Electrochemical control of association and deposition of tetraviologen calix[4]resorcin

Russian Journal of Electrochemistry

Volumn 50, Issue 8, 2014, Pages 756-772

  Nasybullina, G R ^a   Yanilkin, V V ^a   Ziganshina, A Yu ^a   Morozov, V I ^a   Sultanova, E D ^a   Korshin, D E ^a   Milyukov, V A ^a   Shekurov, R P ^a   Konovalov, A I ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

association; calix 4 resorcin; electrochemical control; methylviologen; precipitation

Indexed keywords

ASSOCIATION REACTIONS; ELECTROLYTIC REDUCTION; PRECIPITATION (CHEMICAL);

CALIX[4]RESORCIN; ELECTROCHEMICAL CONTROL; METHYLVIOLOGEN; NEUTRAL STATE; RADICAL CATIONS; VIOLOGENS;

DEPOSITION;

EID: 84906267172     PISSN: 10231935     EISSN: 16083342     Source Type: Journal    
DOI: 10.1134/S1023193514080096     Document Type: Article

References (58)

1. Weitz, E.;Angew. Chem.;1954, vol. 66, p. 658.
2. Anelli, P.L.;Ashton, P.R.;Ballardini, R.;Balzani, V.;Delgaro, M.;Gandolfi, M.T.;Goodnow, T.T.;Kaifer, A.E.;Philp, D.;Pietraszkiewicz, M.;Prodi, L.;Reddington, M.V.;Slawin, A.M.Z.;Spencer, N.;Stoddart, J.F.;Vincent, C.;and Williams, D.J.;J. Am. Chem. Soc.;1992, vol. 114, p. 193.
3. Ashton, P.R.;Ballardini, R.;Balzani, V.;Credi, A.;Gandolfi, M.T.;Menzer, S.;Perez-Garcia, L.;Prodi, L.;Stoddart, J.F.;Venturi, M.;White, A.J.P.;and Williams, D.J.;J. Am. Chem. Soc.;1995, vol. 117, p. 11171.
4. Ballardini, R.;Balzani, V.;Credi, A.;Braun, C.L.;Gillard, R.E.;Montalti, M.;Philp, D.;Soddart, J.F.;Venturi, M.;White, A.J.P.;Williams, B.J.;and Williams, D.J.;J. Am. Chem. Soc.;1997, vol. 119, p. 12503.
5. Ashton, P.R.;Balzani, V.;Credi, A.;Kocian, O.;Pasini, D.;Prodi, L.;Spencer, N.;Stoddart, J.F.;Tolley, M.S.;Venturi, M.;White, A.J.P.;and Williams, D.J.;Chem. - Eur. J.;1998, vol. 4, p. 590.
6. Amabilino, D.B.;Ashton, P.R.;Balzani, V.;Boyd, S.E.;Credi, A.;Lee, J.U.;Menzer, S.;Stoddart, J.F.;Venturi, M.;and Williams, D.J.;J. Am. Chem. Soc.;1998, vol. 120, p. 4295.
7. Balzani, V.;Credi, A.;Langford, S.J.;Raymo, F.M.;Stoddart, J.F.;and Venturi, M.;J. Am. Chem. Soc.;2000, vol. 122, p. 3542.
8. Asakawa, M.;Ashton, P.R.;Balzani, V.;Credi, A.;Hamers, C.;Mattersteig, G.;Montalti, M.;Shipway, A.N.;Spencer, N.;Stoddart, J.F.;Tolley, M.S.;Venturi, M.;White, A.J.P.;and Williams, D.J.;Angew. Chem.;1998, vol. 110, p. 357.
