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. 2008 Nov 7;73(21):8553-7.
doi: 10.1021/jo801692v. Epub 2008 Oct 8.

Synthesis of a new family of hexakisferrocenyl hexagons and their electrochemical behavior

Koushik Ghosh  1 , Yue Zhao, Hai-Bo Yang, Brian H Northrop, Henry S White, Peter J Stang
Affiliations

Synthesis of a new family of hexakisferrocenyl hexagons and their electrochemical behavior

Koushik Ghosh et al. J Org Chem. .

Abstract

The design and synthesis of two new hexakisferrocenyl hexagons has been achieved via coordination-driven self-assembly wherein the size and relative distribution of six ferrocene moieties has been precisely controlled. Insight into the structure and electronic properties of these supramolecules was obtained through electrochemical studies.

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Figures

FIGURE 1
FIGURE 1
Schematic and molecular structure of 120° ferrocenyl donor 1 and acceptor 2.
FIGURE 2
FIGURE 2
The 31P NMR spectra of the ferrocenyl acceptor 2 (A) and hexakisferrocenyl hexagons 6 (B) and 8 (C).
FIGURE 3
FIGURE 3
Partial 1H NMR spectra of ferrocenyl acceptor 2 (A), ferrocenyl donor 1 (B), small hexakisferrocenyl hexagon 6 (C), linear donor 7 (D), and large hexakisferrocenyl hexagon 8 (E).
FIGURE 4
FIGURE 4
Molecular force field models of hexakisferrocenyl hexagons 6 (A) and 8 (B).
FIGURE 5
FIGURE 5
Cyclic voltammetric response on a Pt electrode (0.009 cm2) of 0.20 mM 6 (A) and 8 (B) at a scan rate of 25–250 mV/s. Steady-state response on a Pt nanodiskelectrode with radius of 30 nm at a scan rate of 20 mV/s for 0.20 mM 6 (C) and 0.20 mM 8 (D) in CH2Cl2 containing 0.15 M n-Bu4NPF6.
SCHEME 1
SCHEME 1
Synthesis of 120° Ferrocene Containing Di-Pt(II) Acceptor Subunit 2.
SCHEME 2
SCHEME 2
Self-assembly of Different Sized Hexakisferrocenyl Hexagons.
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References

    1. Haeckel E. Challenger Monograph. 1887
    1. Lamparth I, Herzog A, Hirsch A. Tetrahedron. 1996;52:5065.
    2. Kroto HW. Nature. 1985;318:162.
    3. Krätschmer W. Nature. 1991;265:54.
    4. Berresheim AJ, Müller M, Müllen K. Chem. Rev. 1999;99:1747. - PubMed
    5. Ajayan PM. Chem. Rev. 1999;99:1787. - PubMed
    1. Stang PJ, Olenyuk B. Acc. Chem. Res. 1997;30:502.
    2. Leininger S, Olenyuk B, Stang PJ. Chem. Rev. 2000;100:853. - PubMed
    3. Seidel SR, Stang PJ. Acc. Chem. Res. 2002;35:972. - PubMed
    4. Schwab PFH, Levin MD, Michl J. Chem. Rev. 1999;99:1863. - PubMed
    5. Gianneschi NC, Masar MS, III, Mirkin CA. Acc. Chem. Res. 2005;38:825. - PubMed
    6. Cotton FA, Lin C, Murillo CA. Acc. Chem. Res. 2001;34:759. - PubMed
    7. Fujita M, Tominaga M, Hori A, Therrien B. Acc. Chem. Res. 2005;38:369. - PubMed
    8. Fiedler D, Leung DH, Bergman RG, Raymond KN. Acc. Chem. Res. 2005;38:349. - PubMed
    9. Steel PJ. Acc. Chem. Res. 2005;38:243. - PubMed
    1. Stang PJ, Persky NE, Manna J. J. Am. Chem. Soc. 1997;119:4777.
    2. Hasenknopf B, Lehn J-M, Boumediene N, Dupont-Gervais A, van Dorsselaer A, Kneisel B, Fenske D. J. Am.Chem. Soc. 1997;119:10956.
    3. Tzeng BC, Lo WC, Che CM, Peng SM. J. Chem. Soc. Chem. Commun. 1996;181
    4. Mamula O, Zelewsky A, Bernardinelli G. Angew. Chem. Int. Ed. 1998;37:289. - PubMed
    5. Matsumoto N, Motoda Y, Matsuo T, Nakashima T, Re N, Dahan F, Tuchagues J-P. Inorg. Chem. 1999;38:1165. - PubMed
    6. Mingos DMP, Yau J, Menzer S, Williams DJ. Angew. Chem. Int. Ed. Engl. 1995;34:1894.
    1. Leininger S, Schmitz M, Stang PJ. Org. Lett. 1999;1:1921. - PubMed

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