Synthesis and characterization of a directly linked N-confused porphyrin dimer

Angewandte Chemie - International Edition

Volumn 43, Issue 42, 2004, Pages 5655-5658

  Chmielewski, Piotr J ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

Dimerization; Nickel; Nitrogen heterocycles; Porphyrinoids; Supramolecular chemistry

Indexed keywords

CATALYSIS; CONDENSATION; DIMERS; MONOMERS; SYNTHESIS (CHEMICAL);

ELECTRONIC INTERACTION; PORPHYRIN SUBUNITS;

PORPHYRINS;

DIMER; NICKEL COMPLEX; PORPHYRIN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; COVALENT BOND; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 8444248938     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461361     Document Type: Article

References (44)

1. a) M. G. H. Vicente, L. Jaquinod, K. M. Smith, Chem. Commun. 1999, 1771;
2. b) A. Burrell, D. L. Officer, P. G. Plieger, D. C. W. Reid, Chem. Rev. 2001, 101, 2751.
3. a) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
4. b) R. W. Wagner, J. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759;
5. c) J.-S. Hsiao, B. P. Krueger, R. W. Wagner, T. E. Johnson, J. K. Delaney, D. C. Mauzerall, G. R. Fleming, J. S. Lindsey, D. F. Bocian, R. J. Donohoe, J. Am. Chem. Soc. 1996, 118, 11181;
6. d) S. I. Yang, J. Seth, T. Balasubramanian, D. Kim, J. S. Lindsey, D. Holten, D. F. Bocian, J. Am. Chem. Soc. 1999, 121, 4008.
7. a) J. P. Collman, Inorg. Chem. 1997, 36, 5145;
8. b) M. L. Merlau, M. P. Mejia, S. B. T. Nguen, J. T. Hupp, Angew. Chem. 2001, 113, 4369; Angew. Chem. Int. Ed. 2001, 40, 4239.
9. b) M. L. Merlau, M. P. Mejia, S. B. T. Nguen, J. T. Hupp, Angew. Chem. 2001, 113, 4369; Angew. Chem. Int. Ed. 2001, 40, 4239.
10. a) H. Segawa, D. Machida, Y. Senshu, J. Nakazaki, K. Hirakawa, F. Wu, Chem. Commun. 2002, 3032;
11. b) H. Segawa, Y. Senshu, J. Nakazaki, K. Susumu, J. Am. Chem. Soc. 2004, 126, 1354.
12. a) Y. Deng, C. K. Chang, D. G. Nocera, Angew. Chem. 2000, 112, 1108; Angew. Chem. Int. Ed. 2000, 39, 1066;
13. a) Y. Deng, C. K. Chang, D. G. Nocera, Angew. Chem. 2000, 112, 1108; Angew. Chem. Int. Ed. 2000, 39, 1066;
14. b) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057;
15. c) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
16. c) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
17. d) N. Yoshida, H. Shimidzu, A. Osuka, Chem. Lett. 1998, 55;
18. e) A. Nakano, A. Osuka, I. Yamazaki, T. Yamazaki, Y. Nishimura, Angew. Chem. 1998, 110, 3172; Angew. Chem. Int. Ed. 1998, 37, 3023;
19. e) A. Nakano, A. Osuka, I. Yamazaki, T. Yamazaki, Y. Nishimura, Angew. Chem. 1998, 110, 3172; Angew. Chem. Int. Ed. 1998, 37, 3023;
20. f) A. Nakano, H. Shimidzu, A. Osuka, Tetrahedron Lett. 1998, 39, 9489;
21. g) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Chem. Commun. 1998, 337;
22. h) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176;
23. h) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176;
24. i) N. Yoshida, A. Osuka, Tetrahedron Lett. 2000, 41, 9287;
25. j) A. Tsuda, A. Nakano, H. Furuta, H. Yamochi, A. Osuka, Angew. Chem. 2000, 112, 572; Angew. Chem. Int. Ed. 2000, 39, 558;
26. j) A. Tsuda, A. Nakano, H. Furuta, H. Yamochi, A. Osuka, Angew. Chem. 2000, 112, 572; Angew. Chem. Int. Ed. 2000, 39, 558;
27. k) A. Tsuda, Y. Nakamura, A. Osuka, Chem. Commun. 2003, 1096;
28. l) A. Tsuda, A. Osuka, Adv. Mater. 2002, 14, 75;
29. m) A. Takagi, Y. Yanagawa, A. Tsuda, N. Aratani, T. Matsumoto, A. Osuka, T. Kawai, Chem. Commun. 2003, 2986.
30. a) N. Aratani, A. Osuka, Y. H. Kim, D. H. Jeong, D. Kim, Angew. Chem. 2000, 112, 1517; Angew. Chem. Int. Ed. 2000, 39, 1458;
31. a) N. Aratani, A. Osuka, Y. H. Kim, D. H. Jeong, D. Kim, Angew. Chem. 2000, 112, 1517; Angew. Chem. Int. Ed. 2000, 39, 1458;
32. b) Y. H. Kim, D. H. Jeong, D. Kim, S. C. Jeoung, H. S. Cho, S. K. Kim, N. Aratani, A. Osuka, J. Am. Chem. Soc. 2001, 123, 76.
33. a) P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. 1994, 106, 805; Angew. Chem. Int. Ed. Engl. 1994, 33, 779;
34. a) P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. 1994, 106, 805; Angew. Chem. Int. Ed. Engl. 1994, 33, 779;
35. b) H. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 767;
36. c) G. R. Geier III, D. M. Haynes, J. S. Lindsey, Org. Lett. 1999, 1, 1455.
37. a) I. Schmidt, P. J. Chmielewski, Chem. Commun. 2002, 92;
38. b) I. Schmidt, P. J. Chmielewski, Z. Ciunik, J. Org. Chem. 2002, 67, 8917.
39. I. Schmidt, P. J. Chmielewski, Tetrahedron Lett. 2001, 42, 1151.
40. One of the decomposition products of 2 was identified as 3-(2′-(3′-p-tolylmethylpyrrole))-5,10,15,20-tetrakis(p-tolyl) -2-aza-21-carbaporphyrin by ESI-MS and NMR spectroscopy (see Supporting Information for details).
41. B. Krattinger, D. J. Nurco, K. M. Smith, Chem. Commun. 1998, 757.
42. H. Furuta, T. Ishizuka, A. Osuka, J. Am. Chem. Soc. 2002, 124, 5622.
43. I. Schmidt, P. J. Chmielewski, Inorg. Chem. 2003, 42, 5579.
44. K. M. Kadish, E. van Caemelbecke, G. Royal in The Porphyrin Handbook, Vol. 8 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, CA, 2000, pp. 1-114.