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Dendritic Molecular Nanobatteries and the Contribution of Click Chemistry

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Abstract

This article is a mini-review mostly based on the work of the authors’ laboratory on the redox chemistry of metallodendrimers and gold nanoparticles, with emphasis on “click” chemistry. Late transition-metal sandwich complexes possess a rather unique ability to withstand two or three oxidation states without breakdown, especially with permethylated π-cyclopentadienyl or arene ligands. When they are linked to dendritic cores, the assembled nano-systems undergo chemically and electrochemically reversible transfer of a large number of electrons (up to 14,000). These multiple redox processes are useful for nanodevices behaving as nanobatteries for redox sensing, modified electrode surfaces and redox catalysis. Click chemistry was recently disclosed as one of the most powerful means to form such assemblies including both arene-cored and gold nanoparticle-cored dendrimers.

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References

  1. F.A. Cotton, G. Wilkinson, C.A. Murillo, M. Bochman, Advanced Inorganic Chemistry, 6th edn. (Wiley Interscience, New York, 1999)

    Google Scholar 

  2. A.S. Arico, P. Bruce, B. Scrosati, J.-M. Tarascon, W. Van Schalkwijk, Nat. Mater. 4, 366–377 (2005)

    Article  CAS  Google Scholar 

  3. I. Bertini, H.B. Gray, S.J. Lippard, J.S. Valentine, Bioinorganic Chemistry (University Science Books, Mill Valley, 1994)

    Google Scholar 

  4. D. Astruc. Electron Transfer and Radical Processes in Transition Metal Chemistry (Wiley–VCH, New York, 1995). See also the detailed foreword by H. Taube therein

  5. D. Astruc, Nat. Chem. 4, 255–267 (2012)

    Article  CAS  Google Scholar 

  6. K.M. Kadish, K.M. Smith, R. Guilard (eds.), Handbook of Porphyrin Science, Vol 1–25 (World Scientific Publishing, Singapore, 2010–2012)

  7. T.P. Fehlner, J.-F. Halet, J.-Y. Saillard, Molecular Clusters (Cambridge University Press, Cambridge, 2007)

    Book  Google Scholar 

  8. D. Astruc, Organometallic Chemistry and Catalysis Chap. 11 (Springer, Heidelberg, 2007)

  9. Electron Transfer in Chemistry, Vol. 1–4, ed. by V. Balzani. (Wiley–VCH, Weinheim, 2001)

  10. N.G. Connelly, W.E. Geiger, Adv. Organomet. Chem. 23, 1–93 (1984)

    Article  CAS  Google Scholar 

  11. W.E. Geiger, N.G. Connelly, Adv. Organomet. Chem. 24, 87–130 (1985)

    Article  CAS  Google Scholar 

  12. W.E. Geiger, J. Organomet. Chem. Libr. 23, 142–172 (1990)

    Google Scholar 

  13. N.G. Connelly, W.E. Geiger, Chem. Rev. 96, 877–910 (1996)

    Article  CAS  Google Scholar 

  14. W.E. Geiger, Organometallics 26, 5738–5765 (2007)

  15. P.D. Beer, P.A. Gale, Angew. Chem. Int. Ed. 40, 486–416 (2001)

    Google Scholar 

  16. O. Reynes, J.-C. Moutet, J. Pecaut, G. Royal, E. Saint-Aman, New J. Chem. 26, 9–12 (2002)

    Article  CAS  Google Scholar 

  17. M.P.G. Armada, J. Losada, M. Zamora, B. Alonso, I. Cuadrado, C.M. Casado, Bioelectrochem. 69, 65–73 (2006)

    Article  CAS  Google Scholar 

  18. F.J. Martinez, B. Gonzales, B. Alonso, J. Losada, M.P. Garcia-Armada, C. Casado, J. Inorg. Chem. Polym. Mater. 18, 51–58 (2008)

