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Volumn 14, Issue 36, 2008, Pages 11610-11622

Light-driven rotary molecular motors on gold nanoparticles

Author keywords

Circular dichroism; Molecular devices; Nanostructures; Nanotechnology; Photochemistry

Indexed keywords

DICHROISM; GOLD; GRAFTING (CHEMICAL); HYDROCARBONS; LINEAR MOTORS; MOTORS; NANOSTRUCTURES; NANOTECHNOLOGY; NUCLEAR MAGNETIC RESONANCE; OLEFINS; OPTICAL PROPERTIES;

EID: 57649224052     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800814     Document Type: Article
Times cited : (45)

References (110)
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    • Three-dimensional models for 3 through its rotary cycle can be found in ref. [6].
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    • The Barton-Kellogg reaction was first developed by Staudinger and Siegwart: a) H. Staudinger, J. Siegwart, Helv. Chim. Ada 1920, 3, 833. The reaction was later explored by A. Schönberg et al.; for leading references see:
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    • This compound has been reported in the literature, but no experimental details were provided: P. Grammaticakis, Bull. Soc. Chim. Fr. 1964, 924.
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    • Disulfides 17 and 25 were prepared by a procedure of N. A. Noureldin, M. Caldwell, J. Hendry, D. G. Lee, Synthesis 1998, 1587.
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    • Disulfide 17 has been reported previously: L. Gattermann, Ber. Dtsch. Chem. Ges. 1899, 32, 1136.
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    • For leading references on this procedure, see: a) J. M. Fu, B. P. Zhao, M. J. Sharp, V. Snieckus, J. Org. Chem. 1991, 56, 1683;
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    • This diazo compound is unstable and begins to undergo side reactions upon warming to room temperature.
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    • 13C NMR spectroscopic data: R. S. E. Conn, A. V. Lovell, S. Karaday, L. M. Weinstock, J. Org. Chem. 1986, 51, 4710.
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    • This method necessitated the use of such an apolar eluent (heptane :iPrOH 98:2) that the low solubility of 35 rendered this approach prohibitively time consuming and wasteful of solvent
    • This method necessitated the use of such an apolar eluent (heptane :iPrOH 98:2) that the low solubility of 35 rendered this approach prohibitively time consuming and wasteful of solvent.
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    • This assignment is based on the position of the acetyl moiety relative to the naphthalene moiety in the upper half
    • This assignment is based on the position of the acetyl moiety relative to the naphthalene moiety in the upper half.
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    • -1). The elution times of the enantiomers were 12.7/14.9 min.
    • -1). The elution times of the enantiomers were 12.7/14.9 min.
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    • The relatively low solubility of 39 in common organic solvents made it hard to purify.
    • The relatively low solubility of 39 in common organic solvents made it hard to purify.
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    • For the sake of clarity, only one motor is depicted, whereas TEM and DLS data suggest the presence of an average of 26 motors per nanoparticle.
    • For the sake of clarity, only one motor is depicted, whereas TEM and DLS data suggest the presence of an average of 26 motors per nanoparticle.
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    • The absorption of gold is quite sensitive to its environment: K. Watanabe, D. Menzel, N. Nilius, H.-J. Freund, Chem. Rev. 2006, 106, 4301.
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    • Preparative HPLC was still required to access preparative amounts of diastereomerically pure material
    • Preparative HPLC was still required to access preparative amounts of diastereomerically pure material.
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    • Protons on the aromatic lower half positioned on the same side as the naphthalene moiety are shielded and their signals are shifted up-field
    • Protons on the aromatic lower half positioned on the same side as the naphthalene moiety are shielded and their signals are shifted up-field.
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    • 3 in DMF with 8-bromooctan-1-ol or 8-iodooctan-1-ol. Amine bases such as diisopropylethylamine were also employed to no apparent advantage.
    • 3 in DMF with 8-bromooctan-1-ol or 8-iodooctan-1-ol. Amine bases such as diisopropylethylamine were also employed to no apparent advantage.
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    • 13CN and 7-bromooctan-1-ol in five steps. See Supporting Information for synthetic procedures.
    • 13CN and 7-bromooctan-1-ol in five steps. See Supporting Information for synthetic procedures.
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    • 1HNMR spectra of the precursor. These intermediates were surprisingly sensitive to light.
    • 1HNMR spectra of the precursor. These intermediates were surprisingly sensitive to light.
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    • The iodide was used here because it led to a much cleaner and faster reaction
    • The iodide was used here because it led to a much cleaner and faster reaction.
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    • When sodium methoxide was used in distilled, degassed methanol, it was found that ca. 10 % had nevertheless been oxidized to the disulfide. No disulfide was observed when the ammonia solution was used.
    • When sodium methoxide was used in distilled, degassed methanol, it was found that ca. 10 % had nevertheless been oxidized to the disulfide. No disulfide was observed when the ammonia solution was used.
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    • 2) = 0.0863, R(F) = 0.0420, GoF = 1.036. CCDC-693600 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
    • 2) = 0.0863, R(F) = 0.0420, GoF = 1.036. CCDC-693600 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • This is the first example described in the literature in which the absolute configuration of a second-generation motor molecule has been determined by a method other than CD spectroscopy
    • This is the first example described in the literature in which the absolute configuration of a second-generation motor molecule has been determined by a method other than CD spectroscopy.
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    • We acknowledge that this value may differ ±10, from the density of gold in the nanoparticle: O. D. Häberlen, S.-C. Chung, M. Stener, N. Rösch; J. Chem. Phys. 1997, 106, 5189
    • We acknowledge that this value may differ (±10%) from the density of gold in the nanoparticle: O. D. Häberlen, S.-C. Chung, M. Stener, N. Rösch; J. Chem. Phys. 1997, 106, 5189.
  • 100
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    • Allowing for a possible error in molar CD measurements of ±5 %.
    • Allowing for a possible error in molar CD measurements of ±5 %.
  • 102
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    • Calculated by using a structure of 44 minimized by MM2.
    • Calculated by using a structure of 44 minimized by MM2.
  • 103
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    • A reduction in the intensity of the long-wavelength absorption was observed upon formation of the unstable isomer of 2.[6
    • [6]
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    • Calculated by comparing the intensity of the CD absorption at 317 nm.
    • Calculated by comparing the intensity of the CD absorption at 317 nm.
  • 105
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    • A number of authors have reported CD spectra of metal nanoparticles protected with chiral nonracemic ligands, but none have described any effects of macroscopic anisotropy. Selected examples
    • A number of authors have reported CD spectra of metal nanoparticles protected with chiral nonracemic ligands, but none have described any effects of macroscopic anisotropy. Selected examples:
  • 110
    • 57649184096 scopus 로고    scopus 로고
    • The composition of the photostationary state mixture was determined by comparison of the relative integrals of the absorptions of the stable and unstable isomers, specifically by using protons of the methyl substituent at the stereogenic center (δ, 0.54 in the stable isomer vs. 0.90 ppm in the unstable isomer) and the aromatic protons at δ= 7.6-7.9 ppm to compare the ratio of stable to unstable, and the absorptions of the methoxyl groups to evaluate cis:trans ratios
    • The composition of the photostationary state mixture was determined by comparison of the relative integrals of the absorptions of the stable and unstable isomers, specifically by using protons of the methyl substituent at the stereogenic center (δ = 0.54 in the stable isomer vs. 0.90 ppm in the unstable isomer) and the aromatic protons at δ= 7.6-7.9 ppm to compare the ratio of stable to unstable, and the absorptions of the methoxyl groups to evaluate cis:trans ratios.


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