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Binding of 1,5-bis(p-sulfonatophenyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane with tetra(methyl viologen) calix[4]resorcinol

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Abstract

Binding of an amphiphilic dianion 1,5-bis(p-sulfonatophenyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane (APCO2−) with an amphiphilic octacation tetra(methyl viologen) calix[4]resorcinol (MVCA8+) in media containing different amounts of water and DMSO using NaClO4 or NaCl as supporting electrolytes was shown for the first time by cyclic voltammetry and spectrophotometry. The stoichiometry of the complex depends on the MVCA8+: APCO2− ratio, medium, and supporting electrolyte. A 1: 1 charge-transfer complex is mainly formed (λmax = 480 nm) in 30% DMSO at a ratio of the compounds of 1: 1. A similar 1: 1 complex of APCO2− with a model compound methyl viologen MV2+ (λmax = 482 nm) is formed under these conditions. A donor-acceptor interaction occurs between the acceptor viologen units and nitrogen-centered electron-donating fragments of the APCO2− dianion. An increase in the content of APCO2− in the solution leads to an additional binding of one (30 vol.% DMSO, water, NaClO4) or two (30 vol.% DMSO, water, NaCl) particles of APCO2− with the hydrophobic fragments of MVCA8+. The complexes aggregate to form insoluble precipitates in aqueous and water-DMSO media. A selective reversible electroswitching from the bound to free state of one of the three bound APCO2− particles was performed when reducing MVCA8+ to MVCA4·+ in a 30 vol.% DMSO/NaCl medium.

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References

  1. J. M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995, 281 pp.

    Book  Google Scholar 

  2. P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgaro, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vincent, D. J. Williams, J. Am. Chem. Soc., 1992, 114, 193.

    Article  CAS  Google Scholar 

  3. P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Perez-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc., 1995, 117, 11171.

    Article  Google Scholar 

  4. R. Ballardini, V. Balzani, A. Credi, C. L. Braun, R. E. Gillard, M. Montalti, D. Philp, J. F. Stoddart, M. Venturi, A. J. P. White, B. J. Williams, D. J. Williams, J. Am. Chem. Soc., 1997, 119, 12503.

    Article  CAS  Google Scholar 

  5. P. R. Ashton, V. Balzani, A. Credi, O. Kocian, D. Pasini, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Chem. Eur. J., 1998, 4, 590.

    Article  CAS  Google Scholar 

  6. D. B. Amabilino, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, J. U. Lee, S. Menzer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc., 1998, 120, 4295.

    Article  CAS  Google Scholar 

  7. V. Balzani, A. Credi, S. J. Langford, F. M. Raymo, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc., 2000, 122, 3542.

    Article  CAS  Google Scholar 

  8. M. Sakawa, P. R. Ashton, V. Balzani, A. Credi, C. Hamers, G. Mattersteig, M. Montalti, A. N. Shipway, N. Spencer, J. F. Stoddart, M. S. Tolley, M. Venturi, A. J. P. White, D. J. Williams, Angew. Chem., 1998, 110, 357.

    Article  Google Scholar 

  9. V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, F. M. Raymo, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Org. Chem., 2000, 65, 1924.

    Article  CAS  Google Scholar 

  10. R. Ballardini, V. Balzani, M. Clemente-Leon, A. Credi, M. T. Gandolfi, E. Ishow, J. Perkins, J. F. Stoddart, H.-R. Tseng, S. Wenger, J. Am. Chem. Soc., 2002, 124, 12786.

    Article  CAS  Google Scholar 

  11. Y. Chen, G.-Y. Jung, D. A. A. Ohlberg, X. Li, D. R. Stewart, J. O. Jeppesen, K. A. Nielsen, J. F. Stoddart, R. S. Williams, Nanotechnology, 2003, 14, 462.

    Article  CAS  Google Scholar 

  12. M. R. Bryce, G. Cooke, F. M. A. Duclairoir, P. John, D. F. Peperichka, N. Polwart, V. M. Rotello, J. F. Stoddart, H.-R. Tseng, J. Mater. Chem., 2003, 13, 2111.