    CAS  Google Scholar 

  19. D. Astruc, M.-C. Daniel, J. Ruiz, Chem. Commun. 2637–2649 (2004)

  20. R.A. Sheldon, J.K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds (Academic Press, New York, 1981)

    Google Scholar 

  21. J.-M. Savéant, Acc. Chem. Res. 13, 323–329 (1980)

    Article  Google Scholar 

  22. E. Steckhan, Angew. Chem. Int. Ed. Engl. 25, 683 (1986)

    Google Scholar 

  23. A.E. Shilov, Russ. Chem. Rev. 43, 378–398 (1974)

    Article  Google Scholar 

  24. G. Wilkinson, M. Rosenblum, M.C. Whittig, R.B. Woodward, J. Am. Chem. Soc. 74, 2125–2126 (1952)

    Article  CAS  Google Scholar 

  25. G. Wilkinson, P.L. Pauson, F.A. Cotton, J. Am. Chem. Soc. 76, 1970–1974 (1954)

    Article  CAS  Google Scholar 

  26. R.B. King, Organometallic Syntheses, vol 1 (Academic Press, New York, 1965)

  27. U. Kölle, F. Khouzami, Angew. Chem. Int. Ed. Engl. 19, 640–641 (1980)

    Google Scholar 

  28. J. Ruiz, D. Astruc, C.R. Acad, Sci. Ser. IIc Chim. 1, 21–27 (1998)

    CAS  Google Scholar 

  29. I. Noviandry, K.N. Brown, D.S. Fleming, P.T. Gulyas, P.A. Lay, A.F. Masters, L.J. Phillips, J. Phys. Chem. B. 103, 6713–6722 (1999)

    Article  Google Scholar 

  30. J.-R. Hamon, D. Astruc, P. Michaud, J. Am. Chem. Soc. 103, 758–766 (1981)

    Article  CAS  Google Scholar 

  31. M. Lacoste, F. Varret, L. Toupet, D. Astruc, J. Am. Chem. Soc. 109, 6504–6506 (1987)

    Article  CAS  Google Scholar 

  32. M.H. Desbois, D. Astruc, J. Guillin, F. Varret, J. Am. Chem. Soc. 111, 5800–5809 (1989)

    Article  CAS  Google Scholar 

  33. C. Moinet, E. Roman, D. Astruc, J. Electroanal. Chem. 121, 241–253 (1981)

    Article  CAS  Google Scholar 

  34. S. Rigaut, M.-H. Delville, J. Losada, D. Astruc, Inorg. Chim. Acta. 334, 225–242 (2002)

    Article  CAS  Google Scholar 

  35. J. Ruiz, M. Lacoste, D. Astruc, J. Am. Chem. Soc. 112, 5471–5483 (1990)

    Article  CAS  Google Scholar 

  36. D.S. Brown, M.-H. Delville, R. Boese, K.P.C. Vollhardt, D. Astruc, Angew. Chem. Int. Ed. Engl. 33, 661–663 (1994)

    Google Scholar 

  37. E. Alonso, D. Astruc, J. Am. Chem. Soc. 122, 3222–3223 (2000)

    Article  CAS  Google Scholar 

  38. J.C. Green, M.R. Kelly, M.C. Payne, E.A. Seddon, D. Astruc, J.-R. Hamon, P. Michaud, Organometallics. 2, 211–218 (1983)

    Article  CAS  Google Scholar 

  39. A. Madonik, D. Astruc, J. Am. Chem. Soc. 106, 2437–2439 (1984)

    Article  CAS  Google Scholar 

  40. A.N. Nesmeyanov, Adv. Organomet. Chem. 10, 1 (1972)

    Article  CAS  Google Scholar 

  41. R.G. Sutherland, S.C. Chen, W.J. Pannekoek, C.C. Lee, Ann. N. Y. Acad. Sci. 295, 192–200 (1977)

    Article  CAS  Google Scholar 

  42. J. Ruiz, F. Ogliaro, J.-Y. Saillard, J.-F. Halet, F. Varret, D. Astruc, J. Am. Chem. Soc. 120, 11693–11705 (1998)

    Article  CAS  Google Scholar 

  43. G.R. Newkome, C.N. Moorefield, F. Vögtle, Dendrimers and Dendrons, Syntheses, Concepts, Applications (Wiley–VCH, Weinheim, 2001)

    Google Scholar 

  44. G.R. Newkome, C.N. Moorefield, Chem. Rev. 99, 1689–1746 (1999)

    Article  CAS  Google Scholar 

  45. G.R. Newkome, C. Shreiner, Chem. Rev. 110, 6338–6442 (2010)

    Article  CAS  Google Scholar 

  46. S.H. Hwang, C.D. Shreiner, C.N. Moorefield, G.R. Newkome, New J. Chem. 31, 1192–1217 (2007)

    Article  CAS  Google Scholar 

  47. C.M. Casado, I. Cuadrado, M. Moran, B. Alonso, B. Garcia, B. Gonzales, J. Losada, Coord. Chem. Rev. 185–6, 53–79 (1999)

