Porphyrin tessellation by design: Metal-mediated self-assembly of large arrays and tapes

Angewandte Chemie - International Edition

Volumn 37, Issue 17, 1998, Pages 2344-2347

  Drain, Charles Michael ^a   Nifiatis, Fotis ^a   Vasenko, Alexander ^a   Batteas, James D ^b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b NONE

Author keywords

Atomic force microscopy; Coordination chemistry; Nanostructures; Porphyrinoids; Supramolecular chemistry

Indexed keywords

EID: 0032544306     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980918)37:17<2344::AID-ANIE2344>3.0.CO;2-B     Document Type: Article

References (24)

1. a) J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VHC, Weinheim, 1995;
2. b) J. S. Lindsey, New J. Chem. 1991, 15, 153-180.
3. a) S. Anderson, H. L. Andersen, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 2247-2254;
4. b) D. L. Officer, A. K. Burrell, D. C. W. Reid, Chem. Commun. 1996, 1657-1658;
5. c) D. Fenyo, B. T. Chait, T. E. Johnson, J. S. Lindsey, J. Porphyrins Phthalocyanines 1997, 1, 93-99.
6. a) C. M. Drain, R. Fischer, E. Nolen, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1993, 243-245;
7. b) C. M. Drain, K. C. Russell, J.-M. Lehn, Chem. Commun. 1996, 337-338.
8. a) C. M. Drain, J.-M. Lehn, J. Chem. Soc.Chem. Commun. 1994, 2313-2315;
9. b) H. Yuan, L. Thomas, L. K. Woo, Inorg. Chem. 1996, 35, 2808-2817;
10. c) P. J. Stang, J. Fan, B. Olenyuk, Chem. Commun. 1997, 1453-1454;
11. d) R. V. Slone, J. T. Hupp, Inorg. Chem. 1997, 36, 5422-5437.
12. a) C. M. Drain, D. Mauzerall, Biophys. J. 1992, 63, 1556-1563;
13. b) K. Araki, M. J. Wagner, M. S. Wrighton, Langmuir 1996, 5393-5398.
14. K. Funatsu, A. Kimura, T. Imamura, Y. Sasaki, Chem. Lett. 1995, 765-766.
15. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
16. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
17. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
18. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
19. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
20. While coordination polymers have been known for many decades, the formation of discrete ordered coordination arrays is enjoying a renaissance: a) J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319; b) M. Fujita, Y. J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 1994, 116, 1151-1152; c) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097; d) B. Linton, A. D. Hamilton, Chem. Rev. 1997, 97, 1669-1680; e) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 507-518.
21. 3; see Figure 4 of the Supporting Informtion) for nonamer 5b formed from 1+2b+3b: α-pyridyl (δ=9.051→9.454), β-pyridyl (δ = 8.13 →8.32), tert-butyl (δ = 1.621 →1.627 and 1.634), pyrrole NH (δ = -2.816, -2.866, -2.906 →-2.786, -2.811, -2.840). The width at half-height of the methyl peaks broadens from about 2 Hz to 4.2 Hz.
22. 3 or mineral oil), 9a (14% in toluene), 10a (18% in toluene). The complete photophysical characterization of these systems will be reported elsewhere.
23. a) A. D. Adler, F. R. Longo, W. Shergalis, J. Am. Chem. Soc. 1964, 86, 3145-3148;
24. b) C. M. Drain, X. Gong, Chem. Commun. 1997, 2117-2118.