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Volumn 130, Issue 8, 2008, Pages 2593-2601

Three state redox-active molecular shuttle that switches in solution and on a surface

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; HYDROGEN BONDS; MACROMOLECULES; NAPHTHALENE; REDOX REACTIONS; SELF ASSEMBLED MONOLAYERS;

EID: 39749171704     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077223a     Document Type: Article
Times cited : (150)

References (124)
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    • For the first example of an amide-based molecular shuttle see: b
    • For the first example of an amide-based molecular shuttle see: (b) Lane, A. S.; Leigh, D. A.; Murphy, A. J. Am. Chem. Soc. 1997, 119, 11092-11093.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 11092-11093
    • Lane, A.S.1    Leigh, D.A.2    Murphy, A.3
  • 9
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    • Co-conformation refers to the relative positions of the mechanically interlocked components with respect to each other, see: Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2070.
    • "Co-conformation" refers to the relative positions of the mechanically interlocked components with respect to each other, see: Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2070.
  • 40
  • 57
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    • For other examples of photochemically responsive amide-based molecular shuttles, see ref 9 and: (a) Wurpel, G. W. H, Brouwer, A. M, van Stokkum, I. H. M, Farran, A, Leigh, D. A. J. Am. Chem. Soc. 2001, 123, 11327-11328
    • For other examples of photochemically responsive amide-based molecular shuttles, see ref 9 and: (a) Wurpel, G. W. H.; Brouwer, A. M.; van Stokkum, I. H. M.; Farran, A.; Leigh, D. A. J. Am. Chem. Soc. 2001, 123, 11327-11328.
  • 64
    • 0037717476 scopus 로고    scopus 로고
    • For examples of chemically responsive amide-based molecular shuttles, see refs 3b, 8b and the following: (a) Da Ros, T, Guldi, D. M, Morales, A. F, Leigh, D. A, Prato, M, Turco, R. Org. Lett. 2003, 5, 689-691
    • For examples of chemically responsive amide-based molecular shuttles, see refs 3b, 8b and the following: (a) Da Ros, T.; Guldi, D. M.; Morales, A. F.; Leigh, D. A.; Prato, M.; Turco, R. Org. Lett. 2003, 5, 689-691.
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    • For examples of pH-responsive amide-based molecular shuttles, see: (a) Keaveney, C. M, Leigh, D. A. Angew. Chem, Int. Ed. 2004, 43, 1222-1224
    • For examples of pH-responsive amide-based molecular shuttles, see: (a) Keaveney, C. M.; Leigh, D. A. Angew. Chem., Int. Ed. 2004, 43, 1222-1224.
  • 72
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    • For examples of transition metal-binding amide-based molecular shuttles, see: (a) Marlin, D. S, Cabrera, D. G, Leigh, D. A, Slawin, A. M. Z. Angew. Chem, Int. Ed. 2006, 45, 77-83
    • For examples of transition metal-binding amide-based molecular shuttles, see: (a) Marlin, D. S.; Cabrera, D. G.; Leigh, D. A.; Slawin, A. M. Z. Angew. Chem., Int. Ed. 2006, 45, 77-83.
  • 82
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    • In some supramolecular complexes where the oxidation state of an imide derivative has been used to control the binding constant, although hydrogen bonding to the imide carbonyls is involved, the overall association constant actually decreased on increasing imide charge as a consequence of stacking interactions with π-electron-rich aromatics. See: a
    • In some supramolecular complexes where the oxidation state of an imide derivative has been used to control the binding constant, although hydrogen bonding to the imide carbonyls is involved, the overall association constant actually decreased on increasing imide charge as a consequence of stacking interactions with π-electron-rich aromatics. See: (a) Goodman, A.; Breinlinger, E.; Ober, M.; Rotello, V. M. J. Am. Chem. Soc. 2001, 123, 6213-6214.
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  • 87
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    • Imides have also been used as fluorescent reporter units in rotaxane-based shuttles while playing no apparent role in interactions with the macrocycle. See, for example: Qu, D.-H, Ji, F.-Y, Wang, Q.-C, Tian, H. Adv. Mater. 2006, 18, 2035-2038, and references therein
    • Imides have also been used as fluorescent reporter units in rotaxane-based shuttles while playing no apparent role in interactions with the macrocycle. See, for example: Qu, D.-H.; Ji, F.-Y.; Wang, Q.-C.; Tian, H. Adv. Mater. 2006, 18, 2035-2038, and references therein.
  • 88
