Abstract
Ni(II), Pd(II), and Cu(II) complexes of N-confused porphyrin (NCP) exhibit anion binding properties through a hydrogen bonding interaction at the peripheral NH of confused pyrrole ring. The binding constants of the tetrakis(pentafluorophenyl)-NCP metal complexes (1-M, M= Ni, Pd, Cu) for various halide anions in CH2C12 increase in the order of F− > Cl− > Br− > I−, respectively. Zwitterionic resonance form of the NCP complexes as well as interactions between halide anions and a pentafluorophenyl group are suggested to be important for efficient anion binding.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J.L. Sessler and S.J. Weghorn, Expanded, Contracted, and Isomeric Porphyrins, Elsevier, Oxford (1997), 520pp.; K.M. Kadish, K.M. Smith, and R. Guilard (eds.), The Porphyrin Handbook, Academic Press, San Diego (2000), Vol. 2.
H. Furuta, T. Asano, and T. Ogawa: J. Am. Chem. Soc. 116, 767 (1994).
P.J. Chmielewski, L. Latos-GraŻyński, K. Rachlewicz, and T. Głowiak: Angew. Chem., Int. Ed. Engl. 33, 779 (1994).
L. Latos-GraŻyński: In K.M. Kadish, K.M. Smith, and R. Guilard (eds.), The Porphyrin Handbook, Academic Press, San Diego (2000), Vol. 2, Chapter 14; H. Furuta, H. Maeda, and A. Osuka: Chem. Commun. 1795 (2002).
H. Furuta, N. Kubo, H. Maeda, T. Ishizuka, A. Osuka, H. Nanami, and T. Ogawa: Inorg. Chem. 39, 5424 (2000).
H. Furuta, T. Ishizuka, and A. Osuka: J. Am. Chem. Soc. 124, 5622 (2002); H. Furuta, K. Youfu, H. Maeda, and A. Osuka: Angew. Chem., Int. Ed. 42, 2186 (2003).
C.-H. Hung, W.-C. Chen, G.-H. Lee, and S.-M. Peng: Chem. Commun. 1516 (2002); J.D. Harvey and C.J. Ziegler, Chem. Commun. 1942 (2002).
H. Furuta, T. Ishizuka, A. Osuka, H. Dejima, H. Nakagawa, and Y. Ishikawa: J. Am. Chem. Soc. 123, 6207 (2001).
J.L. Sessler, S. Camiolo, and P.A. Gale: Coord. Chem. Rev. 240, 17 (2003).
W.-C. Chen and C.-H. Hung: Inorg. Chem. 40, 5070 (2001); J.-C. Liu, T. Ishizuka, A. Osuka, and H. Furuta: Chem. Commun. 1908 (2003).
H. Furuta, H. Maeda, and A. Osuka: J. Am. Chem. Soc. 122, 803 (2000); H. Maeda, A. Osuka, and H. Furuta: Supramol. Chem. 15, 447 (2003).
H. Maeda, A. Osuka, and H. Furuta: J. Am. Chem. Soc., 125, 15690 (2003).
H. Maeda, A. Osuka, Y. Ishikawa, I. Aritome, Y. Hisaeda, and H. Furuta: Org. Lett. 5, 1293 (2003).
H. Maeda, Y. Ishikawa, T. Matsuda, A. Osuka, and H. Furuta: J. Am. Chem. Soc. 125, 11822 (2003).
T.D. Lash: Synlett 279 (2000); Z. Xiao, B. O. Patrick, and D. Dolphin: Chem. Commun. 1816 (2002).
I. Alkorta, I. Rozas, and J. Elguero: J. Am. Chem. Soc. 124, 8593 (2002); D. Quiñ onero, C. Garau, C. Rotger, A. Frontera, P. Ballester, A. Costa, and P.M. Deyá: Angew. Chem., Int. Ed. 41, 3389 (2002).
H. Maeda, K. Youfu, A. Osuka, K. Yoza and H. Furuta: submitted.
Redox potentials (CuIII/CuII) using Br) and I) could not be estimated due to the overlap with the oxidation of anions themselves. K.A. Nielsen, J.O. Jeppesen, E. Levillain, and J. Becher: Angew. Chem., Int. Ed. 42, 187 (2003).
L. Fabbrizzi, M. Licchelli, S. Mascheroni, A. Poggi, D. Sacchi, and M. Zema: Inorg. Chem. 41, 6129 (2002).
T. Mizuno, W.-H. Wei, L. R. Eller, and J. L. Sessler: J.Am. Chem. Soc. 124, 1134 (2002).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Maeda, H., Osuka, A. & Furuta, H. Anion Binding Properties of N-Confused Porphyrins at the Peripheral Nitrogen. Journal of Inclusion Phenomena 49, 33–36 (2004). https://doi.org/10.1023/B:JIPH.0000031110.42096.d3
Issue Date:
DOI: https://doi.org/10.1023/B:JIPH.0000031110.42096.d3