    Article  Google Scholar 

  48. J. Ruiz, G. Lafuente, S. Marcen, C. Ornelas, S. Lazare, E. Cloutet, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 7250–7257 (2003)

    Article  CAS  Google Scholar 

  49. C. Ornelas, J. Ruiz, C. Belin, D. Astruc, J. Am. Chem. Soc. 131, 590–601 (2009)

    Article  CAS  Google Scholar 

  50. C. Valério, J.-L. Fillaut, J. Ruiz, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 119, 2588–2589 (1997)

    Article  Google Scholar 

  51. C. Ornelas, J. Ruiz, D. Astruc, Organometallics. 28, 4431–4437 (2009)

    Article  CAS  Google Scholar 

  52. D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev. 110, 1857–1959 (2010)

    Article  CAS  Google Scholar 

  53. G.R. Newkome, Z. Yao, G.R. Baker, V.K. Gupta, J. Org. Chem. 50, 1857–1859 (1985)

    Google Scholar 

  54. C. Ornelas, D. Méry, E. Cloutet, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 130, 1495–1506 (2008)

    Article  CAS  Google Scholar 

  55. T. Kusamoto, J. Ruiz, D. Astruc, New J. Chem. 33, 2204–2209 (2009)

    Article  CAS  Google Scholar 

  56. C. Ornelas, J. Ruiz, D. Astruc, Organometallics. 28, 2716–2723 (2009)

    Article  CAS  Google Scholar 

  57. R. Djeda, C. Ornelas, J. Ruiz, D. Astruc, Inorg. Chem. 49, 6085–6101 (2010)

    Article  CAS  Google Scholar 

  58. H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004–2021 (2001)

    Google Scholar 

  59. D. Astruc, F. Chardac, Chem. Rev. 101, 2991–3031 (2001)

    Article  CAS  Google Scholar 

  60. G. Franc, A. Kakkar, Chem. Commun. 5267–5276 (2008)

  61. V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596–2599 (2002)

    Google Scholar 

  62. M. Meldal, C.W. Tornøe, C. Christensen, J. Org. Chem. 67, 3057–3064 (2002)

    Article  Google Scholar 

  63. M. Meldal, C.W. Tornøe, Chem. Rev. 108, 2952–3015 (2008)

    Article  CAS  Google Scholar 

  64. P.L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 39, 1338–1354 (2010)

    Article  CAS  Google Scholar 

  65. J.E. Hein, V.V. Fokin, Chem. Soc. Rev. 39, 1300–1315 (2010)

    Article  Google Scholar 

  66. L. Liang, D. Astruc, Coord. Chem. Rev. 255, 2933–2945 (2011)

    Article  CAS  Google Scholar 

  67. C. Ornelas, J. Ruiz, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. 46, 872–877 (2007)

    Google Scholar 

  68. C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Chem. Eur. J. 14, 50–64 (2008)

    Article  CAS  Google Scholar 

  69. J. Camponovo, J. Ruiz, E. Cloutet, D. Astruc, Chem. Eur. J. 15, 2990–3002 (2009)

    Article  CAS  Google Scholar 

  70. R. Djeda, A. Rapakousiou, L. Liang, N. Guidolin, J. Ruiz, D. Astruc, Angew. Chem. Int. Ed. 49, 8152–8156 (2010)

    Google Scholar 

  71. J.B. Flanagan, A. Marcel, A.J. Bard, F.C. Anson, J. Am. Chem. Soc. 100, 4258–4253 (1978)

    Google Scholar 

  72. D.E. Richardson, H. Taube, Coord. Chem. Rev. 60, 107–129 (1984)

    Article  CAS  Google Scholar 

  73. F. Barrière, W.E. Geiger, Acc. Chem. Res. 43, 1030–1039 (2010)

    Article  Google Scholar 

  74. A.K. Diallo, J.-C. Daran, F. Varret, J. Ruiz, D. Astruc, Angew. Chem. Int. Ed. 48, 3141–3145 (2009)

    Google Scholar 

  75. A.K. Diallo, C. Absalon, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 133, 629–641 (2011)

    Article  CAS  Google Scholar 

  76. A. Labande, D. Astruc, Chem. Commun. 1007–1008 (2000)

  77. A. Labande, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 124, 1782–1789 (2002)

    Article  CAS  Google Scholar 

  78. M.-C. Daniel, J. Ruiz, S. Nlate, J. Palumbo, J.-C. Blais, D. Astruc, Chem. Commun. 2000–2001 (2001)

  79. M.-C. Daniel, J. Ruiz, S. Nlate, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 2617–2628 (2003)

