Regioselective β-metalation of meso-phosphanylporphyrins. Structure and optical properties of porphyrin dimers linked by peripherally fused phosphametallacycles

Journal of the American Chemical Society

Volumn 130, Issue 14, 2008, Pages 4588-4589

  Matano, Yoshihiro ^a   Matsumoto, Kazuaki ^a   Nakao, Yoshihide ^a   Uno, Hidemitsu ^b   Sakaki, Shigeyoshi ^a   Imahori, Hiroshi ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b EHIME UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL DERIVATIVE; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; ELECTROCHEMISTRY; GEOMETRY; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; QUANTITATIVE ANALYSIS; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 41849143015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710542e     Document Type: Article

References (23)

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15. Quite recently, Sugiura, Arnold, and co-workers reported the regioselective synthesis and crystal structure of β-HgCl-substituted porphyrins. See: Sugiura, K.-i.; Kato, A.; Iwasaski, K.; Miyasaka, H.; Yamashita, M.; Hino, S.; Arnold, D. P. Chem. Commun. 2007, 2046-2047.
16. Matano, Y.; Matsumoto, K.; Terasaka, Y.; Hotta, H.; Araki, Y.; Ito, O.; Shiro, M.; Sasasmori, T.; Tokitoh, N.; Imahori, H. Chem. Eur. J. 2007, 13, 891-901.
17. Arnold suggested the formation of a meso-phosphanylporphyrin as the intermediate in their synthesis of meso-phosphorylporphyrins. See: (a) Atefi, F.; Locos, O. B.; Senge, M. O.; Arnold, D. P. J. Porphyrins Phthalocyanines 2006, 10, 176-185.
18. (b) Atefi, F.; McMurtrie, J. C.; Turner, P.; Duriska, M.; Arnold, D. P. Inorg. Chem. 2006, 45, 6479-6489.
19. P-Pt = 2834 Hz), respectively.
20. w = 0.1690, R = 0.0691 (1>2.00σ(I)), GOF = 1.064. Although the quality of crystallographic data is not at the publishable level, a similar planar structure of 7a was confirmed by X-ray diffraction analysis.
21. The zinc atom is deviated from the 24-atom mean plane (0.32 Å) due to the coordination by the methanol-oxygen.
22. π orbital interaction between porphyrin and bridging Pd atom is important to lead to a broad Soret band of 8. For details, see the Supporting Information.
23. 3 (MeCN)]): +0.35/+0.60 V and -1.82 V for 5a; +0.42/+0.67 V and -1.71 V for 6a; +0.31/+0.37/+0.57 V and -1.83 V for 7a.