9. Balzani, V.;Credi, A.;Mattersteig, G.;Matthews, O.A.;Raymo, F.M.;Stoddart, J.F.;Venturi, M.;White, A.J.P.;and Williams, D.J.;J. Org. Chem.;2000, vol. 65, p. 1924.
10. Deng, W.-Q.;Flood, A.H.;Stoddart, J.F.;and Goddart, W.A.;J. Am. Chem. Soc.;2005, vol. 127, p. 15994.
11. Ballardini, R.;Balzani, V.;Clemente-Leon, M.;Credi, A.;Gandolfi, M.T.;Ishow, E.;Perkins, J.;Stoddart, J.F.;Tseng, H.-R.;and Wenger, S.;J. Am. Chem. Soc.;2002, vol. 124, p. 12786.
12. Chen, Y.;Jung, G.-Y.;Ohlberg, D.A.A.;Li, X.;Stewart, D.R.;Jeppesen, J.O.;Nielsen, K.A.;Stoddart, J.F.;and Williams, R.S.;Nanotechnology, 2003, vol. 14, p. 462.
13. Bryce, M.R.;Cooke, G.;Duclairoir, F.M.A.;John, P.;Peperichka, D.F.;Polwart, N.;Rotello, V.M.;Stoddart, J.F.;and Tseng, H.-R.;J. Mater. Chem.;2003, vol. 13, p. 2111.
14. Venturi, M.;Dumas, S.;Balzani, V.;Cao, J.;and Stoddart, J.F.;New J. Chem.;2004, vol. 28, p. 1032.
15. Huang, T.J.;Tseng, H.-R.;Sha, L.;Lu, W.;Brough, B.;Flood, A.H.;Yu, B.-D.;Celestre, P.C.;Chang, J.P.;Stoddart, J.F.;and Ho, C.-M.;Nano Lett.;2004, vol. 4, p. 2065.
16. Liu, Y.;Flood, A.H.;Bonvallet, P.A.;Vignon, S.A.;Northrop, B.H.;Tseng, H.-R.;Jeppesen, J.O.;Huang, T.J.;Brough, B.;Baller, M.;Magonov, S.;Solares, S.D.;Goddard, W.A.;Ho, C.-M.;and Stoddart, J.F.;J. Am. Chem. Soc.;2005, vol. 127, p. 9745.
17. Nygaard, S.;Laursen, B.W.;Flood, A.H.;Hansen, C.N.;Jeppesen, J.O.;and Stoddart, J.F.;Chem. Commun.;2006, p. 144.
18. Beckman, R.;Beverly, K.;Boukai, A.;Bunimovich, Y.;Choi, J.W.;DeIonno, E.;Creen, J.;Johnston-Halperin, E.;Luo, Y.;Sheriff, B.;Stoddart, J.F.;and Heath, J.R.;Faraday Discuss.;2006, vol. 131, p. 9.
19. Diaz, M.C.;Illescas, B.M.;Martin, N.;Stoddart, J.F.;Canales, M.A.;Jimenez-Barbero, J.;Sarova, G.;and Guldi, D.M.;Tetrahedron, 2006, vol. 62, p. 1998.
20. Badjic, J.D.;Ronconi, C.M.;Stoddart, J.F.;Balzani, V.;Silvi, S.;and Credi, A.;J. Am. Chem. Soc.;2006, vol. 128, p. 1489.
21. Ikeda, T.;Saha, S.;Aprahamian, I.;Leung, K.C.-F.;Williams, A.;Deng, W.-Q.;Flood, A.H.;Goddard, W.A.;and Stoddart, J.F.;Chem. - Asian J.;2007, vol. 2, p. 76.
22. Flamigni, L.;Talarico, A.M.;Serroni, S.;Punterieoro, F.;Gunter, M.J.;Johnston, M.R.;and Jeynes, T.P.;Chem. Eur. J.;2003, vol. 9, p. 2649.
23. Gunter, M.J.;Eur. J. Org. Chem.;2004, p. 1655.
