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Gold-nanoparticle-cored Polyferrocenyl Dendrimers: Modes of Synthesis and Functions as Exoreceptors of Biologically Important Anions and Re-usable Redox Sensors

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Abstract

Polyamidoferrocenylalkylthiolate-Au nanoparticles (AuNP) and AuNP-cored polyferrocenyl dendrimers have been assembled either by the ligand-substitution method from dodecanethiolate-AuNP (AB3 units) or Brust-type direct synthesis from a 1-1 mixture of dodecanethiol and dendronized thiol (AB9 units). The AuNP-cored polyferrocenyl dendrimers are a new type of dendrimers with a AuNP core. AuNPs containing a nonasilylferrocenyl dendron have been synthesized; they bear respectively 180 and 360 ferrocenyl units at the periphery. These AuNPs selectively recognize the anions H2PO −4 and adenosine-5′-triphosphate (ATP2−) with a positive dendritic effect. Recognition is monitored by the appearance of a new wave at a less positive potential in cyclic voltammetry (CV). These AuNP-cored polyferrocenyl dendrimers can form robust modified electrodes that serve as re-usable sensors of ATP2− by simple washing with CH2Cl2.

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References

  • (a) F. Antonii, Panacea Aurea-Auro Potabile (Bibliopolio Frobeniano, Hamburg, 1618); (b) J. Kunckels, Nuetliche Observationes oder Anmerkungen von Auro und Argento Potabili (Schutzens, Hamburg, 1676); (c) H. H. Helcher, (J. Herbord Klossen, Breslau, Leipzig, 1718); (d) Dictionnaire de Chimie (Lacombe, Paris, 1769); (e) Mrs. Fulhame, An Essay on Combustion with a View to a New Art of Dying and Painting (J. Cooper, London, 1794); (f) W. Ostwald, Kolloid Zeitschrift 4, 5 (1909); (g) R. L. Kahn, in Colloid Chemistry, J. Alexander, ed. (The Chemical Catalog Co, New York, 1928) Vol. II, p. 757; (h) E. A. Hauser, J. Chem. Ed. 456 (1952); (i) G. Savage, Glass and Glassware (Octopus Book, London, 1975); (j) D. H. Brown and W. E. Smith, Chem. Soc. Rev. 9, 217 (1980); (k) in Virus Diagnosis and Research, A. D. Hyatt, B. T. Eaton, eds. (CRC Press, Boca Brota, FL, 1993); (l) T. Yonezawa and N. Toshima, in Advanced Functional Molecules and Polymers, H. S. Nalwa, ed. (OPA N.V., 2001), Vol. 2, Chap. 3, pp. 65–86; (m) for a brief review of historical, medicinal and decoration aspects of AuNPs, see ref. 8a.

  • T. Graham (1861) Phil. Trans. Roy. Soc. 151 183

    Google Scholar 

  • M. Faraday (1857) Phil. Trans. 147 145

    Google Scholar 

  • (a) G. Mie, Ann. Phys. 25, 377 (1908); (b) in Optical Properties of Metal Clusters, U. Freibig and M. Vollmer, eds. (Springer Verlag, New York, 1995); (c) A. P. Alivisatos, Science 271, 933 (1996).

  • J. J. Storhoff C. A. Mirkin (1999) Chem. Rev. 99 1849

    Google Scholar 

  • (a) M. A. Hayat, Colloidal Gold, Principles, Methods and Applications, (Academic Press, New York, 1989); (b) G. Schmid, Chem. Rev. 92, 1709 (1992); Clusters and Colloids, G. Schmid, ed. (VCH: Weinheim, 1994); (c) J. H. Fendler and F. C. Meldrum, Adv. Mater. 7, 607 (1995).

  • (a) D. Bethell, M. Brust, D. J. Schiffrin, and C. Kiely, J. Electroanal. Chem. 409, 137 (1996); (b) E. Matijevic, Curr. Opin. Coll. Interf. Sci. 1(2), 176 (1996); G. Schmid and L. F. Chi, Adv. Mater. 10(7), 515 (1998); G. Schmid, M. Bäumle, M. Geerkens, I. Heim, C. Osemann, and T. Sawitowski, Chem. Soc. Rev. 28, 179 (1999); (c) G. Schmid, in Nanoscale Materials in Chemistry, K. J. Klabunde, ed. (Wiley, New York, 2001); (d) A. S. Edelstein, R. C. Cammarata, Nanoparticle: Synthesis, Properties and Applications, (Institute of Physics Publishing, Bristol, 1996); and (e) in Metal Nanoparticles – Synthesis, Characterization and Applications. D. L. Feldheim and A. F. Colby Jr., eds. (Marcel Dekker, New York, 2002).

