Self-assembly of pyrrole-ferrocene hybrids, determined inter alia by a new chemically induced electrospray mass spectrometry technique

Chemistry - A European Journal

Volumn 4, Issue 1, 1998, Pages 152-158

  Scherer, Markus ^a   Sessler, Jonathan L ^a   Moini, Mehdi ^a   Gebauer, Andreas ^a   Lynch, Vincent ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Electrospray mass spectrometry; Ferrocenes; Pyrroles; Self assembly

Indexed keywords

MASS SPECTROMETRY; OLIGOMER;

EID: 0031934875     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(199801)4:1<152::aid-chem152>3.0.co;2-e     Document Type: Article

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5. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
6. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
7. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
8. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
9. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
10. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
11. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
12. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
13. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
14. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
15. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
16. a) Noncovalent dimers, trimers, and higher oligomers: R. S. Meissner, J. Rebek, Jr., J. de Mendoza, Science 1995, 270, 1485; N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85, and references therein: B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326; D. J. Cram, J. M. Cram, Container Molecules and their Guests, Graham, Cambridge, 1994; C. A. Hunter, L. D. Sarson, Angew. Chem. 1994, 106, 2424; Angew. Chem. Int. Ed. Engl. 1994, 33, 2313; M. S. Goodman, A. D. Hamilton, J. Weiss, J. Am. Chem. Soc. 1995, 117, 8447; J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479; J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. 1996, 108, 2347; Angew. Chem. Int. Ed. Engl. 1996, 35, 2204;
17. b) interlocked electron transfer molecules: for reviews, see: D. A. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725; J.-C Chambron, C. Dietrich-Buchecker, J.-P. Sauvage, in ref. [2], Vol. 9, 43;
18. b) interlocked electron transfer molecules: for reviews, see: D. A. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725; J.-C Chambron, C. Dietrich-Buchecker, J.-P. Sauvage, in ref. [2], Vol. 9, 43;
19. c) molecules capable of self-replication: E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997, and references therein; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880. and references therein; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221, and references therein; D. H. Lee, J. R. Granja, J. A. Martinez, K. S. Severin, M. R. Ghadiri, ibid. 1996, 382, 525;
20. molecules capable of self-replication: E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997, and references therein; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880. and references therein; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221, and references therein; D. H. Lee, J. R. Granja, J. A. Martinez, K. S. Severin, M. R. Ghadiri, ibid. 1996, 382, 525;
21. molecules capable of self-replication: E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997, and references therein; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880. and references therein; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221, and references therein; D. H. Lee, J. R. Granja, J. A. Martinez, K. S. Severin, M. R. Ghadiri, ibid. 1996, 382, 525;
22. molecules capable of self-replication: E. A. Wintner, B. Tsao, J. Rebek, Jr., J. Org. Chem. 1995, 60, 7997, and references therein; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, J. Am. Chem. Soc. 1996, 118, 6880. and references therein; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221, and references therein; D. H. Lee, J. R. Granja, J. A. Martinez, K. S. Severin, M. R. Ghadiri, ibid. 1996, 382, 525;
23. d) nanotubic peptides: J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43; M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301;