24. Steuerman, D.W.;Peters, A.J.;Tseng, H.-R.;Flood, A.H.;Jeppesen, J.;O.;Nielsen, K.A.;Heath, J.R.;and Stoddart, J.F.;Angew. Chem.;Int. Ed. Engl.;2004, vol. 43, p. 6486.
25. Flood, A.H.;Peters, A.J.;Vignon, S.A.;Steuerman, D.W.;Tseng, H.-R.;Kang, S.;Heath, J.R.;and Stoddart, J.F.;Chem. - Eur. J.;2004, vol. 10, p. 6558.
26. Tseng, H.-R.;Wu, D.;Fang, N.X.;Zhang, X.;and Stoddart, J.F.;ChemPhysChem, 2004, vol. 5, p. 111.
27. Amabilino, D.B.;Ashton, P.R.;Balzani, V.;Braun, C.L.;Credi, A.;Frecheu, J.M.J.;Leon, J.W.;Raymo, F.M.;Spencer, N.;Stoddart, J.F.;and Venturi, M.;J. Am. Chem. Soc.;1996, vol. 118, p. 12012.
28. Amabilino, D.B.;Asakawa, M.;Ashton, P.R.;Ballardini, R.;Balzani, V.;Belohradsky, M.;Credi, A.;Higuchi, M.;Raymo, F.M.;Shimizu, T.;Stoddart, J.F.;Venturi, M.;and Yase, K.;New J. Chem.;1998, vol. 22, p. 959.
29. Bissel, R.A.;Crdova, E.;Kaifer, A.E.;and Stoddart, J.F.;Nature, 1994, vol. 369, p. 133.
30. Yasuda, T.;Tanabe, K.;Tsuji, T.;Coti, K.K.;Aprahamian, I.;Stoddart, J.F.;and Kato, T.;Chem. Commun.;2010, vol. 46, p. 1224.
31. Ashton, P.R.;Ballardini, R.;Balzani, V.;Boyd, S.E.;Credi, A.;Gandolfi, M.T.;Gomez-Lopez, M.;Iqbal, S.;Philp, D.;Preece, J.A.;Prodi, L.;Ricketts, H.G.;Stoddart, J.F.;Tolley, M.S.;Venturi, M.;White, A.J.P.;and Williams, D.J.;Chem. - Eur. J.;1997, vol. 3, p. 152.
32. Tseng, H.-R.;Vignon, S.A.;and Stoddart, J.F.;Angew. Chem.;Int. Ed. Engl.;2003, vol. 42, p. 1491.
33. Liu, Y.;Flood, A.H.;and Stoddart, J.F.;J. Am. Chem. Soc.;2004, vol. 126, p. 9150.
34. Asakawa, M.;Ashton, P.R.;Balzani, V.;Credi, A.;Mattersteig, G.;Matthews, O.A.;Montalti, M.;Spencer, N.;Stoddart, J.F.;and Venturi, M.;Chem. Eur. J.;1997, vol. 3, p. 1992.
35. Ziganshina, A.Y.;Kharlamov, S.V.;Korshin, D.E.;Mukhitova, R.K.;Kazakova, E.Kh.;Latypov, Sh.K.;Yanilkin, V.V.;and Konovalov, A.I.;Tetrahedron Lett.;2008, vol. 49, p. 5312.
36. Nasybullina, G.R.;Yanilkin, V.V.;Nastapova, N.V.;Korshin, D.E.;Ziganshina, A.Y.;and Konovalov, A.I.;J. Inclusion Phenom. Macrocyclic Chem.;2012, vol. 72, p. 299.
37. Nasybullina, G.R.;Yanilkin, V.V.;Nastapova, N.V.;Ziganshina, A.Yu.;Korshin, D.E.;Spiridonova, Yu.S.;Karasik, A.A.;and Konovalov, A.I.;Izv. Akad. Nauk, Ser. Khim.;2012, p. 2274.