  • For a recent comprehensive reviews on AuNPs, see: (a) M.-C. Daniel and D. Astruc, Chem. Rev. 104, 293 (2004); (b) for a recent book on nanoparticles, see: G. Schmid, ed. Nanoparticles (Wiley-VCH, Weinheim, 2004).

  • (a) J. Turkevitch, P. C. Stevenson, and J. Hillier, Disc. Faraday Soc. 11, 55 (1951); (b) G. Frens, Nat. Phys. Sci. 241, 20 (1973). For a more recent report on citrate-stabilized AuNPs, see: (c) K. J. Watson, J. Zhu, SB. T. Nguyen, and C. A. Mirkin, J. Am. Chem. Soc. 121, 462 (1999).

  • (a) M. Giersig and P. Mulvaney, Langmuir 9, 3408 (1993); (b) T. Ung, L. M. Liz-Marzán, and P. Mulvaney, Coll. Surf. A: Physicochem. Eng. Asp. 202, 119 (2002).

  • (a) M. Brust, M. Walker, D. Bethell, D. J. Schiffrin, and R. J. Whyman, J. Chem. Soc. Chem. Commun. 801 (1994); (b) M. Brust, J. Fink, D. Bethell, D. J. Schiffrin, and C. J. Kiely, J. Chem. Soc., Chem. Commun. 1655 (1995); M. Brust and C. J. Kiely, Coll. Surf. A: Physicochem. Eng. Asp. 202, 175 (2002); (c) M. Hasan, D. Bethell, and M. Brust, J. Am. Chem. Soc. 1132 (2003).

  • (a) F. Moulines, L. Djakovitch, R. Boese, B. Gloaguen, W. Thiel, J.-L. Fillaut, M.-H. Delville, and D. Astruc, Angew. Chem. Int. Ed. Engl. 32, 1075 (1993); (b) C. Valério, J.-L. Fillaut, J. Ruiz, J. Guittard, J.-C. Blais,and D. Astruc, J. Am. Chem. Soc. 119, 2588 (1997); (c) C. Valério, E. Alonso, J. Ruiz, J.-C. Blais, and D. Astruc, Angew. Chem. Int. Ed. Engl. 38, 1747 (1999); (d) A. Labande and D. Astruc, Chem. Commun. 1007 (2000); (e) D. Astruc, Acc. Chem. Res. 33, 287 (2000); (f) M.-C. Daniel, J. Ruiz, S. Nlate, J. Palumbo, J.-C. Blais, and D. Astruc, Chem. Commun. 2000 (2001); (g) A. Labande, J. Ruiz, and D. Astruc, J. Am. Chem. Soc. 124, 1782 (2002); (h) D. Astruc, S. Nlate, and J. Ruiz, in Modern Arene Chemistry, D. Astruc, ed. (Wiley-VCH, Weinheim, 2002), pp. 400–434; (i) M.-C. Daniel, J. Ruiz, and D. Astruc, J. Am. Chem. Soc. 125, 1150 (2003); (j) M.-C. Daniel, J. Ruiz, J.-C. Blais, N. Daro, and D. Astruc, Chem. Eur. J. 9, 4371 (2003); (k) M.-C. Daniel, J. Ruiz, S. Nlate, J.-C. Blais, and D. Astruc, J. Am. Chem. Soc. 125, 2617, (2003); (l) D. Astruc, J.-C. Blais, and M.-C. Daniel, V. Martinez, S. Nlate, and J. Ruiz, in Marcomolecular Symposia, A. Abd-El-Aziz ed. (Wiley-VCH, 2003) 196(1), pp. 1–25; (m) M.-C. Daniel, J. Ruiz, and D. Astruc, Chem. Commun. 2637 (2004, Feature Article); (n) M.-C. Daniel, F. Ba, J. Ruiz, and D. Astruc, Inorg. Chem. 43, 8649 (2004).

  • D. Fitzmaurice S. N. Rao J. Preece J. F. Stoddart S. Wenger N. Zaccheroni (1999) Angew. Chem. Int. Ed. Engl. 38 1147

    Google Scholar 

  • S. Sampath O. Lev (1997) Adv. Mater. 9 410

    Google Scholar 

  • (a) A. K. Boal and V. M. Rotello, J. Am. Chem. Soc. 121, 4914 (1999); (b) A. K. Boal and V. M. Rotello, J. Am. Chem. Soc. 122, 734 (2000); (c) A. Niemz and V. M. Rotello, Acc. Chem. Res. 32, 44 (1999).

