메뉴 건너뛰기




Volumn 122, Issue 39, 2000, Pages 9486-9494

Multiple-bridged bis-tetrathiafulvalenes: New synthetic protocols and spectroelectrochemical investigations

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; TETRATHIAFULVALENE DERIVATIVE;

EID: 0034605474     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000537c     Document Type: Article
Times cited : (130)

References (49)
  • 7
    • 37049133407 scopus 로고
    • 3CN) at room temperature when oxidizing a relatively concentrated solution of TTF (ca. 5 mM). This absorption disappeared at low concentration (ca. 0.5 mM) but increased on a thin film of TTF-derivatized polythiophenes, confirming its assignment to a dimer.
    • (1970) J. Chem. Soc., Chem. Commun. , pp. 1453
    • Wudl, F.1    Smith, G.M.2    Hufnagel, E.J.3
  • 8
    • 84936288766 scopus 로고
    • 3CN) at room temperature when oxidizing a relatively concentrated solution of TTF (ca. 5 mM). This absorption disappeared at low concentration (ca. 0.5 mM) but increased on a thin film of TTF-derivatized polythiophenes, confirming its assignment to a dimer
    • 3CN) at room temperature when oxidizing a relatively concentrated solution of TTF (ca. 5 mM). This absorption disappeared at low concentration (ca. 0.5 mM) but increased on a thin film of TTF-derivatized polythiophenes, confirming its assignment to a dimer.
    • (1973) Liebigs Ann. Chem. , pp. 310
    • Hünig, S.1    Kiesslich, G.2    Quast, H.3    Scheutzow, D.4
  • 11
    • 0001393574 scopus 로고
    • The ability of very short bridges to facilitate the formation of an intramolecular MV complex has also been observed in the crystal structure of the radical cation salt of a TTF twin donor containing one methylenedithio bridging unit: Izuoka, A.; Kumai, R.; Sugawara, T. Chem. Lett. 1992, 285. Oxidation of mono-bridged bis-TTF derivatives has also been studied by Cava and co-workers: Sudmale, I. V.; Tormos, G. V.; Khodorkovsky, V. Y.; Edzina, A. S.; Neilands, O. J.; Cava, M. P. J. Org. Chem. 1993, 58, 1355.
    • (1992) Chem. Lett. , pp. 285
    • Izuoka, A.1    Kumai, R.2    Sugawara, T.3
  • 12
    • 0001393574 scopus 로고
    • The ability of very short bridges to facilitate the formation of an intramolecular MV complex has also been observed in the crystal structure of the radical cation salt of a TTF twin donor containing one methylenedithio bridging unit: Izuoka, A.; Kumai, R.; Sugawara, T. Chem. Lett. 1992, 285. Oxidation of mono-bridged bis-TTF derivatives has also been studied by Cava and co-workers: Sudmale, I. V.; Tormos, G. V.; Khodorkovsky, V. Y.; Edzina, A. S.; Neilands, O. J.; Cava, M. P. J. Org. Chem. 1993, 58, 1355.
    • (1993) J. Org. Chem. , vol.58 , pp. 1355
    • Sudmale, I.V.1    Tormos, G.V.2    Khodorkovsky, V.Y.3    Edzina, A.S.4    Neilands, O.J.5    Cava, M.P.6
  • 18
    • 0342663322 scopus 로고    scopus 로고
    • note
    • 2 (1101.79); C, 43.61; H, 4.39; N, 2.54; S, 46.56. Found: C, 43.64; H, 4.36; N, 2.49; S, 46.71.
  • 19
    • 0342663323 scopus 로고    scopus 로고
    • note
    • 2/cyclohexane 1:3], yielding 4a (1.01 g, 72%) as an orange glass.
  • 21
    • 0343533564 scopus 로고    scopus 로고
    • note
    • 2 (1468.68): C, 49.48; H, 5.01; N, 3.81. Found: C, 49.51; H, 4.94; N, 3.83.
  • 23
    • 33748212323 scopus 로고
    • Alternative procedures for preparing TTF-belts: (a) Adam, M.; Enkelmann, V.; Räder, H.-J.; Röhrich, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 309. (b) Matsuo, K.; Takimiya, K.; Aso, Y.; Otsubo, T.; Ogura, F. Chem. Lett. 1995, 523.
    • (1995) Chem. Lett. , pp. 523
    • Matsuo, K.1    Takimiya, K.2    Aso, Y.3    Otsubo, T.4    Ogura, F.5
  • 24
    • 0343969370 scopus 로고    scopus 로고
    • note
    • +).
