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Volumn 74, Issue 6, 2009, Pages 2374-2379

Using photoresponsive end-closing and end-opening reactions for the synthesis and disassembly of [2]rotaxanes: Implications for dynamic covalent chemistry

Author keywords

[No Author keywords available]

Indexed keywords

COVALENT CHEMISTRIES; DIALKYLAMMONIUM; DYNAMIC COVALENT CHEMISTRIES; ELEVATED TEMPERATURES; GOOD YIELDS; GUIDED SELF ASSEMBLIES; OPENING PROCESS; OPENING REACTIONS; PHOTORESPONSIVE; POLAR SOLVENTS; ROOM TEMPERATURES; ROTAXANES; TWO COMPONENTS; UV IRRADIATIONS;

EID: 64149127018     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025143     Document Type: Article
Times cited : (21)

References (84)
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    • Selected reviews on photoresponsive artificial molecular switches: (a) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846-853.
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    • Selected reviews on photocontrolled translational motion: (a) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445-455.
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    • For the use of transition metal complexes as photosensitizers, with switching involving association and dissociation of a pseudorotaxane, see: a
    • For the use of transition metal complexes as photosensitizers, with switching involving association and dissociation of a pseudorotaxane, see: (a) Ashton, P. R.; Balzani, V.; Kocian, O.; Prodi, L.; Spencer. N.; Stoddart, J. F. J. Am. Chem. Soc. 1998, 120, 11190-11191.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 11190-11191
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    • Dynamic syntheses of rotaxanes through imine formation: (a) Cantrill, S. J.; Rowan, S. J.; Stoddart, J. F. Org. Lett. 1999, 1, 1363-1366.
    • Dynamic syntheses of rotaxanes through imine formation: (a) Cantrill, S. J.; Rowan, S. J.; Stoddart, J. F. Org. Lett. 1999, 1, 1363-1366.
  • 59
    • 0034340806 scopus 로고    scopus 로고
    • Dynamic syntheses of rotaxanes through sulfur-sulfur bond formation: (a) Furusho, Y.; Hasegawa, T.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18-19.
    • Dynamic syntheses of rotaxanes through sulfur-sulfur bond formation: (a) Furusho, Y.; Hasegawa, T.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18-19.
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    • Dynamic synthesis of a rotaxane through trityl thioether linkage: Furusho, Y.; Oku, T.; Rajkumar, G. A.; Takata, T. Chem. Lett. 2004, 33, 52-53.
    • Dynamic synthesis of a rotaxane through trityl thioether linkage: Furusho, Y.; Oku, T.; Rajkumar, G. A.; Takata, T. Chem. Lett. 2004, 33, 52-53.
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    • Dynamic syntheses of rotaxanes using olefin metathesis: (a) Coumans, R. G. E.; Elemans, J. A. A. W.; Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Angew. Chem., Int. Ed. 2003, 42, 650-654.
    • Dynamic syntheses of rotaxanes using olefin metathesis: (a) Coumans, R. G. E.; Elemans, J. A. A. W.; Thordarson, P.; Nolte, R. J. M.; Rowan, A. E. Angew. Chem., Int. Ed. 2003, 42, 650-654.
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    • Part of this work was published as apreliminary communication: Tokunaga, Y.; Akasaka, K.; Hisada, K.; Shimomura, Y.; Kakuchi, S. Chem. Commun. 2003, 2250-2251.
    • Part of this work was published as apreliminary communication: Tokunaga, Y.; Akasaka, K.; Hisada, K.; Shimomura, Y.; Kakuchi, S. Chem. Commun. 2003, 2250-2251.
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    • The use of 9-fluorenone, duroquinone, and pyrene as photosensitizers provided the [2]rotaxane (Z)-4 in 54% (NMR yield: 79%), 71% (79%), and 58% (77%) yields, respectively.
    • The use of 9-fluorenone, duroquinone, and pyrene as photosensitizers provided the [2]rotaxane (Z)-4 in 54% (NMR yield: 79%), 71% (79%), and 58% (77%) yields, respectively.
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    • 12f
    • 12f
  • 73
    • 64149129042 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 75
    • 0032803177 scopus 로고    scopus 로고
    • Rotaxane-encapsulation can enhance the stability of the axle's components; for examples, see: a
    • Rotaxane-encapsulation can enhance the stability of the axle's components; for examples, see: (a) Parham, A. H.; Windisch, B.; Vögtle, F. Eur. J. Org. Chem. 1999, 1233-1238.
    • (1999) Eur. J. Org. Chem , pp. 1233-1238
    • Parham, A.H.1    Windisch, B.2    Vögtle, F.3
  • 82
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    • A Z to E isomerization reaction proceeded in the absence of the radical scavenger.
    • A Z to E isomerization reaction proceeded in the absence of the radical scavenger.
  • 83
    • 64149124171 scopus 로고    scopus 로고
    • deg is the rate constant of the thermal degradation reaction, and ΔG‡ is the activation free energy, given by the activation enthalpy (ΔH‡) and activation entropy (ΔS‡) as ΔG‡ = ΔH‡ - TΔS‡.
    • deg is the rate constant of the thermal degradation reaction, and ΔG‡ is the activation free energy, given by the activation enthalpy (ΔH‡) and activation entropy (ΔS‡) as ΔG‡ = ΔH‡ - TΔS‡.


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