Axially coordinated porphyrins as new rotaxane stoppers

Chemical Communications

Volumn , Issue 10, 2000, Pages 847-848

  Chichak, Kelly ^a   Walsh, M Catherine ^a   Branda, Neil R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(4,4' DIPYRIDINIUM)ETHANE; ALKANE DERIVATIVE; DIBENZO[24]CROWN 8 [2]PSEUDOROTAXANE; METALLOPORPHYRIN; RUTHENIUM DERIVATIVE; TAXANE DERIVATIVE; UNCLASSIFIED DRUG; [2]ROTAXANE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR MODEL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034697528     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001259i     Document Type: Article

References (25)

1. L. Flamigni, N. Armaroli, F. Barigelletti, J.-C. Chambron, J.-P. Sauvage and N. Solladie, New J. Chem., 1999, 23, 1151 and references therein.
2. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
3. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
4. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
5. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
6. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
7. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
8. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
9. Previously employed stoppers include: phosphines, S. J. Rowan and J. F. Stoddart, J. Am. Chem. Soc., 2000, 122, 164; calixarenes, C. Fischer, M. Nieger, O. Mogck, V. Bohmer, R. Ungaro and F. Vogtle, Eur. J. Org. Chem., 1998, 155; fullerenes, N. Armaroli, F. Diederich, C. O. Dietrich-Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten and J.-P. Sauvage, Chem. Eur. J., 1998, 4, 406; ferrocene, A. C. Benniston, A. Harriman and V. M. Lynch, J. Am. Chem. Soc., 1995, 117, 5275; saccharides, C. Kauffmann, W. M. Muller, F. Vogtle, S. Weinman, S. Abramson and B. Fuchs, Synthesis, 1999, 849; T. Schmidt, R. Schmieder, W. M. Muller, B. Kiupel and F. Vogtle, Eur. J. Org. Chem., 1998, 2003; dendrimers, D, B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Frechet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart and M. Venturi, J. Am. Chem. Soc., 1996, 118, 12 012; trityl, C. Heim, A. Affeld, M. Nieger and F. Vogtle, Helv. Chim. Acta., 1999, 82, 746.
10. F. M. Raymo, K. N. Houk and J. F. Stoddart, J. Am. Chem. Soc., 1998, 120, 9318.
11. S. J. Rowan and J. F. Stoddart, Org. Lett., 1999, 1, 1913; S. J. Cantrill, S. J. Rowan and J. F. Stoddart, Org. Lett., 1999, 1, 1363.
12. S. J. Rowan and J. F. Stoddart, Org. Lett., 1999, 1, 1913; S. J. Cantrill, S. J. Rowan and J. F. Stoddart, Org. Lett., 1999, 1, 1363.
13. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
14. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
15. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
16. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
17. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
18. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
19. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
20. For examples of using coordination chemistry to interlock rotaxanes, see: S. J. Loeb and J. A. Wisner, Chem. Commun., 1998, 2757; S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838; D. J. Cárdenas, P. Gaviña and J.-P. Sauvage, Chem. Commun., 1996, 1915; A. P. Lyon and D. H. Macartney, Inorg. Chem., 1997, 36, 729 and references therein. For examples to interlock catenanes, see: M. Fujita, Acc. Chem. Res., 1999, 32, 53; A. C. Try, M. M. Harding, D. G. Hamiltion and J. K. M. Sanders, Chem. Commun., 1998, 723. For examples to link rotaxanes into oligomers and necklaces, see: S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi and K. Kim, Angew. Chem., Int. Ed., 1999, 38, 638; D. Whang, K.-M. Park, J. Heo, P. Ashton and K. Kim, J. Am. Chem. Soc., 1998, 120, 4899.
21. N. Solladie, J.-C. Chambron and J.-P. Sauvage, J. Am. Chem. Soc., 1999, 121, 3684; M.-J. Blanco, M. C. Jimenez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; F. Vogtle, F. Ahuis, S. Baumann and J. L. Sessler, Liebigs Ann. Rec., 1996, 921; R. Ishin and A. E. Kaifer, J. Am. Chem. Soc., 1991, 113, 8188.
22. N. Solladie, J.-C. Chambron and J.-P. Sauvage, J. Am. Chem. Soc., 1999, 121, 3684; M.-J. Blanco, M. C. Jimenez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; F. Vogtle, F. Ahuis, S. Baumann and J. L. Sessler, Liebigs Ann. Rec., 1996, 921; R. Ishin and A. E. Kaifer, J. Am. Chem. Soc., 1991, 113, 8188.
23. N. Solladie, J.-C. Chambron and J.-P. Sauvage, J. Am. Chem. Soc., 1999, 121, 3684; M.-J. Blanco, M. C. Jimenez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; F. Vogtle, F. Ahuis, S. Baumann and J. L. Sessler, Liebigs Ann. Rec., 1996, 921; R. Ishin and A. E. Kaifer, J. Am. Chem. Soc., 1991, 113, 8188.
24. N. Solladie, J.-C. Chambron and J.-P. Sauvage, J. Am. Chem. Soc., 1999, 121, 3684; M.-J. Blanco, M. C. Jimenez, J.-C. Chambron, V. Heitz, M. Linke and J.-P. Sauvage, Chem. Soc. Rev., 1999, 28, 293; F. Vogtle, F. Ahuis, S. Baumann and J. L. Sessler, Liebigs Ann. Rec., 1996, 921; R. Ishin and A. E. Kaifer, J. Am. Chem. Soc., 1991, 113, 8188.
25. K. Chichak and N. R. Branda, Chem. Commun., 1999, 593.