메뉴 건너뛰기




Volumn 124, Issue 47, 2002, Pages 14227-14238

A (π-extended tetrathiafulvalene)-fluorene conjugate. Unusual electrochemistry and charge transfer properties: The first observation of a covalent D2+-σ-A.- Redox state

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ESTERS; REDOX REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

EID: 0037184485     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja012518o     Document Type: Article
Times cited : (62)

References (93)
  • 13
    • 0000971557 scopus 로고
    • To date there is only one report on the coupling of substituted TTF and TCNQ: Panetta, C. A.; Baghdadchi, J.; Metzger, R. M. Mol. Mol. Cryst. Liq. Cryst. 1984, 107, 103-113. However, a difficult synthetic route and problems with purification precluded detailed characterization of the compound.
    • (1984) Mol. Mol. Cryst. Liq. Cryst. , vol.107 , pp. 103-113
    • Panetta, C.A.1    Baghdadchi, J.2    Metzger, R.M.3
  • 14
    • 28344451958 scopus 로고
    • Aviram, A.; Ratner, M. Chem. Phys. Lett. 1974, 29, 277-283. For recent discussions of this proposal see: Metzger, R. M. J. Mater. Chem. 1999, 9, 2027-2036.
    • (1974) Chem. Phys. Lett. , vol.29 , pp. 277-283
    • Aviram, A.1    Ratner, M.2
  • 15
    • 0032835693 scopus 로고    scopus 로고
    • Aviram, A.; Ratner, M. Chem. Phys. Lett. 1974, 29, 277-283. For recent discussions of this proposal see: Metzger, R. M. J. Mater. Chem. 1999, 9, 2027-2036.
    • (1999) J. Mater. Chem. , vol.9 , pp. 2027-2036
    • Metzger, R.M.1
  • 41
    • 2242473317 scopus 로고    scopus 로고
    • note
    • For synthetic details see the Supporting Information. A similar oxidation reaction giving the TTF radical cation salt was also observed under these conditions for 4-hydroxymethyl-TTF (ref 37).
  • 42
    • 2242477871 scopus 로고    scopus 로고
    • note
    • Only two reversible reductions have been observed for 19.
  • 44
    • 2242464318 scopus 로고    scopus 로고
    • note
    • CVs for the scan rates from 0.1 to 1.0 V only are shown on Figure 3 for clarity.
  • 46
    • 0000157456 scopus 로고
    • Young, A., Britton, G., Eds.; Chapman and Hall: London; Chapter 8
    • (a) Frank, H. A.; Cogdell, R. J. In Carotenoids in Photosynthesis; Young, A., Britton, G., Eds.; Chapman and Hall: London, 1993; Chapter 8, p 252.
    • (1993) Carotenoids in Photosynthesis , pp. 252
    • Frank, H.A.1    Cogdell, R.J.2
  • 48
    • 0034814924 scopus 로고    scopus 로고
    • An inversion of the standard potentials for the first and second electron transfer substantially depends on the structure of carotenoids: an inversion occurs in the oxidation of β-carotene and in the reduction of canthaxanthin, but not in the reduction of β-carotene or in the oxidation of canthaxanthin: Hapiot, P.; Kispert, L. D.; Konovalov, V. V.; Savéant. J.-M. J. Am. Chem. Soc. 2001, 123, 6669-6677.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 6669-6677
    • Hapiot, P.1    Kispert, L.D.2    Konovalov, V.V.3    Savéant, J.-M.4
  • 50
    • 2242437501 scopus 로고    scopus 로고
    • note
    • 0 species) and at low electrolyte concentration (to prevent its precipitation at low temperatures).
  • 54
    • 0000973171 scopus 로고
    • Chapman and Hall: London and New York
    • -1 as an extremely weak band. Variation of the solvent did not restore the peak intensity. A marked variation in the intensity of CN absorption from strong to undetectable in different solvents and with the incorporation of certain substituents is well documented: Bellamy, L. J. In The Infrared Spectra of Complex Molecules, 3rd Ed.; Chapman and Hall: London and New York, 1975; Vol. 1, p 297.
