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Volumn 129, Issue 23, 2007, Pages 7354-7363

Two classes of alongside charge-transfer interactions defined in one [2]catenane

Author keywords

[No Author keywords available]

Indexed keywords

BIPYRIDINIUM MOIETIES; CATENANE; HYDROQUINONE (HQ); TETRATHIAFULVALENE (TTF);

EID: 34250839559     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja069047w     Document Type: Article
Times cited : (55)

References (131)
  • 24
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    • (c) Lehn, J. M. Science 2002, 295, 2400-2403.
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    • Sauvage, J.-P, Dietrich-Buchecker, C, Eds, VCH-Wiley: Weinheim
    • (b) Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P., Dietrich-Buchecker, C., Eds.; VCH-Wiley: Weinheim, 1999.
    • (1999) Molecular Catenanes, Rotaxanes and Knots
  • 58
    • 0001227655 scopus 로고    scopus 로고
    • For an introduction and overview over the wide array of weak noncovalent interactions please refer to the dollowing rets: (a) Hunter, C. A, Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534
    • For an introduction and overview over the wide array of weak noncovalent interactions please refer to the dollowing rets: (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
  • 62
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    • 4+, see: Li, Z.-T.; Becher, J. Chem. Commun. 1996, 639-640 and ref 6e.
    • 4+, see: Li, Z.-T.; Becher, J. Chem. Commun. 1996, 639-640 and ref 6e.
  • 63
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    • 4+, see refs 6c,f.
    • 4+, see refs 6c,f.
  • 64
    • 0031269049 scopus 로고    scopus 로고
    • For edge-to-face CT interactions involving heterocyclic nitrogen and diazapyrenium cations, see
    • (c) For edge-to-face CT interactions involving heterocyclic nitrogen and diazapyrenium cations, see: Becker, H.-C.; Broo, A.; Nordén, B. J. Phys. Chem. 1997, 101, 8853-8860.
    • (1997) J. Phys. Chem , vol.101 , pp. 8853-8860
    • Becker, H.-C.1    Broo, A.2    Nordén, B.3
  • 65
    • 0032207611 scopus 로고    scopus 로고
    • For inter-TTF edge-to-face arrangements of a neutral TTF dimer and the CT interactions of a radical cation, see: Batsanov, A. S, John, D. E, Bryce, M. R, Howard, J. A. K. Adv. Mater. 1998, 10, 1360-1363
    • (d) For inter-TTF edge-to-face arrangements of a neutral TTF dimer and the CT interactions of a radical cation, see: Batsanov, A. S.; John, D. E.; Bryce, M. R.; Howard, J. A. K. Adv. Mater. 1998, 10, 1360-1363.
  • 66
    • 84961980623 scopus 로고    scopus 로고
    • For [CH⋯π] edge-to-face CT interactions involving pyridinium cations, see: Acharya, P.; Plashkevych, O.; Morita, C.; Yamada, S.; Chattopadhyaya, J. J. Org. Chem. 2003, 68, 1529-1538.
    • (e) For [CH⋯π] edge-to-face CT interactions involving pyridinium cations, see: Acharya, P.; Plashkevych, O.; Morita, C.; Yamada, S.; Chattopadhyaya, J. J. Org. Chem. 2003, 68, 1529-1538.
  • 75
    • 0347088929 scopus 로고    scopus 로고
    • Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Perkins, J.; Jeppesen, J. O.; Di, Fabio, A.; Ballardini, R.; Gandolfi, M. T.; Venturi, M.; Balzani, V.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 155-172.
    • (c) Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Perkins, J.; Jeppesen, J. O.; Di, Fabio, A.; Ballardini, R.; Gandolfi, M. T.; Venturi, M.; Balzani, V.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 155-172.
  • 94
    • 0042074624 scopus 로고    scopus 로고
    • For an edge-to-face TTF-to-xylene [S⋯π] interaction of a model host-guest complex, see: Ercolani, G.; Mencarelli, P. J. Org. Chem. 2003, 68, 6470-6473.
    • For an edge-to-face TTF-to-xylene [S⋯π] interaction of a model host-guest complex, see: Ercolani, G.; Mencarelli, P. J. Org. Chem. 2003, 68, 6470-6473.
  • 99
    • 34250869411 scopus 로고    scopus 로고
    • 6.