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    • The nomenclature used to denote individual rotaxane states and isomers follows conventions adopted in previous papers (e.g, ref 14b, Namely, a bolded compound number refers to a given structural formula; the oxidation state is denoted by a superscript suffix the absence of which indicates the neutral form, a prefix succ or ndi denotes the position of the macrocycle in a particular translational isomer
    • The nomenclature used to denote individual rotaxane states and isomers follows conventions adopted in previous papers (e.g., ref 14b). Namely, a bolded compound number refers to a given structural formula; the oxidation state is denoted by a superscript suffix (the absence of which indicates the neutral form); a prefix succ or ndi denotes the position of the macrocycle in a particular translational isomer.
  • 89
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    • When a group that is too bulky for the macrocycle to pass over was placed in between the two stations in 1, the CV of the rotaxane mirrored that of the corresponding thread; i.e, the shift in the redox potential in the rotaxane must arise from shuttling of the macrocycle to the reduced station. See ref 14b
    • When a group that is too bulky for the macrocycle to pass over was placed in between the two stations in 1, the CV of the rotaxane mirrored that of the corresponding thread; i.e., the shift in the redox potential in the rotaxane must arise from shuttling of the macrocycle to the reduced station. See ref 14b.
  • 91
  • 95
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    • Investigation of molecular-level motions in drop-casted, vacuum-evaporated or spin-coated thin films or polycrystalline samples of catenanes and rotaxanes is another emerging area of interest. See, for example: (a) Cavallini, M.; Biscarini, F.; León, S.; Zerbetto, F.; Bottari, G.; Leigh, D. A. Science 2003, 299, 531-531.
    • Investigation of molecular-level motions in drop-casted, vacuum-evaporated or spin-coated thin films or polycrystalline samples of catenanes and rotaxanes is another emerging area of interest. See, for example: (a) Cavallini, M.; Biscarini, F.; León, S.; Zerbetto, F.; Bottari, G.; Leigh, D. A. Science 2003, 299, 531-531.
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    • Polyrotaxane architectures also allow preparation of solid-state interlocked species. For examples of electroactive polyrotaxanes, see: a
    • Polyrotaxane architectures also allow preparation of solid-state interlocked species. For examples of electroactive polyrotaxanes, see: (a) Zhu, S. S.; Carroll, P. J.; Swager, T. M. J. Am. Chem. Soc. 1996, 118, 8713-8714.
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    • In alkaline aqueous systems, this has been shown to be the result of partial reversible reductive desorption of the thiolates. The exact potential at which this occurs varies with certain structural features, and consequently this process has been widely studied as a method for probing the molecular structure of monolayers. See, for example: (a) Widrig, C. A, Chung, C, Porter, M. D. J. Electroanal. Chem. 1991, 310, 335-359
    • In alkaline aqueous systems, this has been shown to be the result of partial reversible reductive desorption of the thiolates. The exact potential at which this occurs varies with certain structural features, and consequently this process has been widely studied as a method for probing the molecular structure of monolayers. See, for example: (a) Widrig, C. A.; Chung, C.; Porter, M. D. J. Electroanal. Chem. 1991, 310, 335-359.
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    • Even under neutral conditions, or in organic solvents where reductive desorption is not observed within the solvent window, alkanethiolate SAMs are still destroyed at negative potentials. The details of this complex, kinetically controlled, process are less well understood. See, for example: (d) Everett, W. R.; Welch, T. L.; Reed, L.; Fritsch-Faules, I. Anal. Chem. 1995, 67, 292-298.
    • Even under neutral conditions, or in organic solvents where reductive desorption is not observed within the solvent window, alkanethiolate SAMs are still destroyed at negative potentials. The details of this complex, kinetically controlled, process are less well understood. See, for example: (d) Everett, W. R.; Welch, T. L.; Reed, L.; Fritsch-Faules, I. Anal. Chem. 1995, 67, 292-298.
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    • See also: (g) Finklea, H. O. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1996; Vol. 19, p 109.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.