Anion binding properties of 5,5′-dicarboxamido-dipyrrolylmethanes

Organic and Biomolecular Chemistry

Volumn 2, Issue 20, 2004, Pages 2935-2941

  Vega, Ismael El Drubi ^a   Gale, Philip A ^a   Hursthouse, Michael B ^a   Light, Mark E ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CRYSTALLOGRAPHY; HYDROGEN BONDS; MIXTURES; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

ANION AFFINITIES; ANION RECEPTORS; BINDING PROPERTIES; OXO-ANIONS;

AROMATIC COMPOUNDS;

ANION; CARBOXYLIC ACID; PYRROLE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION;

ANIONS; CARBOXYLIC ACIDS; CRYSTALLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; SOLVENTS;

EID: 8344230653     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409115a     Document Type: Article

References (62)

1. S. Mangani and M. Ferraroni in Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James, K. García-España and E. García-España, Wiley-VCH, New York, 1997, pp. 63-78. For the crystal structure of porphobilinogen deaminase containing a dipyrrane unit binding a carboxylate group see: G. V. Louie, P. D. Brownlie, R. Lambert, J. B. Cooper, T. L. Blundell, S. P. Wood, M. J. Warren, S. C. Woodcock and P. M. Jordan, Nature, 1992, 359, 33-39. For a leading reference on the prodigiosins see: A. Fürstner, Angew. Chem. Int. Ed., 2003, 42, 3582-3603.
2. S. Mangani and M. Ferraroni in Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James, K. García-España and E. García-España, Wiley-VCH, New York, 1997, pp. 63-78. For the crystal structure of porphobilinogen deaminase containing a dipyrrane unit binding a carboxylate group see: G. V. Louie, P. D. Brownlie, R. Lambert, J. B. Cooper, T. L. Blundell, S. P. Wood, M. J. Warren, S. C. Woodcock and P. M. Jordan, Nature, 1992, 359, 33-39. For a leading reference on the prodigiosins see: A. Fürstner, Angew. Chem. Int. Ed., 2003, 42, 3582-3603.
3. S. Mangani and M. Ferraroni in Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James, K. García-España and E. García-España, Wiley-VCH, New York, 1997, pp. 63-78. For the crystal structure of porphobilinogen deaminase containing a dipyrrane unit binding a carboxylate group see: G. V. Louie, P. D. Brownlie, R. Lambert, J. B. Cooper, T. L. Blundell, S. P. Wood, M. J. Warren, S. C. Woodcock and P. M. Jordan, Nature, 1992, 359, 33-39. For a leading reference on the prodigiosins see: A. Fürstner, Angew. Chem. Int. Ed., 2003, 42, 3582-3603.
4. For information about vitrification of nuclear waste at the Hanford site see: V. Brown, Environ. Sci. Technol., 2003, 37, 16A-17A. For an article about anionic pollutants and eutrophication see: B. Moss, Chem. Ind., 1996, 407-411.
5. For information about vitrification of nuclear waste at the Hanford site see: V. Brown, Environ. Sci. Technol., 2003, 37, 16A-17A. For an article about anionic pollutants and eutrophication see: B. Moss, Chem. Ind., 1996, 407-411.
6. P. G. Plieger, P. A. Tasker and S. G. Galbraith, Dalton Trans., 2004, 313-318.
7. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
8. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
9. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
10. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
11. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
12. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
13. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
14. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
15. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
16. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
17. J. L. Sessler, M. J. Cyr, V. Lynch, E. McGhee and J. A. Ibers, J. Am. Chem. Soc., 1990, 112, 2810-2813; M. Shionoya, H. Furuta, V. Lynch, A. Harriman and J. L. Sessler, J. Am. Chem. Soc., 1992, 114, 5714-5722; V. Král, H. Furuta, K. Shreder, V. Lynch, V. Sessler and J. L. Sessler, J. Am. Chem. Soc., 1996, 118, 1595-1607; V. Kiál, A. Andrievsky and J. L. Sessler, J. Am. Chem. Soc., 1995, 117, 2953-2954; J. L. Sessler, A. Andrievsky, V. Král and V. Lynch, J. Am. Chem. Soc., 1997, 119, 9385-9392; H. Furuta, M. J. Cyr and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 6677-6678; J. L. Sessler, V. Král, J. W. Genge, R. E. Thomas and B. L. Iverson, Anal. Chem., 1998, 70, 2516-2522; J. L. Sessler, J. W. Genge, V. Král and B. L. Iverson, Supramol. Chem., 1996, 8, 45-52; B. L. Iverson, K. Shreder, V. Král and J. L. Sessler, J. Am. Chem. Soc., 1993, 115, 11022-11023; J. L. Sessler and S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford. 1997; J. L. Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17-55.
18. S. J. Coles, P. A. Gale and M. B. Hursthouse, Cryst. Eng. Comm., 2001, 53.
19. For an excellent recent review of anion receptors containing amide groups see: C. R. Bondy and S. J. Loeb, Coord. Chem. Rev., 2003, 240, 77-99; Also see: P. A. Gale, "Amide and Urea based anion receptors" in The Encyclopedia of Supramolecular Chemistry, ed. J. L. Atwood and J. W. Steed, Dekker, New York, in press.
20. For an excellent recent review of anion receptors containing amide groups see: C. R. Bondy and S. J. Loeb, Coord. Chem. Rev., 2003, 240, 77-99; Also see: P. A. Gale, "Amide and Urea based anion receptors" in The Encyclopedia of Supramolecular Chemistry, ed. J. L. Atwood and J. W. Steed, Dekker, New York, in press.
21. P. Chakrabarti, J. Mol. Biol., 1993, 234, 463-482.
22. For the crystal structure of the sulfate binding protein see: J. W. Pflugrath and F. A. Quiocho, Nature, 1985, 314, 257-260. Synthetic receptors containing cyclic polypeptides also have excellent oxo-anion receptor properties: S. Kubik, R. Kirchner, D. Nolting and J. Seidel, J. Am. Chem. Soc. 2002, 124, 12752-12760; S. Kubik and R. Goddard, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 5127-5132. For a recent sulfate selective receptor based on a platinum iso-quinoline complex appended with urea groups see: C. R. Bondy, P. A. Gale and S. J. Loeb, J. Am. Chem. Soc., 2004, 126, 5030-5031.
23. For the crystal structure of the sulfate binding protein see: J. W. Pflugrath and F. A. Quiocho, Nature, 1985, 314, 257-260. Synthetic receptors containing cyclic polypeptides also have excellent oxo-anion receptor properties: S. Kubik, R. Kirchner, D. Nolting and J. Seidel, J. Am. Chem. Soc. 2002, 124, 12752-12760; S. Kubik and R. Goddard, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 5127-5132. For a recent sulfate selective receptor based on a platinum iso-quinoline complex appended with urea groups see: C. R. Bondy, P. A. Gale and S. J. Loeb, J. Am. Chem. Soc., 2004, 126, 5030-5031.
