Synthesis and self-assembly of novel tetra- and hexapyrroles containing dipyrrins linked by a sulfur bridge at the β-position

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8413-8416

  Chen, Qingqi ^a   Zhang, Yongjun ^a   Dolphin, David ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Bis(dipyrrin 3 yl) sulfides; Dipyrrins; Helicates; Hexapyrrin; Metal complexes; Self assembly

Indexed keywords

BRIDGED COMPOUND; METAL COMPLEX; PYRROLE DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; CRYSTAL STRUCTURE; SYNTHESIS; X RAY ANALYSIS;

EID: 0037064530     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01958-5     Document Type: Article

References (28)

1. The Porphyrins, Dolphin, D., Ed.; Vol. 1 and Vol. 2, Academic Press, New York, 1978.
2. Falk H. The Chemistry of Linear Oligopyrroles and Bile Pigments. 1989;Springer Verlag, New York, Vienna.
3. Zhang Y., Thompson A., Rettig S.J., Dolphin D. J. Am. Chem. Soc. 120:1998;13537-13538.
4. Thompson A., Rettig S.J., Dolphin D. J. Chem. Soc., Chem. Commun. 1999;631-632.
5. Thompson A., Dolphin D. Org. Lett. 2000;1315-1318.
6. Thompson A., Dolphin D. J. Org. Chem. 65:2000;78870-78877.
7. Wärnmark K., Baxter P.N.W., Lehn J.-M. J. Chem. Soc., Chem. Commun. 1998;99-994.
8. Barigelletti F., Flamigni L., Calogero G., Hammarström L., Sauvage J.-P., Collin J.-P. J. Chem. Soc., Chem. Commun. 1998;2333-2334.
9. Weissbuch I., Baxter P.N.W., Cohen S., Cohen H., Kjaer K., Howes P.B., Als-Nielsen J., Hanan G.S., Schubert U.S., Lehn J.-M., Leiserowitz L., Lahav M. J. Am. Chem. Soc. 120:1998;4850-4860.
10. Garcia A.M., Romero-Salguero F.J., Bassani D.M., Lehn J.-M., Baum G., Fenske D. Chem. Eur. J. 5:1999;1803-1808.
11. Power K.N., Hennigar T.L., Zaworotko M.J. J. Chem. Soc., Chem. Commun. 1998;595-596.
12. Fujita M., Yu S.-Y., Kusukawa T., Funaki H., Ogura K., Yamaguchi K. Angew. Chem., Int. Ed. Engl. 37:1998;2082-2085.
13. Lehn J.-M., Rigault A. Angew. Chem., Int. Ed. Engl. 27:1988;1095-1097.
14. Yamamoto M., Takeuchi M., Shinkai S., Tani F., Naruta Y. J. Chem. Soc., Perkin Trans. 2. 2000;9-16.
15. Baxter P.N.W., Hanan G.S., Lehn J.-M. J. Chem. Soc., Chem. Commun. 1996;2019-2020.
16. Garcia A.M., Bassani D.M., Lehn J.-M., Baum G., Fenske D. Chem. Eur. J. 5:1999;1234-1238.
17. Funeriu D.P., Lehn J.-M., Baum G., Fenske D. Chem. Eur. J. 3:1997;99-104.
18. Whiteford J.A., Stang P.J., Huang S.D. Inorg. Chem. 37:1998;5595-55601.
19. Hasenknopf B., Lehn J.-M., Baum G., Kneisel B.O., Fenske D. Angew. Chem., Int. Ed. Engl. 35:1996;1838-1840.
20. Chen Q., Dolphin D. Synthesis. 2001;40-41.
21. 4S, C, 55.56; H, 6.22; N, 8.64. Found: C, 55.35; H, 6.40; N, 8.49%.
22. 4S, C, 54.20; H, 5.85; N, 9.03. Found: C, 54.10; H, 5.53; N, 8.79%.
23. 2=0.148. Calculations were performed using the teXscan structure analysis package (Molecular Structure Corporation, 1985-1997). CCDC 182/1158.
24. 2, required: C, 64.42; H, 6.18; N, 10.73. Found: C, 64.04; H, 6.39; N, 10.53%.
25. 4S, C, 60.00; H, 5.97; N, 10.37. Found C, 59.85; H, 5.49; N, 10.20%.
26. 4, required: C, 65.78; H, 6.57; N, 10.96. Found: C, 65.58; H, 6.37; N, 10.59%.
27. 4, required: C, 71.02; H, 6.60; N, 8.87. Found: C, 70.78; H, 6.39; N, 8.52%.
28. 2: C, 66.01; H, 6.15; N, 11.40. Found: C, 66.40; H, 6.05; N, 11.20%.