메뉴 건너뛰기




Volumn 131, Issue 32, 2009, Pages 11571-11580

A push-button molecular switch

Author keywords

[No Author keywords available]

Indexed keywords

[2]CATENANE; CATENANES; EXPERIMENTAL TECHNIQUES; FACILE SYNTHESIS; HIGH RATE; HIGH YIELD; INTERLOCKED MOLECULES; MECHANICAL SWITCHING; MOLECULAR SWITCHES; QUANTUM MECHANICAL; SWITCHABLE; SWITCHING MECHANISM; TETRATHIAFULVALENES;

EID: 68849102764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904104c     Document Type: Article
Times cited : (100)

References (89)
  • 13
    • 0003570337 scopus 로고    scopus 로고
    • Diederich, F, Stang, P. J, Eds, Wiley-VCH: Weinheim, Germany
    • (g) Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
    • (1999) Templated Organic Synthesis
  • 19
    • 0003542983 scopus 로고    scopus 로고
    • Sauvauge, J.-P, Dietrich-Buchecker, C, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Molecular Catenanes, Rotaxanes, and Knots; Sauvauge, J.-P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
    • (1999) Molecular Catenanes, Rotaxanes, and Knots
  • 31
    • 33846503504 scopus 로고    scopus 로고
    • (f) Ball, P. Nature 2007, 445, 362-363.
    • (2007) Nature , vol.445 , pp. 362-363
    • Ball, P.1
  • 38
    • 0004240038 scopus 로고    scopus 로고
    • Feringa, B. L, Ed, Wiley-VCH: Weinheim, Germany
    • (f) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
    • (2001) Molecular Switches
  • 55
    • 0034604562 scopus 로고    scopus 로고
    • For a comprehensive review of Glaser, Eglinton, and related alkyne couplings, see: a
    • For a comprehensive review of Glaser, Eglinton, and related alkyne couplings, see: (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 2632-2657
    • Siemsen, P.1    Livingston, R.C.2    Diederich, F.3
  • 67
    • 0347088929 scopus 로고    scopus 로고
    • Compound 3 was synthesized using a procedure slightly modified from that given in the following reference: Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Perkins, J.; Jeppesen, J. O.; Fabio, A. D.; Ballardini, R.; Gandolfi, M. T.; Venturi, M.; Balzani, V.; Stoddart, J. F. Chem. - Eur. J. 2004, 10, 155-172.
    • Compound 3 was synthesized using a procedure slightly modified from that given in the following reference: Tseng, H.-R.; Vignon, S. A.; Celestre, P. C.; Perkins, J.; Jeppesen, J. O.; Fabio, A. D.; Ballardini, R.; Gandolfi, M. T.; Venturi, M.; Balzani, V.; Stoddart, J. F. Chem. - Eur. J. 2004, 10, 155-172.
  • 68
    • 68849095984 scopus 로고    scopus 로고
    • 6, facilitating its purification as the sole charged component in an assortment of organic products derived from Eglinton coupling of 4.
    • 6, facilitating its purification as the sole charged component in an assortment of organic products derived from Eglinton coupling of 4.
  • 69
    • 68849098156 scopus 로고    scopus 로고
    • Crystal description: C79.50H93F24N 12.50O8P4S4; Mr, 2059.78; triclinic; space group P1; a, 14.0138(4) Å, b, 14.0734(2) Å, c, 25.1493(5) Å, α, 98.2070(10)°, β, 105.1000(10)°, γ, 91.9490(10)°; V, 4726.5(2) Å3; Z, 2; T, 100(2) K; 65124 reflections collected, 16991 independent reflections (R int, 0.0375, RF, 0.0979, wR2, 0.2687. Disordered MeCN molecules as well as PF6- counterions are also present within the structure
    • - counterions are also present within the structure.
  • 70
    • 68849121461 scopus 로고    scopus 로고
    • A mean π-π distance of 3.35 Å between the bipyridinium faces and the encircled TTF unit was observed.
    • A mean π-π distance of 3.35 Å between the bipyridinium faces and the encircled TTF unit was observed.
  • 71
    • 68849101601 scopus 로고    scopus 로고
    • [C-H⋯O] short contacts of 2.41, 2.54, and 2.34 Å with corresponding angles of 166.7, 117.24, and 169.06° were measured for the second, third, and second oxygens away from the TTF unit, respectively.
    • [C-H⋯O] short contacts of 2.41, 2.54, and 2.34 Å with corresponding angles of 166.7, 117.24, and 169.06° were measured for the second, third, and second oxygens away from the TTF unit, respectively.
  • 72
    • 30344457892 scopus 로고    scopus 로고
    • 4+-based [2]catenanes, see: Vignon, S. A.; Stoddart, J. F. Collect. Czech. Chem. Commun. 2005, 70, 1493-1576.
    • 4+-based [2]catenanes, see: Vignon, S. A.; Stoddart, J. F. Collect. Czech. Chem. Commun. 2005, 70, 1493-1576.
  • 74
    • 0037418978 scopus 로고    scopus 로고
    • For a detailed description of this chemical oxidant and the reasons we used it here, see: a
    • For a detailed description of this chemical oxidant and the reasons we used it here, see: (a) Tseng, H.-R.; Vignon, S. A.; Stoddart, J. F. Angew. Chem., Int. Ed. 2003, 42, 1491-1495.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 1491-1495