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25. e) oligonucleotide-based assemblies: C. Giovannangeli, J.-S. Sun, C. Hélène, in ref. [2], Vol. 4, 177; Y. Ohya, H. Noro, M. Komatsu, T. Ouchi, Chem. Lett. 1996, 447;
26. e) oligonucleotide-based assemblies: C. Giovannangeli, J.-S. Sun, C. Hélène, in ref. [2], Vol. 4, 177; Y. Ohya, H. Noro, M. Komatsu, T. Ouchi, Chem. Lett. 1996, 447;
27. f) self-assembled photoactive aggregates: H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772; J. L. Sessler, B. Wang, S. L. Springs, C. T. Brown, in ref. [2], Vol. 4, 311; V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, New York, 1991;
28. f) self-assembled photoactive aggregates: H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772; J. L. Sessler, B. Wang, S. L. Springs, C. T. Brown, in ref. [2], Vol. 4, 311; V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, New York, 1991;
29. f) self-assembled photoactive aggregates: H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772; J. L. Sessler, B. Wang, S. L. Springs, C. T. Brown, in ref. [2], Vol. 4, 311; V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, New York, 1991;
30. f) self-assembled photoactive aggregates: H. Tamiaki, T. Miyatake, R. Tanikaga, A. R. Holzwarth, K. Schaffner, Angew. Chem. 1996, 108, 810; Angew. Chem. Int. Ed. Engl. 1996, 35, 772; J. L. Sessler, B. Wang, S. L. Springs, C. T. Brown, in ref. [2], Vol. 4, 311; V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, New York, 1991;
31. g) three-dimensional structures such as helices: D. H. Apella, L. A. Christianson, I. L. Karle, D. R. Powell, J. Am. Chem. Soc. 1996, 118, 13071; D. Seebach, M. Overhand, F. N. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913; for an overview, see: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
32. g) three-dimensional structures such as helices: D. H. Apella, L. A. Christianson, I. L. Karle, D. R. Powell, J. Am. Chem. Soc. 1996, 118, 13071; D. Seebach, M. Overhand, F. N. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913; for an overview, see: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
33. g) three-dimensional structures such as helices: D. H. Apella, L. A. Christianson, I. L. Karle, D. R. Powell, J. Am. Chem. Soc. 1996, 118, 13071; D. Seebach, M. Overhand, F. N. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913; for an overview, see: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
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43. a) J. L. Sessler, A. K. Burrell, Top. Curr. Chem. 1991, 161. 177; V. Král, A. Andrievsky, J. L. Sessler, J. Am. Chem. Soc. 1995, 117, 2953; V. Král, S. L. Springs, J. L. Sessler, ibid. 1995, 117, 8881; V. Král, J. L. Sessler, H. Furuta, ibid. 1992, 114, 8704; M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, ibid. 1992, 114, 5714:
44. a) J. L. Sessler, A. K. Burrell, Top. Curr. Chem. 1991, 161. 177; V. Král, A. Andrievsky, J. L. Sessler, J. Am. Chem. Soc. 1995, 117, 2953; V. Král, S. L. Springs, J. L. Sessler, ibid. 1995, 117, 8881; V. Král, J. L. Sessler, H. Furuta, ibid. 1992, 114, 8704; M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, ibid. 1992, 114, 5714:
45. a) J. L. Sessler, A. K. Burrell, Top. Curr. Chem. 1991, 161. 177; V. Král, A. Andrievsky, J. L. Sessler, J. Am. Chem. Soc. 1995, 117, 2953; V. Král, S. L. Springs, J. L. Sessler, ibid. 1995, 117, 8881; V. Král, J. L. Sessler, H. Furuta, ibid. 1992, 114, 8704; M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, ibid. 1992, 114, 5714:
46. a) J. L. Sessler, A. K. Burrell, Top. Curr. Chem. 1991, 161. 177; V. Král, A. Andrievsky, J. L. Sessler, J. Am. Chem. Soc. 1995, 117, 2953; V. Král, S. L. Springs, J. L. Sessler, ibid. 1995, 117, 8881; V. Král, J. L. Sessler, H. Furuta, ibid. 1992, 114, 8704; M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, ibid. 1992, 114, 5714:
47. a) J. L. Sessler, A. K. Burrell, Top. Curr. Chem. 1991, 161. 177; V. Král, A. Andrievsky, J. L. Sessler, J. Am. Chem. Soc. 1995, 117, 2953; V. Král, S. L. Springs, J. L. Sessler, ibid. 1995, 117, 8881; V. Král, J. L. Sessler, H. Furuta, ibid. 1992, 114, 8704; M. Shionoya, H. Furuta, V. Lynch, A. Harriman, J. L. Sessler, ibid. 1992, 114, 5714:
48. b) P. A. Gale, J. L. Sessler, V. Král, V. Lynch, ibid. 1996, 118, 5140;
