Self-Assembly of Zinc Porphyrins around the Periphery of Hydrogen-Bonded Aggregates That Bear Imidazole Groups

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 8994-9000

  Simanek, Eric E ^a   Isaacs, Lyle ^a   Li, Xinhua ^a   Wang, Clay C C ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001550421     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615458     Document Type: Article

References (17)

1. Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 27, 37.
2. Seto, C. T.; Mathias, J. P.; Whitesides, G. M. J. Am. Chem. Soc. 1993, 115, 1321.
3. Chin, D. N.; Gordon, D. M.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 12033. Chin, D. N.; Simanek, E. E.; Li, X.; Wazeer, M. I. M.; Whitesides, G. M. J. Org. Chem. 1997, 62, 1891.
4. Chin, D. N.; Gordon, D. M.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 12033. Chin, D. N.; Simanek, E. E.; Li, X.; Wazeer, M. I. M.; Whitesides, G. M. J. Org. Chem. 1997, 62, 1891.
5. Kadish, K. M.; Shiue, L. R.; Rhodes, R. K.; Bottomley, L. A. Inorg. Chem. 1981, 20, 1274. Mashiko, T.; Dolphin, D. in Comprehensive Coordination Chemistry, Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: New York, 1987; Vol. 2, pp 813-898.
6. Kadish, K. M.; Shiue, L. R.; Rhodes, R. K.; Bottomley, L. A. Inorg. Chem. 1981, 20, 1274. Mashiko, T.; Dolphin, D. in Comprehensive Coordination Chemistry, Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: New York, 1987; Vol. 2, pp 813-898.
7. Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469 and references therein.
8. Lahiri, J.; Fate, G. D.; Ungashe, S. B.; Groves, J. T. J. Am. Chem. Soc. 1996, 118, 2347 and references therein.
9. Melamines and derivatives of CA containing covalently tethered porphyrins have been reported by a number of groups. See: Ichihara, K.; Naruta, Y. Chem. Lett. 1995, 631. Drain, C. M.; Russell, K. C.; Lehn, J.-M. Chem. Commun. 1996, 337. Drain, C. M.; Fischer, R.; Nolen, E.; Lehn, J.-M. J. Chem. Soc. Chem. Commun. 1993, 243 and references therein.
10. Melamines and derivatives of CA containing covalently tethered porphyrins have been reported by a number of groups. See: Ichihara, K.; Naruta, Y. Chem. Lett. 1995, 631. Drain, C. M.; Russell, K. C.; Lehn, J.-M. Chem. Commun. 1996, 337. Drain, C. M.; Fischer, R.; Nolen, E.; Lehn, J.-M. J. Chem. Soc. Chem. Commun. 1993, 243 and references therein.
11. Melamines and derivatives of CA containing covalently tethered porphyrins have been reported by a number of groups. See: Ichihara, K.; Naruta, Y. Chem. Lett. 1995, 631. Drain, C. M.; Russell, K. C.; Lehn, J.-M. Chem. Commun. 1996, 337. Drain, C. M.; Fischer, R.; Nolen, E.; Lehn, J.-M. J. Chem. Soc. Chem. Commun. 1993, 243 and references therein.
12. 1H NMR spectrum. These isomers have been investigated in: Simanek, E. E.; Wazeer, M. I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904.
13. 3 symmetry of the aggregate is maintained and that the structures of these imidazole-containing aggregates are very similar to those of 5 and 6. Assignment of all the resonances-especially those corresponding to the chelated imidazole group-are, therefore, tentative. The imide region of the spectrum, however, is diagnostic of the symmetry and number of aggregates present in solution.
14. (a) Cheng, X. H.; Gao, Q. Y.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. J. Org. Chem. 1996, 61, 2204-2206.
15. (b) Cheng, X. H.; Gao, Q. Y.; Smith, R. D.; Simanek, E. E.; Mammen, M.; Whitesides, G. M. Rapid Commun. Mass Spec. 1995, 9, 312-316.
16. 4PCl, may lead to spectra with fewer ambiguous lines.
17. For a more complete description of our use of GPC see ref 1 or: Mathias, J. P.; Seto, C. T.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 1725.