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.
Similar content being viewed by others
References
F.A. Cotton, G. Wilkinson, C.A. Murillo, M. Bochman, Advanced Inorganic Chemistry, 6th edn. (Wiley Interscience, New York, 1999)
A.S. Arico, P. Bruce, B. Scrosati, J.-M. Tarascon, W. Van Schalkwijk, Nat. Mater. 4, 366–377 (2005)
I. Bertini, H.B. Gray, S.J. Lippard, J.S. Valentine, Bioinorganic Chemistry (University Science Books, Mill Valley, 1994)
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
D. Astruc, Nat. Chem. 4, 255–267 (2012)
K.M. Kadish, K.M. Smith, R. Guilard (eds.), Handbook of Porphyrin Science, Vol 1–25 (World Scientific Publishing, Singapore, 2010–2012)
T.P. Fehlner, J.-F. Halet, J.-Y. Saillard, Molecular Clusters (Cambridge University Press, Cambridge, 2007)
D. Astruc, Organometallic Chemistry and Catalysis Chap. 11 (Springer, Heidelberg, 2007)
Electron Transfer in Chemistry, Vol. 1–4, ed. by V. Balzani. (Wiley–VCH, Weinheim, 2001)
N.G. Connelly, W.E. Geiger, Adv. Organomet. Chem. 23, 1–93 (1984)
W.E. Geiger, N.G. Connelly, Adv. Organomet. Chem. 24, 87–130 (1985)
W.E. Geiger, J. Organomet. Chem. Libr. 23, 142–172 (1990)
N.G. Connelly, W.E. Geiger, Chem. Rev. 96, 877–910 (1996)
W.E. Geiger, Organometallics 26, 5738–5765 (2007)
P.D. Beer, P.A. Gale, Angew. Chem. Int. Ed. 40, 486–416 (2001)
O. Reynes, J.-C. Moutet, J. Pecaut, G. Royal, E. Saint-Aman, New J. Chem. 26, 9–12 (2002)
M.P.G. Armada, J. Losada, M. Zamora, B. Alonso, I. Cuadrado, C.M. Casado, Bioelectrochem. 69, 65–73 (2006)
F.J. Martinez, B. Gonzales, B. Alonso, J. Losada, M.P. Garcia-Armada, C. Casado, J. Inorg. Chem. Polym. Mater. 18, 51–58 (2008)
D. Astruc, M.-C. Daniel, J. Ruiz, Chem. Commun. 2637–2649 (2004)
R.A. Sheldon, J.K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds (Academic Press, New York, 1981)
J.-M. Savéant, Acc. Chem. Res. 13, 323–329 (1980)
E. Steckhan, Angew. Chem. Int. Ed. Engl. 25, 683 (1986)
A.E. Shilov, Russ. Chem. Rev. 43, 378–398 (1974)
G. Wilkinson, M. Rosenblum, M.C. Whittig, R.B. Woodward, J. Am. Chem. Soc. 74, 2125–2126 (1952)
G. Wilkinson, P.L. Pauson, F.A. Cotton, J. Am. Chem. Soc. 76, 1970–1974 (1954)
R.B. King, Organometallic Syntheses, vol 1 (Academic Press, New York, 1965)
U. Kölle, F. Khouzami, Angew. Chem. Int. Ed. Engl. 19, 640–641 (1980)
J. Ruiz, D. Astruc, C.R. Acad, Sci. Ser. IIc Chim. 1, 21–27 (1998)
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)
J.-R. Hamon, D. Astruc, P. Michaud, J. Am. Chem. Soc. 103, 758–766 (1981)
M. Lacoste, F. Varret, L. Toupet, D. Astruc, J. Am. Chem. Soc. 109, 6504–6506 (1987)
M.H. Desbois, D. Astruc, J. Guillin, F. Varret, J. Am. Chem. Soc. 111, 5800–5809 (1989)
C. Moinet, E. Roman, D. Astruc, J. Electroanal. Chem. 121, 241–253 (1981)
S. Rigaut, M.-H. Delville, J. Losada, D. Astruc, Inorg. Chim. Acta. 334, 225–242 (2002)
J. Ruiz, M. Lacoste, D. Astruc, J. Am. Chem. Soc. 112, 5471–5483 (1990)
D.S. Brown, M.-H. Delville, R. Boese, K.P.C. Vollhardt, D. Astruc, Angew. Chem. Int. Ed. Engl. 33, 661–663 (1994)
E. Alonso, D. Astruc, J. Am. Chem. Soc. 122, 3222–3223 (2000)
J.C. Green, M.R. Kelly, M.C. Payne, E.A. Seddon, D. Astruc, J.-R. Hamon, P. Michaud, Organometallics. 2, 211–218 (1983)
A. Madonik, D. Astruc, J. Am. Chem. Soc. 106, 2437–2439 (1984)
A.N. Nesmeyanov, Adv. Organomet. Chem. 10, 1 (1972)
R.G. Sutherland, S.C. Chen, W.J. Pannekoek, C.C. Lee, Ann. N. Y. Acad. Sci. 295, 192–200 (1977)
J. Ruiz, F. Ogliaro, J.-Y. Saillard, J.-F. Halet, F. Varret, D. Astruc, J. Am. Chem. Soc. 120, 11693–11705 (1998)
G.R. Newkome, C.N. Moorefield, F. Vögtle, Dendrimers and Dendrons, Syntheses, Concepts, Applications (Wiley–VCH, Weinheim, 2001)
G.R. Newkome, C.N. Moorefield, Chem. Rev. 99, 1689–1746 (1999)
G.R. Newkome, C. Shreiner, Chem. Rev. 110, 6338–6442 (2010)
S.H. Hwang, C.D. Shreiner, C.N. Moorefield, G.R. Newkome, New J. Chem. 31, 1192–1217 (2007)
C.M. Casado, I. Cuadrado, M. Moran, B. Alonso, B. Garcia, B. Gonzales, J. Losada, Coord. Chem. Rev. 185–6, 53–79 (1999)