24. For the crystal structure of the sulfate binding protein see: J. W. Pflugrath and F. A. Quiocho, Nature, 1985, 314, 257-260. Synthetic receptors containing cyclic polypeptides also have excellent oxo-anion receptor properties: S. Kubik, R. Kirchner, D. Nolting and J. Seidel, J. Am. Chem. Soc. 2002, 124, 12752-12760; S. Kubik and R. Goddard, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 5127-5132. For a recent sulfate selective receptor based on a platinum iso-quinoline complex appended with urea groups see: C. R. Bondy, P. A. Gale and S. J. Loeb, J. Am. Chem. Soc., 2004, 126, 5030-5031.
25. For the crystal structure of the sulfate binding protein see: J. W. Pflugrath and F. A. Quiocho, Nature, 1985, 314, 257-260. Synthetic receptors containing cyclic polypeptides also have excellent oxo-anion receptor properties: S. Kubik, R. Kirchner, D. Nolting and J. Seidel, J. Am. Chem. Soc. 2002, 124, 12752-12760; S. Kubik and R. Goddard, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 5127-5132. For a recent sulfate selective receptor based on a platinum iso-quinoline complex appended with urea groups see: C. R. Bondy, P. A. Gale and S. J. Loeb, J. Am. Chem. Soc., 2004, 126, 5030-5031.
26. J. L. Sessler, E. Katayev, G. D. Pantos and Y. A. Ustynyuk. Chem. Commun., 2004, 1276-1277.
27. C. Schmuck, Chem. Commun., 1999, 843-844; C. Schmuck, Chem. Eur. J., 2000, 6, 709-718; C. Schmuck and W. Wienand, J. Am. Chem. Soc., 2003, 125, 452-459.
28. C. Schmuck, Chem. Commun., 1999, 843-844; C. Schmuck, Chem. Eur. J., 2000, 6, 709-718; C. Schmuck and W. Wienand, J. Am. Chem. Soc., 2003, 125, 452-459.
29. C. Schmuck, Chem. Commun., 1999, 843-844; C. Schmuck, Chem. Eur. J., 2000, 6, 709-718; C. Schmuck and W. Wienand, J. Am. Chem. Soc., 2003, 125, 452-459.
30. K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H. Crabtree, J. Am. Chem. Soc., 1997, 119, 2325-2326; K. Kavallieratos, C. M. Bertao and R. H. Crabtree, J. Org. Chem., 1999, 64, 1675-1683.
31. K. Kavallieratos, S. R. de Gala, D. J. Austin and R. H. Crabtree, J. Am. Chem. Soc., 1997, 119, 2325-2326; K. Kavallieratos, C. M. Bertao and R. H. Crabtree, J. Org. Chem., 1999, 64, 1675-1683.
32. Y. H. Kim, J. Calabrese and C. McEwen, J. Am. Chem. Soc., 1996, 118, 1545-1546.
33. M. A. Hossain, J. M. Llinares, D. Powell and K. Bowman-James, Inorg. Chem., 2001, 40, 2936-2937; S. Camiolo, S. J. Coles, P. A. Gale, M. B. Hursthouse, T. A. Mayer and M. A. Paver, Chem. Commun., 2000, 275-276; S. J. Coles, J. G. Frey, P. A. Gale, M. B. Hursthouse, M. E. Light, K. Navakhun and G. L. Thomas, Chem. Commun., 2003, 568-569.
34. M. A. Hossain, J. M. Llinares, D. Powell and K. Bowman-James, Inorg. Chem., 2001, 40, 2936-2937; S. Camiolo, S. J. Coles, P. A. Gale, M. B. Hursthouse, T. A. Mayer and M. A. Paver, Chem. Commun., 2000, 275-276; S. J. Coles, J. G. Frey, P. A. Gale, M. B. Hursthouse, M. E. Light, K. Navakhun and G. L. Thomas, Chem. Commun., 2003, 568-569.
35. M. A. Hossain, J. M. Llinares, D. Powell and K. Bowman-James, Inorg. Chem., 2001, 40, 2936-2937; S. Camiolo, S. J. Coles, P. A. Gale, M. B. Hursthouse, T. A. Mayer and M. A. Paver, Chem. Commun., 2000, 275-276; S. J. Coles, J. G. Frey, P. A. Gale, M. B. Hursthouse, M. E. Light, K. Navakhun and G. L. Thomas, Chem. Commun., 2003, 568-569.
36. M. J. Deetz, M. Shang and B. D. Smith, J. Am. Chem. Soc., 2000, 122, 6201-6207; J. M. Mahoney, A. M. Beatty and B. D. Smith, J. Am. Chem. Soc., 2001, 123, 5847-5848.
37. M. J. Deetz, M. Shang and B. D. Smith, J. Am. Chem. Soc., 2000, 122, 6201-6207; J. M. Mahoney, A. M. Beatty and B. D. Smith, J. Am. Chem. Soc., 2001, 123, 5847-5848.
38. J. A. Wisner, P. D. Beer and M. G. B. Drew, Angew. Chem. Int. Ed., 2001, 40, 3606-3608; J. A. Wisner, P. D. Beer, M. G. B. Drew and M. R. Sambrook, J. Am. Chem. Soc., 2002, 124, 12469-12476.
