Doubly N-fused pentaphyrin

Angewandte Chemie - International Edition

Volumn 43, Issue 7, 2004, Pages 876-879

  Srinivasan, Alagar ^a   Ishizuka, Tomoya ^a   Furuta, Hiroyuki ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Aromaticity; Macrocyclic ligands; Oxidation; Porphyrinoids; Structure elucidation

Indexed keywords

CRYSTAL STRUCTURE; OXIDATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

PENTAPHYRIN; PYRROLE RINGS; TRIPENTACYCLIC RINGS;

AROMATIC HYDROCARBONS;

METHANOL DERIVATIVE; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 4544229128     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352946     Document Type: Article

References (18)

1. The Porphyrin Handbook, Vol. 2 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic, San Diego, 2000.
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4. b) P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Głowiak, Angew. Chem. 1994, 106, 805-808; Angew. Chem. Int. Ed. Engl. 1994, 33, 779-781;
5. c) H. Furuta, H. Maeda, A. Osuka, Chem. Commun. 2002, 1795-1804;
6. d) L. Latos-Grażyński in ref. [1], chapt. 14.
7. A. Srinivasan, T. Ishizuka, A. Osuka, H. Furuta, J. Am. Chem. Soc. 2003, 125, 878-879.
8. β-Alkyl meso-free pentaphyrins and their analogues are synthesized, see a) H. Rexhausen, A. Gossauer, J. Chem. Soc. Chem. Commun. 1983, 275;
9. b) A. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267-2340;
10. c) J. L. Sessler, S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Pergamon, New York, 1997.
11. J.-Y. Shin, H. Furuta, A. Osuka, Angew. Chem. 2001, 113, 639-641; Angew. Chem. Int. Ed. 2001, 40, 619-621.
12. J.-Y. Shin, H. Furuta, A. Osuka, Angew. Chem. 2001, 113, 639-641; Angew. Chem. Int. Ed. 2001, 40, 619-621.
13. a) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 1999, 121, 2945-2946;
14. b) H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 2000, 122, 5748-5757;
15. c) B. Kiran, M. H. Nguyen, J. Organomet. Chem. 2002, 643-644, 265-271.
16. It is noteworthy that the reported partially meso-aryl-substituted pentaphyrins were also quite unstable, even in the solid state, and decomposed when exposed to air with a half-live of several days: C. Brückner, E. D. Sternberg, R. W. Boyle, D. Dolphin, Chem. Commun. 1997, 1689-1690.
17. w = 0.057, GOF = 0.756. CCDC-219943 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
18. 5, which was twofold higher than that of the reported Rothemund-type synthesis; see ref. [5].