  • 29
    • 33845282499 scopus 로고
    • For studies on acid-catalyzed isomerization of TTF, see: Souizi, A.; Robert, A. J. Org. Chem. 1987, 52, 1610.
    • (1987) J. Org. Chem. , vol.52 , pp. 1610
    • Souizi, A.1    Robert, A.2
  • 30
    • 0343969368 scopus 로고    scopus 로고
    • note
    • 5Cl at 276 K. A yellow single crystal of 4b was selected by optical examination. X-ray data were collected at 294 K on an Enraf Nonius Mach 3 four circles diffractometer equipped with a graphite monochromator utilizing Mo Kα radiation (λ = 0.71073 Å). The structure was solved by direct methods (SIR) using MoIEN package programs [Crystal Structure Analysis: Molecular Enraf-Nonius (MoIEN), 1990. Delft Instruments X-ray Diffraction. B. V. Rontnenweg 1, 2624 BD Delft, The Netherlands] and was refined on F by the full-matrix least-squares method using anisotropic thermal parameters for S and isotropic ones for C. No absorption corrections were made. The H atoms were included in the calculation without refinement.
  • 32
    • 0343533562 scopus 로고    scopus 로고
    • -1 was used
    • -1 was used.
  • 33
    • 0342663320 scopus 로고
    • 6 (0.4 M) was used as the supporting electrolyte in all of the experiments. For more details, see: Gaillard, F.; Levillain, E. J. Electroanal. Chem. 1995, 398, 11.
    • (1995) J. Electroanal. Chem. , vol.398 , pp. 11
    • Gaillard, F.1    Levillain, E.2
  • 34
    • 0000980709 scopus 로고
    • 3CN. This enhanced ability of TMT-TTF relative to TTF to form dimers is probably a result of the four extra sulfur atoms which can facilitate dimer formation by favorable S-S interactions.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 945
    • Moses, P.R.1    Chambers, J.Q.2
  • 35
    • 0001241330 scopus 로고
    • 3CN. This enhanced ability of TMT-TTF relative to TTF to form dimers is probably a result of the four extra sulfur atoms which can facilitate dimer formation by favorable S-S interactions.
    • (1985) Zh. Org. Khim. , vol.21 , pp. 2009
    • Kreicberga, J.1    Neilands, O.2
  • 36
    • 0033615314 scopus 로고    scopus 로고
    • ESR experiments were run on a Bruker ESP 300 spectrometer driven by the Bruker ESP 1600 computer program. Using this same equipment, similar experiments probing dimer formation of tetrathienylenevinylenes were carried out earlier: Levillain, E.; Roncali, J. J. Am. Chem. Soc. 1999, 121, 8760.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8760
    • Levillain, E.1    Roncali, J.2
  • 37
    • 0343097619 scopus 로고    scopus 로고
    • 23 measured an ESR signal in their studies of the TMT-TTF radical cation. However, in light of their deviating spectral data, we question if their solution did, in fact, contain the pure and fully mono-oxidized TMT-TTF
    • 23 measured an ESR signal in their studies of the TMT-TTF radical cation. However, in light of their deviating spectral data, we question if their solution did, in fact, contain the pure and fully mono-oxidized TMT-TTF.
  • 38
    • 0343533561 scopus 로고    scopus 로고
    • max = 706 nm), which is in good agreement with the spectroelectrochemical result, whereas neither of our experiments substantiate the two high-energy absorptions
    • max = 706 nm), which is in good agreement with the spectroelectrochemical result, whereas neither of our experiments substantiate the two high-energy absorptions.
  • 43
    • 0342663319 scopus 로고    scopus 로고
    • 6 as the supporting electrolyte. Counter and working electrodes were made of Pt, and the reference electrode was Ag/AgCl
    • 6 as the supporting electrolyte. Counter and working electrodes were made of Pt, and the reference electrode was Ag/AgCl.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.