    • (1975) The Infrared Spectra of Complex Molecules, 3rd Ed. , vol.1 , pp. 297
    • Bellamy, L.J.1
  • 55
    • 2242423055 scopus 로고    scopus 로고
    • note
    • 2 only. Given its very low concentration and the fact that it disappears on changing the solvent, concentration, or temperature, we cannot unambiguously assign this signal.
  • 59
    • 2242463440 scopus 로고    scopus 로고
    • note
    • The free radical concentration in the solid state was estimated at 298 K by spin counting experiment to be ca. 15%, as a result of antiferromagnetic interaction between neighboring fluorene moieties. Lowering of the observed spin number (in respect to the theoretical value) is typical for many radical ion salts, e.g., ref 3b.
  • 60
    • 2242493015 scopus 로고    scopus 로고
    • note
    • +, precludes observation of the smaller couplings.
  • 62
    • 2242436606 scopus 로고    scopus 로고
    • note
    • Fast scanning of the potential with continuous recording of the spectra was employed as a practically achievable alternative to time-resolved pulse SEEPR.
  • 63
    • 0000402838 scopus 로고    scopus 로고
    • Reference 16d
    • Although formation of cation radical also yields one aromatic dithiolium ring, the largest gain of aromaticity occurs on transition from cation radical (which essentially preserves the geometry of the neutral species) to fully aromatic dication: (a) Reference 16d. (b) Martín, N.; Sánchez, L.; Seoane, C.; Ortí, E.; Viruela, P. M.; Viruela, R. J. Org. Chem. 1998, 63, 1268-1279.
  • 64
    • 0000402838 scopus 로고    scopus 로고
    • Although formation of cation radical also yields one aromatic dithiolium ring, the largest gain of aromaticity occurs on transition from cation radical (which essentially preserves the geometry of the neutral species) to fully aromatic dication: (a) Reference 16d. (b) Martín, N.; Sánchez, L.; Seoane, C.; Ortí, E.; Viruela, P. M.; Viruela, R. J. Org. Chem. 1998, 63, 1268-1279.
    • (1998) J. Org. Chem. , vol.63 , pp. 1268-1279
    • Martín, N.1    Sánchez, L.2    Seoane, C.3    Ortí, E.4    Viruela, P.M.5    Viruela, R.6
  • 71
    • 2242421295 scopus 로고    scopus 로고
    • note
    • The low accuracy accompanying measurements of such weak bands does not exclude the possibility that intermolecular complexation may contribute to these absorption bands.
  • 72
    • 2242453601 scopus 로고    scopus 로고
    • note
    • 2+ does not absorb beyond 600 nm (ref 16d).
  • 73
    • 2242493014 scopus 로고    scopus 로고
    • Reference 21
    • All the known X-ray crystal structures of nitrofluorene-TTFs CTCs are neutral or have only partial charge transfer: (a) Reference 21.
  • 81
    • 2242472421 scopus 로고    scopus 로고
    • note
    • 2 (1.487(6) Å) (ref 16e).
  • 87
    • 2242420359 scopus 로고    scopus 로고
    • note
    • 2, mp 158-160 °C.
  • 88
    • 2242459857 scopus 로고    scopus 로고
    • note
    • Hydrolysis of compound 10 to fluorenone 9 on silica (which we have not observed for other fluorene-9-dicyanomethylene derivatives) does not allow chromatographic purification.
  • 89
    • 2242465197 scopus 로고    scopus 로고
    • note
    • 2 to elute all the compound.
  • 92
    • 0001405569 scopus 로고
    • in Russian
    • Procedure adapted from: Andrievskii, A. M.; Gorelik, M. V.; Avidon, S. V.; Al'tman, E. Sh. Russ. J. Org. Chem. 1993, 29, 1519-1524; Zh. Org. Khim. 1993, 29. 1828-1834 (in Russian).
    • (1993) Zh. Org. Khim. , vol.29 , pp. 1828-1834


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.