39. J. A. Wisner, P. D. Beer and M. G. B. Drew, Angew. Chem. Int. Ed., 2001, 40, 3606-3608; J. A. Wisner, P. D. Beer, M. G. B. Drew and M. R. Sambrook, J. Am. Chem. Soc., 2002, 124, 12469-12476.
40. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
41. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
42. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
43. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
44. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
45. P. J. Smith, M. V. Reddington and C. S. Wilcox, Tetrahedron Lett., 1992, 33, 6085-6088; M. S. Goodman, V. Jubian and A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551-2554; E. K. Fan, C. Vicent and A. D. Hamilton, New J. Chem., 1997, 21, 81-85; A. Tejeda, A. I. Oliva, L. Simón, M. Grande, M. C. Caballero and J. R. Morán, Tetrahedron Lett., 2000, 41, 4563-4566; T. Tozawa, Y. Misawa, S. Tokita and Y. Kubo, Tetrahedron Lett., 2000, 41, 5219-5223; A. P. Davis and J. B. Joos, Coord. Chem. Rev., 2003, 240, 143-156.
46. S. Nishizawa, P. Bühlmann, M. Iwao and Y. Umezawa, Tetrahedron Lett., 1995, 36, 6483-6486.
47. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
48. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
49. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
50. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
51. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
52. P. A. Gale, S. Camiolo, C. P. Chapman, M. E. Light and M. B. Hursthouse, Tetrahedron Lett., 2001, 42, 5095-5097; P. A. Gale, S. Camiolo, G. J. Tizzard, C. P. Chapman, M. E. Light, S. J. Coles and M. B. Hursthouse, J. Org. Chem., 2001, 66, 7849-7853; G. Denuault, P. A. Gale, M. B. Hursthouse, M. E. Light and C. N. Warriner, New J. Chem., 2002, 811-813; S. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light and A. J. Shi, Chem. Commun., 2002, 758-759; P. A. Gale, K. Navakhun, S. Camiolo, M. E. Light and M. B. Hursthouse, J. Am. Chem. Soc., 2002, 124, 11228-11229; S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Org. Biomol. Chem., 2003, 1, 741-744.
53. S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Tetrahedron Lett., 2002, 43, 6995-6996.
54. The anion binding properties of compounds 1 and 2 have been communicated by us previously: I. El Drubi Vega, S. Camiolo, P. A. Gale, M. B. Hursthouse and M. E. Light, Chem. Commun., 2003, 1686-1687.
55. A. Basha, M. Lipton and S. M. Weinreb, Tetrahedron Lett., 1977, 48, 4171-4174.
56. NMR titration data were fitted to a binding model using EQNMR. See: M. J. Hynes, J. Chem. Soc., Dalton Trans., 1993, 311-312.
57. P. A. Gale, J. L. Sessler, V. Král and V. Lynch, J. Am. Chem. Soc., 1996, 118, 5140-5141.
58. D. A. Lightner, A. K. Tipton and D. A. Lightner, Monatsh. Chem., 2000, 131, 451-461.
59. A plethora of oligopyrrole-based solid state assemblies are reviewed in: J. L. Sessler, G. Berthon-Gelloz, P. A. Gale, S. Camiolo, E. V. Anslyn, P. Anzenbacher Jr., H. Furuta, G. J. Kirkovits, V. M. Lynch, H. Maeda, P. Morosini, M. Scherer, J. Shriver and R. S. Zimmerman, Polyhedron, 2003, 22, 2963-2983.
60. P. Job, Ann. Chim., 1928, 9, 113-203.
61. DFT structure calculated using Spartan '02: Spartan '02, Wavefunction Inc., Irvine CA, USA. See supplementary information for more details.
62. D. A. Leigh, J. K. Y. Wong, F. Dehez and F. Zerbetto, Nature, 2003, 424, 174-179.