    Article  CAS  Google Scholar 

  13. M. Venturi, S. Dumas, V. Balzani, J. Cao, J. F. Stoddart, New J. Chem., 2004, 28, 1032.

    Article  CAS  Google Scholar 

  14. Y. Liu, A. H. Flood, J. F. Stoddart, J. Am. Chem. Soc., 2004, 126, 9150.

    Article  CAS  Google Scholar 

  15. T. J. Huang, H.-R. Tseng, L. Sha, W. Lu, B. Brough, A. H. Flood, B.-D. Yu, P. C. Celestre, J. P. Chang, J. F. Stoddart, C.-M. Ho, Nano Lett., 2004, 4, 2065.

    Article  CAS  Google Scholar 

  16. Y. Liu, A. H. Flood, P. A. Bonvallet, S. A. Vignon, B. H. Northrop, H.-R. Tseng, J. O. Jeppesen, T. J. Huang, B. Brough, M. Baller, S. Magonov, S. D. Solares, W. A. Goddard, C.-M. Ho, J. F. Stoddart, J. Am. Chem. Soc., 2005, 127, 9745.

    Article  CAS  Google Scholar 

  17. S. Nygaard, B. W. Laursen, A. H. Flood, C. N. Hansen, J. O. Jeppesen, J. F. Stoddart, Chem. Commun., 2006, 144.

    Google Scholar 

  18. R. Beckman, K. Beverly, A. Boukai, Y. Bunimovich, J. W. Choi, E. DeIonno, J. Creen, E. Johnston-Halperin, Y. Luo, B. Sheriff, J. F. Stoddart, J. R. Heath, Faraday Discuss., 2006, 131, 9.

    Article  CAS  Google Scholar 

  19. M. C. Diaz, B. M. Illescas, N. Martin, J. F. Stoddart, M. A. Canales, J. Jimenez-Barbero, G. Sarova, D. M. Guldi, Tetrahedron, 2006, 62, 1998.

    Article  CAS  Google Scholar 

  20. J. D. Badjic, C. M. Ronconi, J. F. Stoddart, V. Balzani, S. Silvi, A. Credi, J. Am. Chem. Soc., 2006, 128, 1489.

    Article  CAS  Google Scholar 

  21. V. V. Yanilkin, Elektrokhimiya makrotsiklicheskikh soedinenii, in Elektrokhimiya organicheskikh soedinenii v nachale XXI veka [Electrochemistry of Macrocyclic Compounds. Electrochemistry of Organic Compounds at the Beginning of the XXI Century], Eds V. P. Gul’tyai, A. G. Krivenko, A. P. Tomilov, Kompaniya Sputnik, Moscow, 2008, 378 (in Russian).

    Google Scholar 

  22. A. H. Flood, A. J. Peters, S. A. Vignon, D. W. Steuerman, H.-R. Tseng, S. Kang, J. R. Heath, J. F. Stoddart, Chem. Eur. J., 2004, 10, 6558.

    Article  CAS  Google Scholar 

  23. H.-R. Tseng, D. Wu, N. X. Fang, X. Zhang, J. F. Stoddart, Chem. Phys. Chem., 2004, 5, 111.

    Article  CAS  Google Scholar 

  24. D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Braun, A. Credi, J. M. J. Frecheu, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc., 1996, 118, 12012.

    Article  CAS  Google Scholar 

  25. D. B. Amabilino, M. Asakawa, P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, A. Credi, M. Higuchi, F. M. Raymo, T. Shimizu, J. F. Stoddart, M. Venturi, K. Yase, New J. Chem., 1998, 22, 959.

    Article  CAS  Google Scholar 

  26. F. Le Derf, M. Mazari, N. Mercier, E. Levillain, G. Trippe, A. Riou, P. Richomme, J. Becher, J. Carin, J. Orduna, N. Gallego-Planas, A. Gorgues, M. Salle, Chem. Eur. J., 2001, 7, 447.

    Article  Google Scholar 

  27. V. V. Yanilkin, N. V. Nastapova, V. A. Mamedov, A. A. Kalinin, V. P. Gubskaya, Elektrokhimiya, 2007, 43, 808 [Russ. J. Electrochem. (Engl. Transl.), 2007, 43, 770].

