meso-aryl-substituted [26]hexaphyrin(1.1.0.1.1.0) and [38]nonaphyrin(1.1.0. 1.1.0.1.1.0) from oxidative coupling of a tripyrrane

Angewandte Chemie - International Edition

Volumn 44, Issue 15, 2005, Pages 2225-2229

  Shimizu, Soji ^a   Taniguchi, Ryuichiro ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Aromaticity; Hydrogen bonds; Macrocycles; Porphyrinoids; Protonation

Indexed keywords

ADDITION REACTIONS; CONFORMATIONS; NEGATIVE IONS; SUBSTITUTION REACTIONS;

ABSORPTION BANDS; CONFORMATIONAL CHANGES; PROTONATION; RUBYRIN 1; TRIPYRRANE;

ORGANIC COMPOUNDS;

EID: 17644395337     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200463054     Document Type: Article

References (32)

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22. Similar acid-promoted oxidative coupling of pyrroles has been shown to be quite effective in the synthesis of expanded porphyrins. See: a) J. L. Sessler, D. Seidel, V. Lynch, J. Am. Chem. Soc. 1999, 121, 11 257; b) D. Seidel, V. Lynch, J. L. Sessler, Angew. Chem. 2002, 114, 1480; Angew. Chem. Int. Ed. 2002, 41, 1422; c) T. Köhler, D. Seidel, V. Lynch, F. O. Arp, Z. Ou, K. M. Kadish, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 6872.
23. Similar acid-promoted oxidative coupling of pyrroles has been shown to be quite effective in the synthesis of expanded porphyrins. See: a) J. L. Sessler, D. Seidel, V. Lynch, J. Am. Chem. Soc. 1999, 121, 11 257; b) D. Seidel, V. Lynch, J. L. Sessler, Angew. Chem. 2002, 114, 1480; Angew. Chem. Int. Ed. 2002, 41, 1422; c) T. Köhler, D. Seidel, V. Lynch, F. O. Arp, Z. Ou, K. M. Kadish, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 6872.
24. Similar acid-promoted oxidative coupling of pyrroles has been shown to be quite effective in the synthesis of expanded porphyrins. See: a) J. L. Sessler, D. Seidel, V. Lynch, J. Am. Chem. Soc. 1999, 121, 11 257; b) D. Seidel, V. Lynch, J. L. Sessler, Angew. Chem. 2002, 114, 1480; Angew. Chem. Int. Ed. 2002, 41, 1422; c) T. Köhler, D. Seidel, V. Lynch, F. O. Arp, Z. Ou, K. M. Kadish, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 6872.
25. Similar acid-promoted oxidative coupling of pyrroles has been shown to be quite effective in the synthesis of expanded porphyrins. See: a) J. L. Sessler, D. Seidel, V. Lynch, J. Am. Chem. Soc. 1999, 121, 11 257; b) D. Seidel, V. Lynch, J. L. Sessler, Angew. Chem. 2002, 114, 1480; Angew. Chem. Int. Ed. 2002, 41, 1422; c) T. Köhler, D. Seidel, V. Lynch, F. O. Arp, Z. Ou, K. M. Kadish, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 6872.
26. w = 0.067, GOF = 1.275.
27. [2]
28. w = 0.087, GOF = 1.266.
29. w = 0.125, GOF = 1.045.
30. [4a]
31. [4a]
32. w (all data) = 0.2538, GOF = 1.041. CCDC 258963 (2), 258964 (2.2 TFA), 258965 (2.2 HCl), and 258966 (3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data_request/cif.