  • (a) J. J. Storhoff, R. Elghanian, R. C. Mucic, C. A. Mirkin, and R. L. Letsinger, J. Am. Chem. Soc. 120, 1959 (1998); (b) R. C. Mucic, J. J. Storhoff, C. A. Mirkin, and R. L. Letsinger, J. Am. Chem. Soc. 120, 12674 (1998); (c) R. Elghanian, J. J. Storhoff, R. C. Mucic, R. L. Letsinger, and C. A. Mirkin, Science 277, 1078 (1997).

  • W. Shenton D. A. Davis S. Mann (1999) Adv. Mater. 119 11132

    Google Scholar 

  • A. C. Templeton W. P. Wuelfing R. W. Murray (2000) Acc. Chem. Res. 33 27 Occurrence Handle10.1021/ar9602664

    Article  Google Scholar 

  • (a) J.-M. Lehn, Acc. Chem. Res. 11, 49 (1978); (b) F. Vögtle, H. Sieger, and W. M. Müller, Topics Curr. Chem. 35, 90 (1982); (c) A. Kumar, N. L. Arbott, E. Kim, A. Biebuyck, and G. M. Whitesides, Acc. Chem. Res. 28, 219 (1995); (d) P. D. Beer, Adv. Inorg. Chem. 39, 79 (1992); (e) P. D. Beer, J. Chem. Soc. Chem. Commun. 689 (1996); (f) P. D. Beer, Acc. Chem. Res. 31, 71 (1998); (g) P. D. Beer, P. A. Gale, and Z. Chen, Adv. Phys. Org. Chem. 31, 1 (1998); (h) P. D. Beer, Angew. Chem. Int. Ed. 40, 486 (2001); (i) J. H. R. Tucker and S. R. Collison, Chem. Soc. Rev. 31, 147 (2002); (j) P. D. Beer and E. J. Hayes, Coord. Chem. Rev. 240, 167 (2003).

  • (a) M. J. Hosteler, S. J. Green, J. J. Stockes, and R. W. Murray, J. Am. Chem. Soc. 118, 4212 (1996); (b) R. S. Ingram, M. J. Hostetler, and R. W. Murray, J. Am. Chem. Soc. 119, 9175 (1997); (c) M. J. Hostetler, A. C. Templeton, and R. W. Murray, Langmuir 15, 3782 (1999).

  • (a) T. Horikoshi, M. Itoh, M. Kurihara, K. Kubo, and H. J. Nishihara, Electroanal. Chem. 473, 113 (1999); (b) M. Yamada, T. Tadera, K. Kubo, and H. Nishihara, Langmuir 17, 2263 (2001); (c) M. Yamada, I. Quiros, J. Mizutani, K. Kubo, and H. Nishihara, Phys. Chem. Chem. Phys. 3, 3377 (2001); (d) Y. Men, K. Kubo, M. Kurihara, and H. Nishihara, Phys. Chem. Chem. Phys. 3, 3427 (2001).

  • D. Astruc, in Electron Transfer in Chemistry, V. Balzani ed. (Wiley-VCH, New York, 2001), Vol. 2, Organic, Inorganic and Organometallic Molecules, J. Mattay and D. Astruc, eds. section 2, Chapter 4, p. 728.

  • (a) C. B. Gorman, B. L. Parkhurst, W. Y. Su, and K.-Y. Chen, J. Am. Chem. Soc. 119, 1141 (1997); (b) C. B. Gorman, Adv. Mater. 9, 1117 (1997) and 10, 295 (1998); (c) C. B. Gorman, J. C. Smith, M. W. Hager, B. L. Parkhurst, H. Sierzputowska-Gracz, and C. A. Haney, J. Am. Chem. Soc. 121, 9958 (1999); (c) S. J. Green, J. J. Pietron, J. J. Stockes, M. J. Hosteler, H. Vu, W. P. Wuelfing, and R. W. Murray, Langmuir 14, 5612 (1998).

  • (a) A. E. Kaifer and M. Gomez-Kaifer, Supramolecular Electrochemistry (Wiley-VCH, Weinheim, 1999), Chapter 16, p. 207; (b) C. M. Cardona and A. E. Kaifer, J. Am. Chem. Soc. 120, 4023 (1998).