    Google Scholar 

  28. V. V. Yanilkin, N. V. Nastapova, A. S. Stepanov, V. A. Mamedov, A. A. Kalinin, Russ. Chem. Bull., Int. Ed., 2009, 58, 89 [Izv. Akad. Nauk, Ser. Khim., 2009, 89].

    Article  CAS  Google Scholar 

  29. P. D. Beer, P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 487.

    Article  Google Scholar 

  30. J. M. Lloris, R. Martinez-Manez, J. Soto, T. Pardo, J. Organomet. Chem., 2001, 637–639, 151.

    Article  Google Scholar 

  31. J. Yoon, S. K. Kim, N. J. Singh, K. S. Kim, Chem. Soc. Rev., 2006, 35, 355.

    Article  CAS  Google Scholar 

  32. T. Matsue, T. Kato, U. Akiba, T. Osa, Chem. Lett., 1985, 14, 1825.

    Article  Google Scholar 

  33. S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem., Int. Ed., 2001, 40, 2119.

    Article  CAS  Google Scholar 

  34. H.-J. Kim, W. S. Jeon, Yo H. Ko, K. Kim, Proc. Natl Acad. Sci., 2002, 99, 5007.

    Article  CAS  Google Scholar 

  35. M. Rekharsky, Yo Inoue, Solvation Effects in Guest Binding, in Encyclopedia of Supramolecular Chemistry, Eds J. L. Atwood, J. W. Steed, Marcel Dekker, New York, 2004, 393 pp.

    Google Scholar 

  36. F. Pina, A. J. Parola, Coord. Chem. Rev., 1999, 185–186, 149.

    Article  Google Scholar 

  37. V. V. Yanilkin, I. S. Ryzhkina, V. I. Morozov, K. M. Enikeev, A. R. Burilov, L. A. Kudryavtseva, A. I. Konovalov, Zh. Obshch. Khim., 2001, 71, 409 [Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71, 373].

    Google Scholar 

  38. I. S. Ryzhkina, V. V. Yanilkin, V. I. Morozov, L. A. Kudryavtseva, A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 858 [Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72, 802].

    Google Scholar 

  39. I. S. Ryzhkina, V. V. Yanilkin, V. I. Morozov, L. A. Kudryavtseva, A. I. Konovalov, Zh. Fiz. Khim., 2003, 77, 491 [Russ. J. Phys. Chem. (Engl. Transl.), 2003, 77, 426].

    CAS  Google Scholar 

  40. V. V. Yanilkin, I. S. Ryzhkina, N. V. Nastapova, Ya. A. Babkina, A. R. Burilov, V. I. Morozov, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2003, 52, 1142 [Izv. Akad. Nauk, Ser. Khim., 2003, 1082].

    Article  CAS  Google Scholar 

  41. E. Kh. Kazakova, A. V. Prosvirkin, V. V. Yanilkin, R. Froehlich, W. D. Habicher, J. Inclus. Phenomena, 2003, 47, 149.

    Article  CAS  Google Scholar 

  42. A. R. Mustafina, V. V. Skripacheva, A. T. Gubaidullin, S. K. Latipov, A. V. Toropchina, V. V. Yanilkin, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, Inorg. Chem., 2005, 44, 4017.

    Article  CAS  Google Scholar 

  43. A. R. Mustafina, V. V. Skripacheva, V. A. Burilov, A. T. Gubaidullin, N. V. Nastapova, V. V. Yanilkin, S. E. Solovéva, I. S. Antipin, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2008, 57, 1897 [Izv. Akad. Nauk, Ser. Khim., 2008, 1863].