    • Tseng, H.-R.1    Vignon, S.A.2    Stoddart, J.F.3
  • 75
    • 6844239208 scopus 로고    scopus 로고
    • For a review of this and other chemical oxidants commonly used in NMR studies, see: b
    • For a review of this and other chemical oxidants commonly used in NMR studies, see: (b) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
    • (1996) Chem. Rev , vol.96 , pp. 877-910
    • Connelly, N.G.1    Geiger, W.E.2
  • 76
    • 68849091010 scopus 로고    scopus 로고
    • The first-order decay from the MSCC, where the CBPQT4+ ring encircles the butadiyne unit, to the GSCC, where the CBPQT4+ ring encircles the TTF unit, can be fitted using the general formula given in eq 1: Nbutadiyne(t, N°butadiyne, Ntotal, N°butadiyne) exp(-t/τ, 1) where N°butadiyne is the equilibrium population 0, of the MSCC in the ground state at the beginning of the experiment, Nbutadiyne is the metastable-state population at the time t elapsed from the second reductive peak of the first scan to where the first oxidative peak for unencircled TTF would occur in the second successive scan, Ntotal is the total population of translational isomers, and τ is the lifetime of the metastable state. Solving eq 1 for 1/τ yields the rate constant k for the relaxation process, which may be
    • ‡ of 14.8 ± 1 kcal/mol for the MSCC-to-GSCC relaxation process.
  • 77
    • 68849101602 scopus 로고    scopus 로고
    • As opposed to CV, spectroelectrochemistry relies on the complete oxidation or reduction of the analyte across the entire path length of the cell. The long waiting times are therefore not a reflection of the kinetics of switching a single molecule but of the diffusion of molecules to and from the working electrode
    • As opposed to CV, spectroelectrochemistry relies on the complete oxidation or reduction of the analyte across the entire path length of the cell. The long waiting times are therefore not a reflection of the kinetics of switching a single molecule but of the diffusion of molecules to and from the working electrode.
  • 78
    • 0006894480 scopus 로고    scopus 로고
    • The cell is an optically transparent thin-layer electrochemical (OTTLE) cell with an optical path of 1 mm that uses a Pt grid as the working electrode, a Pt wire as the counter electrode, and a Ag/AgCl reference electrode. For the construction of this cell, see: Babaei, A.; Connor, P. A.; McQuillan, A. J.; Umapathy, S. J. Chem. Educ. 1997, 74, 1200-1204.
    • The cell is an optically transparent thin-layer electrochemical (OTTLE) cell with an optical path of 1 mm that uses a Pt grid as the working electrode, a Pt wire as the counter electrode, and a Ag/AgCl reference electrode. For the construction of this cell, see: Babaei, A.; Connor, P. A.; McQuillan, A. J.; Umapathy, S. J. Chem. Educ. 1997, 74, 1200-1204.
  • 79
    • 68849120644 scopus 로고    scopus 로고
    • The attenuation in signal intensity (Figure 6) is attributed to electrochemical destruction of the molecule over the course of the investigation.
    • The attenuation in signal intensity (Figure 6) is attributed to electrochemical destruction of the molecule over the course of the investigation.
  • 83
    • 68849089732 scopus 로고    scopus 로고
    • Our calculations did not include entropic corrections, which could lower the energy for the MSCC and the circumrotation barrier by 2-4 kcal mol -1 as a consequence of the greater vibrational freedom of the butadiyne and the oligomeric ethylene glycol chain inside the CBPQT4+ ring
    • 4+ ring.
  • 84
    • 68849094360 scopus 로고    scopus 로고
    • This somewhat crude estimate of the proposed electronic transition between the butadiyne and CBPQT4+ ring in 16+ is based upon energy levels calculated without applying a solvent correction for 14, and while there would be some variation in the energies as a consequence of the added charge, we speculate that the error in the calculation would amount to no more than 40 nm
    • 4+, and while there would be some variation in the energies as a consequence of the added charge, we speculate that the error in the calculation would amount to no more than 40 nm.
  • 85
    • 68849115997 scopus 로고    scopus 로고
    • Originally reported in ref 6g
    • Originally reported in ref 6g.
  • 89
    • 68849098768 scopus 로고    scopus 로고
    • Jaguar, version 7.0; Schrödinger, LLC: New York, 2007
    • Jaguar, version 7.0; Schrödinger, LLC: New York, 2007.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.