38. Yanilkin, V.V.;Mustafina, A.R.;Stepanov, A.S.;Nastapova, N.V.;Nasybullina, G.R.;Ziganshina, A.Y.;Solovieva, S.E.;and Konovalov, A.I.;Russ. J. Electrochem.;2011, vol. 47, p. 1082.
39. Ziganshina, A.Yu.;Nasybullina, G.R.;Yanilkin, V.V.;Nastapova, N.V.;Korshin, D.E.;Spiridonova, Yu.S.;Kashapov, R.R.;Grüner, M.;Habicher, W.D.;Karasik, A.A.;and Konovalov, A.I.;Russ. J. Electrochem.;2014, vol. 50, no. 2, pp. 142-153.
40. Kosower, E.M. and Hajdu, J.;J. Am. Chem. Soc.;1964, vol. 93, p. 2534.
41. Kimura, K.;Yamada, H.;and Tsubomura, H.;J. Chem. Phys.;1971, vol. 48, p. 440.
42. Itoh, M. and Kosower, E.M.;J. Am. Chem. Soc.;1968, vol. 90, p. 1843.
43. Kosower, E.M. and Teuerstein, A.;J. Am. Chem. Soc.;1976, vol. 98, p. 1586.
44. Weitz, E.;Ber. Dtsch. Chem. Ges.;1942, vol. 79, p. 1927.
45. Evans, A.G.;Evans, J.C.;and Baker, M.W.;J. Chem. Soc.;Perkin Trans. 2, 1977, p. 1787.
46. Evans, A.G.;Evans, J.C.;and Rees, N.H.;J. Chem. Soc.;Perkin Trans. 2, 1975, p. 1831.
47. Evans, A.G.;Dodson, N.K.;and Rees, N.H.;J. Chem. Soc.;Perkin Trans. 2, 1976, p. 859.
48. Bird, C.L. and Kuhn, A.T.;Chem. Soc. Rev.;1981, vol. 10, p. 49.
49. Jeon, W.S.;Ziganshina, A.Y.;Lee, J.W.;Ko, Y.H.;Kang, J.K.;Lee, C.;and Kim, K.;Angew. Chem.;Int. Ed. Engl.;2003, vol. 42, p. 4097.
50. Lee, J.W.;Hwang, I.;Jeon, W.S.;Ko, Y.H.;Sakamoto, S.;Yamaguchi, K.;and Kim, K.;Chem. Asian J.;2008, vol. 3, p. 1277.
51. Jeon, W.S.;Kim, E.;Ko, Y.H.;Hwang, I.;Lee, J.W.;Kim, S.-Y.;Kim, H.-J.;and Kim, K.;Angew. Chem.;Int. Ed. Engl.;2005, vol. 44, p. 87.
52. Zhu, Z.;Fahrenbach, A.C.;Li, H.;Barnes, J.C.;Liu, Z.;Dyar, S.M.;Zhang, H.;Lei, J.;Carmieli, R.;Sarjeant, A.A.;Stern, Ch.L.;Wasielewski, M.R.;and Stoddart, J.F.;J. Am. Chem. Soc.;2012, vol. 134, p. 11709.
53. Galus, Z.;Foundations of Electrochemical Analysis, New York: Harwood, 1976.
54. Shekurov, R.P.;Miluykov, V.A.;Islamov, D.R.;Krivolapov, D.B.;Kataeva, O.N.;Gerasimova, T.P.;Katsyuba, S.A.;Nasybullina, G.R.;Yanilkin, V.V.;and Sinyashin, O.G.;J. Organomet. Chem.;2014, vol. 766, p. 40.
55. Gordon, A.J. and Ford, R.A.;The Chemist's Companion, New York: Wiley-Interscience, 1972.
56. Peinador, C.;Roman, E.;Abboud, Kh.;and Kaifer, A.E.;Chem. Commun.;1999, p. 1887.
57. Roman, E.;Chas, M.;Quintela, J.M.;Peinador, C.;and Kaifer, A.E.;Tetrahedron, 2002, vol. 58, p. 699.
58. Johnson, C.S. and Gutowsky, H.S.;J. Chem. Phys.;1963, vol. 39, p. 58.