49. c) J. L. Sessler, A. Andrievsky, P. A. Gale, V. Lynch, Angew. Chem, 1996, 108, 2954; Angew. Chem. Int. Ed. Engl. 1996, 35, 2782.
50. J. L. Sessler, A. Andrievsky, P. A. Gale, V. Lynch, Angew. Chem, 1996, 108, 2954; Angew. Chem. Int. Ed. Engl. 1996, 35, 2782.
51. C. Li, J. C. Medina, G. E. Maguire, E. Abel, J. L. Atwood, G. Gokel, J. Am. Chem. Soc. 1997, 119, 1609.
52. a) A. N. Nesmeyanov, V. A. Sazonova, V. N. Drozd, Dokl. Akad. Nauk SSSR 1965, 165, 535;
53. b) H. Egger, K. Schlögl, Monatsh. Chem. 1964, 95, 1750;
54. c) G. A. Shvekhgeimer, V. I. Zvolinskii, M. Litim, P. B. Terentev, Metalloorg. Khim. 1992, 2, 376;
55. d) M. Puciová, P. Ertl, S. Toma, Collect. Czech. Chem. Commun. 1994, 59, 175;
56. e) for a pyrrolyle substituted ferrocene, see: A. Treibs, R. Zimmer-Galler, Chem. Ber. 1960, 93, 2539.
57. M. Scherer, J. L. Sessler, A. Gebauer, V. Lynch, J. Org. Chem., in press; this precursor (1) consists of a regioisomeric mixture of the 1-and 2-substituted cyclopentadiene species. Because these two isomers undergo deprotonation to yield the same anion during the synthesis of 3, a pre-separation of these materials is not required in the present instance.
58. In contrast to what is seen in the case of 3, the bond distances of the intermolecular H-bonds formed by the four pyrrolic subunits of 4 are not quite equal. Specifically, for 3, the geometry of the H-bonding interactions is as follows: N1 - H1 ⋯ O1, N ⋯O 2.947(6) Å, H ⋯ O 2.071(6) Å, N - H ⋯ O 164.1(5) °. By contrast, for 4, the relevant geometry of the interactions is: N1 - H1N ⋯ O3 (related by 2 - x, 1 -y, - z), N ⋯ O 2.922(9) Å, H⋯O 2.11(7) Å, N-H⋯O 151(7) °; N2-H2N ⋯ 02 (related by 2 - x, 1 - y, - z), N ⋯ O 2.877(9) Å, H ⋯ O 2.10(7) Å, N - H ⋯ O 135(5) °; N1′-H1′N ⋯ O3′ (related by - x, 1 - y, 1 - z), N ⋯ O 2.881(9) Å, H ⋯ O 2.15(7) Å, N - H ⋯ O 144(7) °; N2́ -H2′N ⋯ O2́ (related by - x, 1 - y, 1 - z), N ⋯ O 2.901(9) Å, H ⋯ O 2.10(7) Å, N - H ⋯ O 150(6) °.
59. The value of 3.45 Å given for the distance between the two pyrroles of a dipyrrolecyclopentadienyl is an average owing to the four slightly different sets of H-bonds in 4. It corresponds to the distance measured perpendicular to the plane of one pyrrole unit to the center of the adjacent one.
60. caled = 452).
61. a) J. A. Loo, R. R. Orgorzalek-Loo, H. R. Udseth, C. G. Edmonds, R. D. Smith, Rapid Commun. Mass Spectrom, 1991, 5, 582;
62. b) D. E. Clemmer, R. R. Hudgins. M. F. Jorrold, J. Am. Chem. Soc. 1995, 117, 10141;
63. c) R. Guevremont, K. W. M. Siu, J. C. Y. Le Blanc, S. S. Berman, J. Am. Soc. Mass Spectrom. 1992, 3, 216;
64. d) G. Hopfgartner, C. Piguet, J. D. Henion, A. F. Williams, Helv. Chim. Acta 1993, 76, 1759.
65. For an excellent overview, see: M. Przybylski, M. O. Glocker, Angew. Chem. 1996, 108, 878; Angew. Chem. Int. Ed. Engl. 1996, 35, 806, and references therein.
66. For an excellent overview, see: M. Przybylski, M. O. Glocker, Angew. Chem. 1996, 108, 878; Angew. Chem. Int. Ed. Engl. 1996, 35, 806, and references therein.
67. K. C. Russell, E. Leize, A. V. Dorsselaer, J.-M. Lehn, Angew. Chem. 1996, 107, 244; Angew. Chem. Int. Ed. Engl. 1995, 34, 209.
68. K. C. Russell, E. Leize, A. V. Dorsselaer, J.-M. Lehn, Angew. Chem. 1996, 107, 244; Angew. Chem. Int. Ed. Engl. 1995, 34, 209.
69. 2 as the solvent.
70. We conducted high-resolution ESMS-experiments as descibed in: a) S. Jackett, M. Moini, Rev Sci. Instrum. 1994, 65, 591;
71. b) L. Jiang, M. Moini, J. Am. Soc. Mass Spectrom. 1995, 6, 1256;
72. c) M. Moini, Rapid Commun. Mass Spectrom. 1994, 8, 711.
73. 2 should lead to lower levels of self-association.
74. 2 led to a substantial reduction in the intensity of those signals ascribable to the aggregated forms of 4, presumably as the result of charge repulsion effects. Even under these latter conditions, no peaks ascribable to doubly charged ions could be observed.
75. G. M. Sheldrick, SHELXTL/PC (Version 5.03). Siemens Analytical X-Ray Instruments, Madison. Wisconsin (USA) 1994.
76. International Tables for X-Ray Crystallography, Vol. C (Ed.: A. J. C. Wilson). Kluwer Academic, Boston, 1992.
77. S. M. Gadol, R. E. Davis, Organometallics 1982, 1, 1607.