Self-assembling covalently linked supramolecular arrays of defined structure: The remarkable redox reactivity of 15-meso-substituted 5-oxyporphyrins

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 21, 1996, Pages 2496-2499

  Khoury, Richard G ^a   Jaquinod, Laurent ^a   Nurco, Daniel J ^a   Pandey, Ravindra K ^a,b   Senge, Mathias O ^a,c   Smith, Kevin M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Dimerizations; Porphyrinoids; Redox reactions; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 0030471803     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199624961     Document Type: Article

References (28)

1. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
2. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
3. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
4. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
5. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
6. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
7. See for example a) D. E. Robertson, R. S. Farid, C. C. Moser, J. L. Urbauer, S. E. Mulholland, R. Pidikiti, J. D. Lear, A. J. Wand, W. F. DeGrado, P. L. Dutton, Nature (London) 1994, 368, 425; b) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196; Angew. Chem. Int. Ed. Engl. 1995, 34, 1096; D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611; c) K. M. Smith, L. A. Retires, J. Fajer, J. Am. Chem. Soc. 1983, 105, 1387; d) H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772.
8. See for example Supramolecular Assemblies - New Developments in Biofunctional Chemistry (Ed.: Y. Murakami), Mita Press, Tokyo, 1990; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
9. See for example Supramolecular Assemblies - New Developments in Biofunctional Chemistry (Ed.: Y. Murakami), Mita Press, Tokyo, 1990; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
10. See for example Supramolecular Assemblies - New Developments in Biofunctional Chemistry (Ed.: Y. Murakami), Mita Press, Tokyo, 1990; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
11. See for example Supramolecular Assemblies - New Developments in Biofunctional Chemistry (Ed.: Y. Murakami), Mita Press, Tokyo, 1990; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995; H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929; Angew. Chem. Int. Ed. Engl. 1995, 34, 849.
12. P. O'Carra in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, pp. 123-150, and references therein.
13. A. H. Jackson, G. W. Kenner, K. M. Smith, J. Chem. Soc. C 1968, 302.
14. J.-H. Fuhrhop, S. Besecke, J. Subramanian, J. Chem. Soc. Chem. Commun. 1973, 1.
15. See for example J.-H. Fuhrhop, S. Besecke, J. Subramanian, C. Mengersen, D. Riesner, D. Mauzerall, J. Am. Chem. Soc. 1975, 97, 7141; J.-H. Fuhrhop, E. Baumgartner, H. Bauer, ibid. 1981, 103, 5854; A. L. Balch, B. C. Noll, S. L. Phillips, S. M. Reid, E. P. Zovinka, Inorg. Chem. 1993, 32, 4730.
16. See for example J.-H. Fuhrhop, S. Besecke, J. Subramanian, C. Mengersen, D. Riesner, D. Mauzerall, J. Am. Chem. Soc. 1975, 97, 7141; J.-H. Fuhrhop, E. Baumgartner, H. Bauer, ibid. 1981, 103, 5854; A. L. Balch, B. C. Noll, S. L. Phillips, S. M. Reid, E. P. Zovinka, Inorg. Chem. 1993, 32, 4730.
17. See for example J.-H. Fuhrhop, S. Besecke, J. Subramanian, C. Mengersen, D. Riesner, D. Mauzerall, J. Am. Chem. Soc. 1975, 97, 7141; J.-H. Fuhrhop, E. Baumgartner, H. Bauer, ibid. 1981, 103, 5854; A. L. Balch, B. C. Noll, S. L. Phillips, S. M. Reid, E. P. Zovinka, Inorg. Chem. 1993, 32, 4730.
18. See for example K. M. Smith in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, p. 36, 40-41, 630, and references therein; R. Bonnett, M. J. Dimsdale, G. F. Stephenson, J. Chem. Soc. C 1969, 564; G. H. Barnett, M. F. Hudson, S. W. McCombie, K. M. Smith, J. Chem. Soc. Perkin Trans. 1 1973, 691.
19. See for example K. M. Smith in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, p. 36, 40-41, 630, and references therein; R. Bonnett, M. J. Dimsdale, G. F. Stephenson, J. Chem. Soc. C 1969, 564; G. H. Barnett, M. F. Hudson, S. W. McCombie, K. M. Smith, J. Chem. Soc. Perkin Trans. 1 1973, 691.
20. See for example K. M. Smith in Porphyrins and Metalloporphyrins (Ed.: K. M. Smith), Elsevier, Amsterdam, 1975, p. 36, 40-41, 630, and references therein; R. Bonnett, M. J. Dimsdale, G. F. Stephenson, J. Chem. Soc. C 1969, 564; G. H. Barnett, M. F. Hudson, S. W. McCombie, K. M. Smith, J. Chem. Soc. Perkin Trans. 1 1973, 691.
21. a) P. S. Clezy, A. J. Liepa, G. A. Smythe, Aust. J. Chem. 1970, 23, 603, 589;
22. b) R. G. Khoury, L. Jaquinod, D. J. Nurco, K. M. Smith, Chem. Commun. 1996, 1143.
23. D. A. Lee, J. M. Brisson, K. M. Smith, Heterocyeles 1995, 40, 131.
24. 2 using all independent data) by full matrix least squares methods (Siemens SHELXTL V. 5.03). R values are reported for R1 (based on observed data, 1 > 2σ) and wR2 (based on all data). Non-hydrogen atoms were refined with anisotropic thermal parameters. Hydrogens were placed in calculated positions refined with a riding model using isotropic thermal parameters. The crystal structure of 16 exhibited disorder in a small portion of the tetramer and in the solvate n-hexane. The datasets were corrected for absorption [11]. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-101. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: Int. code +(1223)336033; e-mail: teched@chemcrys.cam.ac.uk).
25. S. R. Parkin, B. Moezzi, H. Hope, J. Appl. Crystallogr. 1995, 28, 53.
26. a) J. L. Sessler, M. R. Johnson, S. F. Creager, J. C. Fettinger, J. A. Ibers, J. Am. Cem. Soc. 1990, 112, 9310;
27. b) R. K. Pandey, T. P. Forsyth, K. R. Gerzevske, J. J. Lin, K. M. Smith, Tetrahedron Lett. 1992, 33, 5315;
28. c) R. Paolesse, R. K. Pandey, T. P. Forsyth, L. Jaquinod, K. R. Gerzevske, D. J. Nurco, M. O. Senge, S. Liccocia, T. Boschi, K. M. Smith, J. Am. Chem. Soc. 1996, 118, 3869.