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)
C. Ornelas, J. Ruiz, C. Belin, D. Astruc, J. Am. Chem. Soc. 131, 590–601 (2009)
C. Valério, J.-L. Fillaut, J. Ruiz, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 119, 2588–2589 (1997)
C. Ornelas, J. Ruiz, D. Astruc, Organometallics. 28, 4431–4437 (2009)
D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev. 110, 1857–1959 (2010)
G.R. Newkome, Z. Yao, G.R. Baker, V.K. Gupta, J. Org. Chem. 50, 1857–1859 (1985)
C. Ornelas, D. Méry, E. Cloutet, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 130, 1495–1506 (2008)
T. Kusamoto, J. Ruiz, D. Astruc, New J. Chem. 33, 2204–2209 (2009)
C. Ornelas, J. Ruiz, D. Astruc, Organometallics. 28, 2716–2723 (2009)
R. Djeda, C. Ornelas, J. Ruiz, D. Astruc, Inorg. Chem. 49, 6085–6101 (2010)
H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004–2021 (2001)
D. Astruc, F. Chardac, Chem. Rev. 101, 2991–3031 (2001)
G. Franc, A. Kakkar, Chem. Commun. 5267–5276 (2008)
V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596–2599 (2002)
M. Meldal, C.W. Tornøe, C. Christensen, J. Org. Chem. 67, 3057–3064 (2002)
M. Meldal, C.W. Tornøe, Chem. Rev. 108, 2952–3015 (2008)
P.L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 39, 1338–1354 (2010)
J.E. Hein, V.V. Fokin, Chem. Soc. Rev. 39, 1300–1315 (2010)
L. Liang, D. Astruc, Coord. Chem. Rev. 255, 2933–2945 (2011)
C. Ornelas, J. Ruiz, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. 46, 872–877 (2007)
C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Chem. Eur. J. 14, 50–64 (2008)
J. Camponovo, J. Ruiz, E. Cloutet, D. Astruc, Chem. Eur. J. 15, 2990–3002 (2009)
R. Djeda, A. Rapakousiou, L. Liang, N. Guidolin, J. Ruiz, D. Astruc, Angew. Chem. Int. Ed. 49, 8152–8156 (2010)
J.B. Flanagan, A. Marcel, A.J. Bard, F.C. Anson, J. Am. Chem. Soc. 100, 4258–4253 (1978)
D.E. Richardson, H. Taube, Coord. Chem. Rev. 60, 107–129 (1984)
F. Barrière, W.E. Geiger, Acc. Chem. Res. 43, 1030–1039 (2010)
A.K. Diallo, J.-C. Daran, F. Varret, J. Ruiz, D. Astruc, Angew. Chem. Int. Ed. 48, 3141–3145 (2009)
A.K. Diallo, C. Absalon, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 133, 629–641 (2011)
A. Labande, D. Astruc, Chem. Commun. 1007–1008 (2000)
A. Labande, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 124, 1782–1789 (2002)
M.-C. Daniel, J. Ruiz, S. Nlate, J. Palumbo, J.-C. Blais, D. Astruc, Chem. Commun. 2000–2001 (2001)
M.-C. Daniel, J. Ruiz, S. Nlate, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 125, 2617–2628 (2003)
N. Candelon, D. Lastécouères, A.K. Diallo, J. Ruiz, D. Astruc, J.-M. Vincent, Chem. Commun. 741–743 (2008)
L. Liang, J. Ruiz, D. Astruc, Adv. Syn. Catal. 353, 3434–3450 (2011)
A. François, A. Laroche, N. Pinaud, L. Salmon, J. Ruiz, J. Robert, D. Astruc, ChemMedChem. 6, 2003–2008 (2011)
P. Zhao, M. Grillaud, L. Salmon, J. Ruiz, D. Astruc, Adv. Syn. Catal. 354, 1001–1011 (2012)
D. Astruc, L. Liang, A. Rapakousiou, J. Ruiz, Acc. Chem. Res. 45, 630–640 (2012)
Frontiers in Transition-Metal Containing Polymers, ed. by A.S. Abd-El-Aziz, I. Manners (Wiley, New York, 2007)
I. Manners, Science. 294, 1664–1666 (2001)
D. Herbert, U.F. Mayer, I. Manners, Angew. Chem. Int. Ed. 46, 5060–5081 (2007)
A.S. Abd-El-Aziz, S. Bernardin, Coord. Chem. Rev. 203, 219–267 (2000)
B. Helms, J.M.J. Fréchet, Adv. Syn. Catal. 348, 1125–1148 (2006)
D. Astruc, K. Heuze, S. Gatard, D. Méry, S. Nlate, L. Plault, Adv. Syn. Catal. 347, 329–338 (2005)
C. Ornelas, J. Ruiz, L. Salmon, D. Astruc, Adv. Syn. Catal. 350, 837–845 (2008)
Y. Ochi, M. Suzuki, T. Imaoka, H. Nishihara, Y. Einaga, K. Yamamoto, J. Am. Chem. Soc. 132, 5061–5069 (2010)
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.
Author information
Authors and Affiliations
Corresponding author
Additional information
This mini-review article is dedicated to our distinguished friend Professor Hiroshi Nishihara, a gentleman and superb scientist and teacher.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10904-012-9720-x