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Volumn 124, Issue 45, 2002, Pages 13474-13479

Quinoxaline-bridged porphyrinoids

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLES;

EID: 0037073214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0273750     Document Type: Article
Times cited : (197)

References (52)
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    • note
    • The two structures of 3b differ in the amount of solvent contained in the lattice but were otherwise quite similar, particularly in terms of the details of the macrocycle and its spatial arrangement.
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    • For molecular tubes based on π-stacking, see: (a) Laughlan, G.; Murchie, A. I. H.; Norman, D. G.; Moore, M. H.; Moody, P. C. E.; Lilley, D. M. J.; Luisi, B. Science 1994, 265, 520-524. (b) Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793-10800. (c) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (d) Shi, X.; Fettinger, J. C.; Davis, J. T. J. Am. Chem. Soc. 2001, 123, 6738-6739. (e) Matile, S. Chem. Soc. Rev. 2001, 30, 158-167.
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    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6738-6739
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    • For molecular tubes based on π-stacking, see: (a) Laughlan, G.; Murchie, A. I. H.; Norman, D. G.; Moore, M. H.; Moody, P. C. E.; Lilley, D. M. J.; Luisi, B. Science 1994, 265, 520-524. (b) Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793-10800. (c) Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067. (d) Shi, X.; Fettinger, J. C.; Davis, J. T. J. Am. Chem. Soc. 2001, 123, 6738-6739. (e) Matile, S. Chem. Soc. Rev. 2001, 30, 158-167.
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    • note
    • 3 are bound by Schiff-base-N (C-H···N, 3.271 Å) and the neighboring macrocycle-derived pyrrolyl-NH atoms (Cl···H-N, 3.706 Å.
  • 34
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    • note
    • 5a but remains an area of current interest and study.
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    • note
    • The binding constants for 3b-c and dihydrogenphosphate proved too low to measure accurately. So, in this report, only 3a was used for quantitative analyses involving this anion. The low affinities seen for 3b and 3c are consistent with the known electron-donating (and anion affinity reducing) ability of alkoxy groups. See: ref 7b.
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    • note
    • 2 were varied (cf. Supporting Information). Solubility considerations precluded carrying out similar studies in the case of systems 3a and 3b.
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    • - (see: Sharma, R. K.; Fry, J. L. J. Org. Chem. 1983, 48, 2112-2114). While this lack of purity potentially affects all anion binding analyses involving this species, the relative effects of impurities are likely to be similar for related species, allowing semiquantitative comparisons within generalized receptor classes (e.g., 1a vs 3a in the present instance).
    • (1983) J. Org. Chem. , vol.48 , pp. 2112-2114
    • Sharma, R.K.1    Fry, J.L.2
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    • note
    • 6b,c
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    • note
    • Because of the low solubility of 3a, it proved necessary to add DMSO in order to obtain solutions suitable for use in the colorimetric studies.
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