  • V. Sartor, L. Djakovitch, J.-L. Fillaut, F. Moulines, F. Neveu, V. Marvaud, J. Guittard, J.-C. Blais, and D. Astruc, J. Am. Chem. Soc. 121, 2929 (1999); V. Sartor, S. Nlate, L. Djakovitch, J.-L. Fillaut, F. Moulines, F. Neveu, V. Marvaud, J. Guittard, J.-C. Blais, and D. Astruc, New. J. Chem. 24, 351 (2000).

  • (a) S. W. Krsda and D. Seyferth, J. Am. Chem. Soc. 120, 3604 (1999); (b) P. Jutzi, C. Batz, B. Neumann and H. G. Stammler, Angew. Chem. Int. Ed. 35, 2118 (1996).

  • (a) A. J. Bard and L. R. Faulkner, Electrochemical Methods, (Wiley, New York, 1980); (b) J.-B. Flanagan, S. Margel, A. J. Bard, and F. C. Anson, J. Am. Chem. Soc. 100, 4248 (1978).

  • (a) D. Astruc, in Electron-Transfer and Radical Processes in Transition-Metal Chemistry (VCH, New York, 1995), Chapters 2 and 7; (b) the internal reference was decamethylferrocene, [FeCp*2], a much better reference than ferrocene (the E° values are then converted vs. [FeCp2], however): see ref. 22; (c) for strong and weak host–guest interaction and their electrochemical investigation from an analytical viewpont, see: S. R. Miller, D. A. Gustowski, Z.-H. Chen, G. W. Gokel, L. Echegoyen, and A. E. Kaifer, Anal. Chem. 60, 2021 (1988).

  • O. Reynes, J.-C. Moutet, J. Pecaut, G. Royal, and E. Saint-Aman, Chem. Eur. J. 6, 2544 (2000); O. Reynes, G. Royal, E. Chainet, J.-C. Moutet, and E. Saint-Aman, Electroanalysis 15, 65 (2002); O. Reynes, T. Gulon, J.-C. Moutet, G. Royal, and E. Saint-Aman, J. Organomet. Chem. 656, 116 (2002); O. Reynes, J.-C. Moutet, J. Pecaut, G. Royal, and E. Saint-Aman, New J. Chem. 26, 9 (2002).

  • Reviews on ferrocenyl dendrimers and their electrochemistry: (a) I. Cuadrado, M. Morán, C. M. Casado, B. Alonso, and J. Losada, Coord. Chem. Rev. 193–195, 395–445 (1999); (b) C. -M. Casado, I. Cuadrado, M. Morán, B. Alonso, B. Garcia, B. Gonzales, and J. Losada, Coord. Chem. Rev. 53, 185–186, (1999); (c) G. R. Newkome, C. N. Moorefield, and F. Vögtle, Dendrimers and Dendrons: Concepts, Syntheses, Applications (Wiley-VCH, Weinheim, 2001).

  • (a) Biferrocenyl-substituted thiol-nanoparticles deposited on metal surfaces: M. Yamada, I. Quiros, J. Mizutani, K. Kubo, and I. Nishihara, Phys. Chem. Chem. Phys. 3, 3377 (2001); (b) M. Yamada, A. Kuzume, M. Kurihara, K. Kubo, and H. Nishihara, Chem. Commun. 2476 (2001); (c) M. Yamada and H. Nishihara, Chem. Commun. 2578 (2002).

  • (a) L. Balogh and D. A. Tomalia, J. Am. Chem. Soc. 120, 7355 (1998); (b) M. Zhao and R. M. Crooks, Angew. Chem. Int. Ed. 38, 364 (1999); (c) Y. Niu, L. K. Yeung and R. M. Crooks, J. Am. Chem. Soc. 123, 6840 (2001); (c) R. M. Crooks, M. Zhao, L. Sun, V. Chechik, and L. K. Yeung, Acc. Chem. Res. 34, 181 (2001).

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  1. Contribution from the Groupe Nanoscience et Catalyse, LCOO, UMR CNRS N °5802, Université Bordeaux I, 33405, Talence, Cedex, France

    Marie-Christine Daniel, Jaime Ruiz Aranzaes, Sylvain Nlate & Didier Astruc

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  1. Marie-Christine Daniel
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Daniel, MC., Aranzaes, J.R., Nlate, S. et al. Gold-nanoparticle-cored Polyferrocenyl Dendrimers: Modes of Synthesis and Functions as Exoreceptors of Biologically Important Anions and Re-usable Redox Sensors. J Inorg Organomet Polym 15, 107–119 (2005). https://doi.org/10.1007/s10904-004-2381-7

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