    • 6.
  • 100
    • 34250825171 scopus 로고    scopus 로고
    • For another example of isomeric selectivity in the formation of [2]catenanes, refer to ref 6d
    • For another example of isomeric selectivity in the formation of [2]catenanes, refer to ref 6d.
  • 101
    • 34250807725 scopus 로고    scopus 로고
    • This assignment is further substantiated and confirmed by the relationship between the observed UV-vis-NIR absorption spectroscopic data and the cis/trans isomer ratio of the [2]catenane as confirmed by molecular modeling
    • This assignment is further substantiated and confirmed by the relationship between the observed UV-vis-NIR absorption spectroscopic data and the cis/trans isomer ratio of the [2]catenane as confirmed by molecular modeling.
  • 102
    • 34250896648 scopus 로고    scopus 로고
    • 4+ cyclophane.
    • 4+ cyclophane.
  • 103
    • 34250813559 scopus 로고    scopus 로고
    • Crystallographic data for 1·4PF6·(CD 3CN)7 at 133(2) K with Mo Kα radiation (λ, 0.71069 Å, 1·4PF6: triclinic, space group P-1, a, 13.571-(8) Å, b, 14.252(8) Å, c, 27.108(15) Å, α, 97.841(12)°, β, 91.323-(12)°, χ, 106.338(12)°, Z, 2, R1, 0.0887. wR2 all data, 0.2497, GOF, 0.810
    • 6: triclinic, space group P-1, a = 13.571-(8) Å, b = 14.252(8) Å, c = 27.108(15) Å, α = 97.841(12)°, β = 91.323-(12)°, χ = 106.338(12)°, Z = 2, R1 = 0.0887. wR2 (all data) = 0.2497, GOF = 0.810.
  • 114
    • 34250844249 scopus 로고    scopus 로고
    • No difference in the electrochemical data collected was observed when comparing the electrochemical data of the predominately cis isomer (9:1) bismacrocycle 6 to the 1:1 isomeric cis/trans mixture of the bismacrocycle 6
    • No difference in the electrochemical data collected was observed when comparing the electrochemical data of the predominately cis isomer (9:1) bismacrocycle 6 to the 1:1 isomeric cis/trans mixture of the bismacrocycle 6.
  • 115
    • 34250841622 scopus 로고    scopus 로고
    • No observable difference in the electrochemical data was observed when the experiments were carried out on either a 1:1 mixture of the cis and the trans isomer or the purified TTF isomers
    • No observable difference in the electrochemical data was observed when the experiments were carried out on either a 1:1 mixture of the cis and the trans isomer or the purified TTF isomers.
  • 116
    • 34250798960 scopus 로고    scopus 로고
    • No difference in the electrochemical data collected was observed when the [2]catenane (95:5 cis/trans) prepared from the predominately cis isomer (9:1) bismacrocycle 6 or the [2]catenane (67:33 cis/trans) prepared from a 1:1 isomeric mixture of the bismacrocycle 6 was used in individual experiments.
    • No difference in the electrochemical data collected was observed when the [2]catenane (95:5 cis/trans) prepared from the predominately cis isomer (9:1) bismacrocycle 6 or the [2]catenane (67:33 cis/trans) prepared from a 1:1 isomeric mixture of the bismacrocycle 6 was used in individual experiments.
  • 117
    • 34250873773 scopus 로고    scopus 로고
    • For a detailed analysis of the electrochemical profile of the alongside interaction in a two-station [2]pseudorotaxane, please refer to refs 18c and 24
    • For a detailed analysis of the electrochemical profile of the alongside interaction in a two-station [2]pseudorotaxane, please refer to refs 18c and 24.
  • 119
  • 124
    • 34250817941 scopus 로고    scopus 로고
    • 4+ has been reported in the literature. Please refer to refs 18c and 24. In both cases, the alongside interaction was observed as a weak shoulder in the UV-vis-NIR absorption spectra and arose surreptitously.
    • 4+ has been reported in the literature. Please refer to refs 18c and 24. In both cases, the alongside interaction was observed as a weak shoulder in the UV-vis-NIR absorption spectra and arose surreptitously.


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