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Volumn 119, Issue 21, 1997, Pages 4929-4933

Self-organized porphyrin dimer as a highly specific receptor for pyrazine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; PORPHYRIN DERIVATIVE; PYRAZINE DERIVATIVE;

EID: 0030904657     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963764g     Document Type: Article
Times cited : (71)

References (32)
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    • For other spontaneous dimeric porphyrin formation systems, see: (a) Aoyama Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143. (b) Segawa, H.; Takehara, C.; Honda, K.; Shimidzu, T.; Asahi, T.; Mataga, N. J. Phys. Chem. 1992, 96, 503. (c) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 243. (d) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111. (e) Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313. (f) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704.
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    • For other spontaneous dimeric porphyrin formation systems, see: (a) Aoyama Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143. (b) Segawa, H.; Takehara, C.; Honda, K.; Shimidzu, T.; Asahi, T.; Mataga, N. J. Phys. Chem. 1992, 96, 503. (c) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 243. (d) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111. (e) Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313. (f) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704.
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    • For other spontaneous dimeric porphyrin formation systems, see: (a) Aoyama Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143. (b) Segawa, H.; Takehara, C.; Honda, K.; Shimidzu, T.; Asahi, T.; Mataga, N. J. Phys. Chem. 1992, 96, 503. (c) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 243. (d) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111. (e) Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313. (f) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704.
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    • For other spontaneous dimeric porphyrin formation systems, see: (a) Aoyama Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143. (b) Segawa, H.; Takehara, C.; Honda, K.; Shimidzu, T.; Asahi, T.; Mataga, N. J. Phys. Chem. 1992, 96, 503. (c) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 243. (d) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111. (e) Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313. (f) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704.
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    • For other spontaneous dimeric porphyrin formation systems, see: (a) Aoyama Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143. (b) Segawa, H.; Takehara, C.; Honda, K.; Shimidzu, T.; Asahi, T.; Mataga, N. J. Phys. Chem. 1992, 96, 503. (c) Drain, C. M.; Fischer, R.; Nolen, E. G.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 243. (d) Kobuke, Y.; Miyaji, H. J. Am. Chem. Soc. 1994, 116, 4111. (e) Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2313. (f) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704.
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    • Following examples of large upfield shifts of bidentate ligands sandwiched by porphyrins are reported. (a) For 4,4′-bipyridyl covalently linked face-to-face porphyrin systems, see: Uemori, Y.; Nakatsubo, A.; Imai, H.; Nakagawa, S.; Kyuno, E. Inorg. Chem. 1992, 31, 5164. (b) For pyrazine polymeric porphyrin systems, see: Marvaud, V.; Launay, J. P. Inorg. Chem. 1993, 32, 1376.
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    • Uemori, Y.1    Nakatsubo, A.2    Imai, H.3    Nakagawa, S.4    Kyuno, E.5
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    • Following examples of large upfield shifts of bidentate ligands sandwiched by porphyrins are reported. (a) For 4,4′-bipyridyl covalently linked face-to-face porphyrin systems, see: Uemori, Y.; Nakatsubo, A.; Imai, H.; Nakagawa, S.; Kyuno, E. Inorg. Chem. 1992, 31, 5164. (b) For pyrazine polymeric porphyrin systems, see: Marvaud, V.; Launay, J. P. Inorg. Chem. 1993, 32, 1376.
    • (1993) Inorg. Chem. , vol.32 , pp. 1376
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    • note
    • 3 value, the curve-fitting analyses, in spite of excellent agreement between experimental and theoretical curves, results in poor standard deviations (over 50%) for the parameter. Therefore, only the order of magnitude is meaningful.
  • 31
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    • note
    • 2·L, where the ligands coordinate on Zn from outside of the dimer. These equilibrium processes, however, could not be separated by the present titration analyses.


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