Trans Doubly N-Confused Porphyrins: Cu(III) Complexation and Formation of Rodlike Hydrogen-Bonding Networks

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15690-15691

  Maeda, Hiromitsu ^a,b   Osuka, Atsuhiro ^b   Furuta, Hiroyuki ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COPPER; HYDROGEN; NITROGEN; PORPHYRIN; PYRROLE DERIVATIVE; SILVER;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0346995009     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038519t     Document Type: Article

References (23)

1. (a) Furuta, H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767-768.
2. (b) Chmielewski, P. J.; Latos-Grazyński, L.; Rachlewicz, K.; Głowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779-781.
3. (a) Furuta, H.; Maeda, H.; Osuka, A. Chem. Commun. 2002, 1795-1804.
4. (b) Latos-Grazyński, L. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: SanDiego, 2000; Vol. 2, Chapter 14.
5. (a) Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2000, 122, 803-807.
6. (b) Araki, K.; Winnischofer, H.; Toma, H. E.; Maeda, H.; Osuka, A.; Furuta, H. Inorg. Chem. 2001, 40, 2020-2025.
7. (c) Maeda, H.; Osuka, A.; Furuta, H. Supramol. Chem. 2003, 15, 447-450.
8. (a) Furuta, H.; Maeda, H.; Osuka, A. J. Org. Chem. 2000, 65, 4222-4226, 5450 (corrections).
9. (b) Furuta, H.; Maeda, H.; Osuka, A. J. Org. Chem. 2001, 66, 8563-8572.
10. Futura, H.; Ishizuka, T.; Osuka, A.; Ogawa, T. J. Am. Chem. Soc. 2000, 122, 5748-5757.
11. The most possible tautomeric form estimated by DFT calculations of 3 is shown in Scheme 1. See Supporting Information.
12. 5). Shin, J.-Y.; Furuta, H., Osuka, A. Angew. Chem., Int. Ed. 2001, 40, 619-621.
13. 3, R = 0.0985, wR (all data) = 0.3362, GOF = 1.271 (1 > 2σ(I)).
14. Crystal packing structure of 4a is shown in Supporting Information.
15. The similar aromatic inner 4H form is reported in "trans" -dicarbaporphyrins. (a) Lash, T. D.; Romanic, J. L.; Hayes, M. J.; Spence, J. D. Chem. Commun. 1999, 819-820.
16. (b) Lash, T. D. Synlett 1999, 279-295.
17. 3, Z = 4, R = 0.0792, wR (all data) = 0.2433, GOF = 0.968 (1 > 2σ(I)).
18. The corresponding values of cis-isomer (7): 67.71° and 2.924 Å.
19. Allen, W. E.; Fowler, C. J.; Lynch, V. M.; Sessler, J. L. Chem. Eur. J. 2001, 7, 721-729.
20. Maeda, H.; Ishikawa, Y.; Matsuda, T.; Osuka, A.; Furuta, H. J. Am. Chem. Soc. 2003, 125, 11822-11823.
21. 2CP (6) is shown to be an efficient photosensitizer for singlet oxygen. Araki, K.; Engelmann F. M.; Mayer, I.; Toma, H. E.; Baptista, M. S.; Maeda, H.; Osuka, A.; Furuta, H. Chem. Lett. 2003, 32, 244-245.
22. (a) Furuta, H.; Ishizuka, T.; Osuka, A. J. Am. Chem. Soc. 2002, 124. 5622-5623.
23. (b) Liu, J.-C.; Ishizuka, T.; Osuka, A.; Furuta, H. Chem. Commun. 2003, 1908-1909.