    Article  CAS  Google Scholar 

  80. N. Candelon, D. Lastécouères, A.K. Diallo, J. Ruiz, D. Astruc, J.-M. Vincent, Chem. Commun. 741–743 (2008)

  81. L. Liang, J. Ruiz, D. Astruc, Adv. Syn. Catal. 353, 3434–3450 (2011)

    Article  CAS  Google Scholar 

  82. A. François, A. Laroche, N. Pinaud, L. Salmon, J. Ruiz, J. Robert, D. Astruc, ChemMedChem. 6, 2003–2008 (2011)

    Article  Google Scholar 

  83. P. Zhao, M. Grillaud, L. Salmon, J. Ruiz, D. Astruc, Adv. Syn. Catal. 354, 1001–1011 (2012)

    Article  CAS  Google Scholar 

  84. D. Astruc, L. Liang, A. Rapakousiou, J. Ruiz, Acc. Chem. Res. 45, 630–640 (2012)

    Article  CAS  Google Scholar 

  85. Frontiers in Transition-Metal Containing Polymers, ed. by A.S. Abd-El-Aziz, I. Manners (Wiley, New York, 2007)

  86. I. Manners, Science. 294, 1664–1666 (2001)

    Article  CAS  Google Scholar 

  87. D. Herbert, U.F. Mayer, I. Manners, Angew. Chem. Int. Ed. 46, 5060–5081 (2007)

    Google Scholar 

  88. A.S. Abd-El-Aziz, S. Bernardin, Coord. Chem. Rev. 203, 219–267 (2000)

    Article  CAS  Google Scholar 

  89. B. Helms, J.M.J. Fréchet, Adv. Syn. Catal. 348, 1125–1148 (2006)

    Article  CAS  Google Scholar 

  90. D. Astruc, K. Heuze, S. Gatard, D. Méry, S. Nlate, L. Plault, Adv. Syn. Catal. 347, 329–338 (2005)

    Article  CAS  Google Scholar 

  91. C. Ornelas, J. Ruiz, L. Salmon, D. Astruc, Adv. Syn. Catal. 350, 837–845 (2008)

    Article  CAS  Google Scholar 

  92. Y. Ochi, M. Suzuki, T. Imaoka, H. Nishihara, Y. Einaga, K. Yamamoto, J. Am. Chem. Soc. 132, 5061–5069 (2010)

    Article  CAS  Google Scholar 

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Acknowledgement

Invaluable contributions and discussions with Drs Azzedine Bousseksou, Lionel Salmon and Jean-Claude Daran (LCC, Toulouse), Prof. Jean-Yves Saillard, Drs Samia Kahlal and Christiane Perrin (Rennes), and Prof François Varret (Versailles), concerning the subject of this mini-review during the last decade, and financial support from the University Bordeaux 1, the Centre National de la Recherche Scientifique (CNRS), the Institut Universitaire de France (IUF), the Agence Nationale pour la Recherche (ANR, PhD grants to LL and AD), the China Scholarship Council (CSC) from the People’s Republic of China (PhD grant to PZ), the Fundaçao para a Ciencia e a Technologia, Portugal (PhD grant to CO), and the Ministère de l’Enseignement Supérieur de la Côte d’Ivoire (PhD grant to RD) are gratefully acknowledged.

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  1. ISM, UMR CNRS N° 5255, University Bordeaux, 351 Cours de la Libération, 33405, Talence Cedex, France

    Didier Astruc, Pengxiang Zhao, Liyuan Liang, Amalia Rapakousiou, Rodrigue Djeda, Abdou Diallo, Tetsuro Kusamoto, Jaime Ruiz & Catia Ornelas

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  1. Didier Astruc
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  2. Pengxiang Zhao
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  3. Liyuan Liang
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  4. Amalia Rapakousiou
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Correspondence to Didier Astruc.

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This mini-review article is dedicated to our distinguished friend Professor Hiroshi Nishihara, a gentleman and superb scientist and teacher.

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Astruc, D., Zhao, P., Liang, L. et al. Dendritic Molecular Nanobatteries and the Contribution of Click Chemistry. J Inorg Organomet Polym 23, 41–49 (2013). https://doi.org/10.1007/s10904-012-9720-x

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