    Article  CAS  Google Scholar 

  44. A. E. Kaifer, M. Gomez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, 1999, 256 pp.

    Book  Google Scholar 

  45. P. L. Boulas, M. Gomez-Kaifer, L. Echegoyen, Angew. Chem., Int. Ed., 1998, 37, 216.

    Article  CAS  Google Scholar 

  46. A. Niemz, V. M. Rotello, Acc. Chem. Res., 1999, 32, 44.

    Article  CAS  Google Scholar 

  47. A. E. Kaifer, Acc. Chem. Res., 1999, 32, 62.

    Article  CAS  Google Scholar 

  48. P. D. Beer, P. A. Gale, G. Z. Chen, J. Chem. Soc., Dalton Trans., 1999, 1897.

    Google Scholar 

  49. J. Alvares, Y. Wang, M. Gomes-Kaifer, A. E. Kaifer, Chem. Commun., 1998, 1455.

    Google Scholar 

  50. Y. Wang, J. Alvarez, A. E. Kaifer, Chem. Commun., 1998, 1457.

    Google Scholar 

  51. V. V. Skripacheva, A. R. Mustafina, N. V. Rusakova, V. V. Yanilkin, N. V. Nastapova, R. R. Amirov, V. A. Burilov, R. R. Zairov, S. S. Kost, S. E. Solovieva, Yu. V. Korovin, I. S. Antipin, A. I. Konovalov, Eur. J. Inorg. Chem., 2008, 3957.

    Google Scholar 

  52. N. V. Nastapova, A. S. Stepanov, V. V. Yanilkin, V. A. Burilov, V. V. Skripacheva, A. R. Mustafina, S. E. Solovéva, A. I. Konovalov, Elektrokhimiya, 2009, 45, 840 [Russ. J. Electrochem. (Engl. Transl.), 2009, 45, 783].

    Google Scholar 

  53. A. Y. Ziganshina, S. V. Kharlamov, D. E. Korshin, R. K. Mukhitova, E. Kh. Kazakova, Sh. K. Latypov, V. V. Yanilkin, A. I. Konovalov, Tetrahedron Lett., 2008, 49, 5312.

    Article  CAS  Google Scholar 

  54. G. R. Nasybullina, V. V. Yanilkin, N. V. Nastapova, D. E. Korshin, A. Y. Ziganshina, A. I. Konovalov, J. Incl. Phen. Macrocycl. Chem., 2011, DOI: 10.1007/s10847-011-9975-9.

    Google Scholar 

  55. A. A. Karasik, R. N. Naumov, A. S. Balueva, Y. S. Spiridonova, O. N. Golodkov, H. V. Novikova, G. P. Belov, S. A. Katsyuba, E. E. Vandyukova, P. Lonnecke, E. Hey-Hawkins, O. G. Sinyashin, Heteroatom Chem., 2006, 17, 499.

    Article  CAS  Google Scholar 

  56. Z. Galus, Teoretyczne Podstawy Elektroanalizy Chemicznej, Panstwowe Wydawnictwo Naukowe, Warszawa, 1971.

    Google Scholar 

  57. A. J. Gordon, R. A. Ford, The Chemistś Companion, Wiley-Intersci. Publ., New York-London-Sydney-Toronto, 1972.

    Google Scholar 

  58. C. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, New York, 1970.

    Google Scholar 

  59. A. P. Tomilov, Yu. M. Kargin, I. N. Chernykh, Elektrokhimiya elementoorganicheskikh soedinenii (elementy IV, V i VI grupp periodicheskoi sistemy) [Electrochemistry of Organoelement Compounds (Elements of IV, V, and VI Groups of Mendeleevś Periodic Table)], Nauka, Moscow, 1986, 295 pp. (in Russian).

    Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    G. R. Nasybullina, V. V. Yanilkin, N. V. Nastapova, A. Yu. Ziganshina, D. E. Korshin, Yu. S. Spiridonova, A. A. Karasik & A. I. Konovalov

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  1. G. R. Nasybullina
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  2. V. V. Yanilkin
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  3. N. V. Nastapova
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Correspondence to V. V. Yanilkin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2274–2289, December, 2012.

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Nasybullina, G.R., Yanilkin, V.V., Nastapova, N.V. et al. Binding of 1,5-bis(p-sulfonatophenyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane with tetra(methyl viologen) calix[4]resorcinol. Russ Chem Bull 61, 2295–2310 (2012). https://doi.org/10.1007/s11172-012-0324-y

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