Collect. Czech. Chem. Commun. 2004, 69, 996-1008
https://doi.org/10.1135/cccc20040996

Six-Sided Heptaporphyrin Array: Towards a Nano-Sized Cube

Steven J. Langford* and Clint P. Woodward

School of Chemistry, Monash University, Clayton, Victoria 3800, Australia

References

1. Mongin O., Schuwey A., Vollot M.-A., Gossauer A.: Tetrahedron Lett. 1999, 40, 8347. <https://doi.org/10.1016/S0040-4039(99)01787-6>
2. Anderson H. L., Sanders J. K. M.: Angew. Chem., Int. Ed. Engl. 1990, 29, 1400. <https://doi.org/10.1002/anie.199014001>
3. Li J., Ambrose A., Yang S. I., Dier J. R., Seth J., Wack C. R., Bocian D. F., Holten D., Lindsey J. S.: J. Am. Chem. Soc. 1999, 121, 8927. <https://doi.org/10.1021/ja991730d>
4. Elemans J. A. A. W., Nolte R. J. M., Rowan A. E.: J. Porphyrins Phthalocyanines 2003, 7, 249. <https://doi.org/10.1142/S1088424603000331>
5. Takahashi R., Kobuke Y.: J. Am. Chem. Soc. 2003, 125, 2372. <https://doi.org/10.1021/ja028325y>
6. Alessio E., Macchi M., Heath S., Marzilli L. G.: Chem. Commun. 1996, 1411. <https://doi.org/10.1039/cc9960001411>
7. Slone R. V., Hupp J. T.: Inorg. Chem. 1997, 36, 5422. <https://doi.org/10.1021/ic9703991>
8. Fan J., Whiteford J. A., Olunyuk B., Levin M. D., Stang P. J., Fliescher E. B.: J. Am. Chem. Soc. 1999, 121, 2741. <https://doi.org/10.1021/ja9839825>
9. Drain C. M., Lehn J.-M.: J. Chem. Soc., Chem. Commun. 1994, 2312.
10. Maiya B. G., Bampos N., Kumar A. A., Feeder N., Sanders J. K. M.: New J. Chem. 2001, 25, 797. <https://doi.org/10.1039/b010148f>
11. Fallon G. D., Langford S. J., Lee M. A. P., Lygris E.: Inorg. Chem. Commun. 2002, 5, 715. <https://doi.org/10.1016/S1387-7003(02)00550-6>
12. Haycock R. A., Hunter C. A., James D. A., Michelsen U., Sutton L. R.: Org. Lett. 2000, 2, 2435. <https://doi.org/10.1021/ol000129d>
13a. Tsuda A., Hu H., Watanabe R., Aida T.: J. Porphyrins Phthalocyanines 2003, 7, 388. <https://doi.org/10.1142/S1088424603000501>
13b. Tsuda A., Nakamura T., Sakamoto S., Yamaguchi K., Osuka A.: Angew. Chem., Int. Ed. 2002, 41, 2817. <https://doi.org/10.1002/1521-3773(20020802)41:15<2817::AID-ANIE2817>3.0.CO;2-0>
14. Herein, we describe a proof-of-concept to orientating the six porphyrin faces of a cube. This example uses Ru(II) porphyrins which, despite their structural stability when compared to the more labile Zn(II) porphyrins, offer an electronic disadvantage for use in light harvesting arrays, since the Ru centre quenches singlet excitation energy. This may be overcome by using Zn(II) porphyrins for template direction in preparing restrictive cubes.
15. Jasat A., Sherman J. C.: Chem. Rev. 1999, 99, 931. <https://doi.org/10.1021/cr960048o>
16. For a recent example of a porphyrin cage, see: Fujita N., Biradha K., Fujita M., Sakamoto S., Yamaguchi K.: Angew. Chem., Int. Ed. 2001, 40, 1718. Preparing a cage from a restrictive cube by our template-directed approach would require removal of the template. <https://doi.org/10.1002/1521-3773(20010504)40:9<1718::AID-ANIE17180>3.0.CO;2-7>
17. Hawley J. C., Bampos N., Sanders J. K. M.: Chem. Eur. J. 2003, 9, 5211. <https://doi.org/10.1002/chem.200304862>
18. Crossley M. J., Thordarson P., Wu R. A.-S.: J. Chem. Soc., Perkin Trans. 1 2001, 2294. <https://doi.org/10.1039/b104846p>
19. Hawley J. C., Bampos N., Sanders J. K. M., Abraham R. J.: Chem. Commun. 1998, 661. <https://doi.org/10.1039/a709069b>
20. The distances were calculated using the Accelrys modelling package. For Ru(II) (porphyrin)– N(pyridine) distances, see: Giribabu L., Rao T. A., Maiya B. G.: Inorg. Chem. 1999, 38, 4971. <https://doi.org/10.1021/ic990326c>
21. Fallon G. D., Lee M. A. P., Langford S. J., Nichols P. J.: Org. Lett. 2002, 4, 1895. <https://doi.org/10.1021/ol025935u>
22. For a recent example, see: Guldi D. M., Da Ros T., Braiuca P., Prato M., Alessio E.: J. Mater. Chem. 2002, 12, 2001. <https://doi.org/10.1039/b202116a>