Electrochemically controlled interactions between TTF-based dendrimers and an electron-rich oligomer

Chemical Communications

Volumn , Issue 24, 2002, Pages 2950-2951

  Beeby, Andrew ^a   Bryce, Martin R ^a   Christensen, Christian A ^a   Cooke, Graeme ^b   Duclairoir, Florence M A ^b   Rotello, Vincent M ^c  

^a DURHAM UNIVERSITY   (United Kingdom)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; OLIGOMER; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON; FLUORESCENCE SPECTROSCOPY; MOLECULAR INTERACTION; SUPRAMOLECULAR CHEMISTRY;

EID: 0036928825     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209765f     Document Type: Article

References (32)

1. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
2. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
3. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
4. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
5. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
6. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
7. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
8. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
9. For examples of recent reviews of electro-active dendrimers, see: (a) M. R. Bryce and W. Devonport, Advances in Dendritic Macromolecules, ed. G. R. Newkome, JAI Press, London, 1996, vol. 3, p. 115; (b) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni and M. Venturi, Acc. Chem. Res., 1998, 31, 26; (c) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; (d) A. E. Kaifer and M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, p. 207; (e) D. Astruc, J. C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor and C. Valerio, Dendrimers II, Top. Curr. Chem., 2000, 210, 229; (f) A. Juris, Electron Transfer in Chemistry, ed. V. Balzani, Wiley-VCH, Weinheim, 2001, vol. 3, p. 655; (g) S. Hecht and J. M. J. Fréchet, Angew. Chem., Int. Ed., 2001, 40, 79; (h) S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819; (i) C. B. Gorman and J. C. Smith, Acc. Chem. Res., 2001, 34, 60.
10. For examples, see: (a) R. Castro, I. Cuadrado, B. Alonso, C. M. Casado, M. Morán and A. E. Kaifer, J. Am. Chem. Soc., 1997, 119, 5760; (b) B. Gonález, C. M. Casado, B. Alonso, I. Cuadrado, M. Morán, Y. Wang and A. E. Kaifer, Chem. Commun., 1998, 2569; (c) C. M. Cardona, T. M. McCarley and A. E. Kaifer, J. Org. Chem., 2000, 65, 1857.
11. For examples, see: (a) R. Castro, I. Cuadrado, B. Alonso, C. M. Casado, M. Morán and A. E. Kaifer, J. Am. Chem. Soc., 1997, 119, 5760; (b) B. González, C. M. Casado, B. Alonso, I. Cuadrado, M. Morán, Y. Wang and A. E. Kaifer, Chem. Commun., 1998, 2569; (c) C. M. Cardona, T. M. McCarley and A. E. Kaifer, J. Org. Chem., 2000, 65, 1857.
12. For examples, see: (a) R. Castro, I. Cuadrado, B. Alonso, C. M. Casado, M. Morán and A. E. Kaifer, J. Am. Chem. Soc., 1997, 119, 5760; (b) B. González, C. M. Casado, B. Alonso, I. Cuadrado, M. Morán, Y. Wang and A. E. Kaifer, Chem. Commun., 1998, 2569; (c) C. M. Cardona, T. M. McCarley and A. E. Kaifer, J. Org. Chem., 2000, 65, 1857.
13. For examples, see: (a) P. J. Dandliker, F. Diederich, M. Gross, C. B. Knobler, A. Louati and E. M. Sanford, Angew. Chem., Int. Ed. Engl., 1994, 33, 1739; (b) R. Toba, J. M. Quintela, C. Peinador, E. Román and A. E. Kaifer, Chem. Commun., 2001, 857; (c) D. L. Stone, D. K. Smith and P. T. McGrail, J. Am. Chem. Soc., 2002, 124, 856.
14. For examples, see: (a) P. J. Dandliker, F. Diederich, M. Gross, C. B. Knobler, A. Louati and E. M. Sanford, Angew. Chem., Int. Ed. Engl., 1994, 33, 1739; (b) R. Toba, J. M. Quintela, C. Peinador, E. Román and A. E. Kaifer, Chem. Commun., 2001, 857; (c) D. L. Stone, D. K. Smith and P. T. McGrail, J. Am. Chem. Soc., 2002, 124, 856.
15. For examples, see: (a) P. J. Dandliker, F. Diederich, M. Gross, C. B. Knobler, A. Louati and E. M. Sanford, Angew. Chem., Int. Ed. Engl., 1994, 33, 1739; (b) R. Toba, J. M. Quintela, C. Peinador, E. Román and A. E. Kaifer, Chem. Commun., 2001, 857; (c) D. L. Stone, D. K. Smith and P. T. McGrail, J. Am. Chem. Soc., 2002, 124, 856.
16. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
17. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
18. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
19. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
20. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
21. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
22. For examples of TTF containing dendrimers, see: (a) M. R. Bryce, W. Devonport and A. J. Moore, Angew. Chem., Int. Ed., 1994, 33, 1761; (b) C. Wang, M. R. Bryce, A. S. Batsanov, L. Goldenberg and J. A. K. Howard, J. Mater. Chem., 1997, 7, 1189; (c) W. Devonport, M. R. Bryce, G. J. Marshallsay, A. J. Moore and L. M. Goldenberg, J. Mater. Chem., 1998, 8, 1361; (d) C. A. Christensen, L. M. Goldenberg, M. R. Bryce and J. Becher, Chem. Commun., 1998, 509; (e) M. R. Bryce, P. de Miguel and W. Devonport, Chem. Commun., 1998, 2565; (f) C. A. Christensen, M. R. Bryce and J. Becher, Synthesis, 2000, 12, 1695; (g) F. Le Derf, E. Levillain, G. Trippé, A. Gorgues, M. Sallé, R.-M. Sebastían, A.-M. Caminade and J.-P. Majoral, Angew. Chem., Int. Ed., 2001, 40, 224.
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25. -1. T = 21°C.
26. 42+ states.
27. 3CN 3:1) studies revealed negligible interactions between the neutral dendrimers and 3.
28. A similar decrease in peak current is often observed in the cyclic voltammograms of encapsulated redox-active units. For a review, see: C. M. Cardona, S. Mendoza and A. E. Kaifer, Chem. Soc. Rev., 2000, 29, 37.
29. 2+ and an electron rich macrocycle displaying similar electrochemical data, see: P. R. Ashton, V. Balzani, J. Becher, A. Credi, M. C. T. Fyfe, G. Mattersteig, S. Menzer, M. B. Nielsen, F. M. Raymo, J. F. Stoddart, M. Venturi and D. J. Williams, J. Am. Chem. Soc., 1999, 121, 3951.
30. Repeated electrochemical cycling (> 10 scans) resulted in a decrease in the peak currents for the radical cationic waves presumably due to the formation of an irreversible tangled aggregate.
31. H. A. de Cremiers, G. Clavier, F. Ilhan, G. Cooke and V. M. Rotello, Chem. Commun., 2001, 2232.
32. 6 in spectroscopic grade dichloromethane and acetonitrile (3:1 v/v).