two crystallographically independent molecules in the unit cell. 14 shows a nearly planar structure (N1 0.0155, N2 -0.0039, N3 -0.0046, O1 -0.0051 Å) with small deviations. The structural details will be published separately.
82. Compound 14 behaves differently with respect to coordination towards transition metals. For example, the X-ray structure of the Ni(II) complex shows coordination of all three pyrrole nitrogens and the furan oxygen, while in the Rh(I) complex, only one amino and one imino nitrogen are coordinated. The details of the structure will be published separately.
83. Rachlewicz, K.; Sprutta, N.; Latos-Grazynski, L.; Chmielewski, P. J.; Szterenberg, L. J. Chem. Soc., Perkin Trans 2 1998, 959-967.
84. Narayanan, S. J.; Sridevi, B.; Srinivasan, A.; Chandrashekar, T. K.; Roy, R. Tetrahedron Lett. 1998, 39, 7389-7392.
85. (a) Crossley, M. J.; Field, L. D.; Harding, M. M.; Sternhell, S. J. Am. Chem. Soc. 1987, 109, 2335-2341.
86. (b) Vogel, E.; Kocher, M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1986, 25, 257-259.
87. (c) Wehrle, B.; Limbach, H.-H.; Kocher, M.; Ermer, O.; Vogel, E. Angew. Chem., Int. Ed. Engl. 1987, 26, 934-936.
88. (d) Braun, J.; Schlabach, M.; Wehrle, B.; Kocher, M.; Vogel, E.; Limbach, H.-H. J. Am. Chem. Soc. 1994, 116, 6593-6604.
89. Doedens, R. J. Progress in Inorganic Chemistry; Lippard, S. J., Ed.; John Wiley & Sons: New York, 1976; 21, pp 209-231.
90. Preliminary X-ray structure of 17 suggests that the furan and the thiophene rings are inverted in the solid state.
91. Latos-Grazynski, L.; Lisowski, L.; Szterenberg, L.; Olmstead, M. M.; Balch, A. L. J. Org. Chem. 1991, 56, 4043-4045.
92. Latos-Grazynski, L.; Pacholska, E.; Chmielewski, P. J.; Olmstead, M. M.; Balch, A. L. Inorg. Chem. 1996, 35, 566-573.
93. (a) Franck, B. Angew. Chem., Int. Ed. Engl. 1982, 21, 343-353.
94. (b) Bringmann, G.; Franck, B. Liebigs Ann. Chem. 1982, 1272-1279.
95. (c) Tietze, L. F.; Geissler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1040-1042.
96. Vogel, E.; Dorr, J.; Herrmann, A.; Lex, J.; Schmickler, H.; Walgenbach, P.; Gisselbrecht, J. P.; Gross, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1597-1600.