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Volumn 121, Issue 37, 1999, Pages 8434-8442

The class II/III transition in triarylamine redox systems

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; BENZENE DERIVATIVE; CATION; N,N,N',N' TETRAMETHYL 1,4 PHENYLENEDIAMINE; RADICAL;

EID: 0043125156     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991264s     Document Type: Article
Times cited : (517)

References (101)
  • 2
    • 0345330736 scopus 로고
    • Chem. Rev. 1992, 92, 369. This issue is devoted to ET processes in biologically relevant systems.
    • (1992) Chem. Rev. , vol.92 , pp. 369
  • 60
    • 0002769275 scopus 로고    scopus 로고
    • Dietrich, J., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany
    • Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Dietrich, J., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 203.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203
    • Sonogashira, K.1
  • 63
    • 0344896109 scopus 로고    scopus 로고
    • note
    • The redox potentials of 1 are too close to the accessible electrochemical window of DMSO to allow accurate measurements.
  • 68
    • 0039704429 scopus 로고
    • Electrochemical and spectroelectrochemical data for the related tetraphenyl-p-phenylenediamine radical cation can be found in (a) Cauquis, G.; Serve, D. Anal. Chem. 1972, 44, 2222. (b) Moll, T.; Heinze, J. Synth. Metals 1993, 55-57, 1521.
    • (1972) Anal. Chem. , vol.44 , pp. 2222
    • Cauquis, G.1    Serve, D.2
  • 69
    • 43949167334 scopus 로고
    • Electrochemical and spectroelectrochemical data for the related tetraphenyl-p-phenylenediamine radical cation can be found in (a) Cauquis, G.; Serve, D. Anal. Chem. 1972, 44, 2222. (b) Moll, T.; Heinze, J. Synth. Metals 1993, 55-57, 1521.
    • (1993) J. Synth. Metals , vol.55-57 , pp. 1521
    • Moll, T.1    Heinze2
  • 70
    • 0344033181 scopus 로고    scopus 로고
    • note
    • We are especially grateful to Prof. S. Nelsen, who disvovered this aspect parallel to us, for a thorough and enlightening discussion on this point.
  • 74
    • 0344464260 scopus 로고    scopus 로고
    • note
    • max. This results in a ΔG* that is ∼10% smaller than the one given in Table 3. Thus, the ΔG* values in Table 3 may be regarded as upper bounds.
  • 76
    • 0344464261 scopus 로고    scopus 로고
    • private communication
    • Nelsen, S. F. private communication.
    • Nelsen, S.F.1
  • 77
    • 0344033184 scopus 로고    scopus 로고
    • note
    • NN in the present paper.
  • 78
    • 0344033182 scopus 로고    scopus 로고
    • note
    • + merely represents a mean ET distance.
  • 80
    • 84985450224 scopus 로고
    • (b) Nelsen, S. F.; Yunta, M. J. R. J. Phys. Org. Chem. 1994, 7, 55. In principle, one should not speak of IV-CT bands in delocalized class III systems where neither charge is transferred nor two different valences are present. Although incorrect, we retain using this term because of the lack of a better one.
    • (1994) J. Phys. Org. Chem. , vol.7 , pp. 55
    • Nelsen, S.F.1    Yunta, M.J.R.2
  • 83
    • 0344033180 scopus 로고    scopus 로고
    • note
    • See ref 19q where values from ref 33a were used for obtaining β.
  • 84
    • 0013449107 scopus 로고
    • There have been many attempts in the literature to correlate redox potential splittings with spectroscopic data, see, for example, (a) de la Rosa, R.; Chang, P. J.; Salaymeh, F.; Curtis, J. C. Inorg. Chem. 1985, 24, 4231. (b) Dong, Y.; Hupp, J. T. Inorg. Chem. 1992, 31, 3170. (c) Evans, C. E. B.; Naklicki, M. L.; Rezvani, A. R.; White, C. A.; Kondratiev, V. V.; Crutchley, R. J. Am. Chem. Soc. 1998, 120, 13096. Crutchley et al. did not find a linear correlation between electrochemically determined resonance energies and energies derived from a Hush analysis for a series of transition metal complexes. However, the complexes were studied in different solvents and were not a homologous series.
    • (1985) Inorg. Chem. , vol.24 , pp. 4231
    • De La Rosa, R.1    Chang, P.J.2    Salaymeh, F.3    Curtis, J.C.4
  • 85
    • 0001496757 scopus 로고
    • There have been many attempts in the literature to correlate redox potential splittings with spectroscopic data, see, for example, (a) de la Rosa, R.; Chang, P. J.; Salaymeh, F.; Curtis, J. C. Inorg. Chem. 1985, 24, 4231. (b) Dong, Y.; Hupp, J. T. Inorg. Chem. 1992, 31, 3170. (c) Evans, C. E. B.; Naklicki, M. L.; Rezvani, A. R.; White, C. A.; Kondratiev, V. V.; Crutchley, R. J. Am. Chem. Soc. 1998, 120, 13096. Crutchley et al. did not find a linear correlation between electrochemically determined resonance energies and energies derived from a Hush analysis for a series of transition metal complexes. However, the complexes were studied in different solvents and were not a homologous series.
    • (1992) Inorg. Chem. , vol.31 , pp. 3170
    • Dong, Y.1    Hupp, J.T.2
  • 86
    • 0032561766 scopus 로고    scopus 로고
    • There have been many attempts in the literature to correlate redox potential splittings with spectroscopic data, see, for example, (a) de la Rosa, R.; Chang, P. J.; Salaymeh, F.; Curtis, J. C. Inorg. Chem. 1985, 24, 4231. (b) Dong, Y.; Hupp, J. T. Inorg. Chem. 1992, 31, 3170. (c) Evans, C. E. B.; Naklicki, M. L.; Rezvani, A. R.; White, C. A.; Kondratiev, V. V.; Crutchley, R. J. Am. Chem. Soc. 1998, 120, 13096. Crutchley et al. did not find a linear correlation between electrochemically determined resonance energies and energies derived from a Hush analysis for a series of transition metal complexes. However, the complexes were studied in different solvents and were not a homologous series.
    • (1998) Am. Chem. Soc. , vol.120 , pp. 13096
    • Evans, C.E.B.1    Naklicki, M.L.2    Rezvani, A.R.3    White, C.A.4    Kondratiev, V.V.5    Crutchley, R.J.6
  • 91
    • 0344464255 scopus 로고    scopus 로고
    • note
    • + yielded an asymmetric charge distribution even when the geometry was restricted to be symmetric. Therefore, this electronic structure is not the correct transition state on the ET coordinate. As there is no way to force the wave function to be symmetric using Mopac97, we used the geometry of the neutral species for obtaining V.
  • 92
    • 0345327099 scopus 로고    scopus 로고
    • note
    • For a discussion of the influence of torsional angles on the electronic coupling in biphenyl systems, see ref 19q.
  • 94
    • 0344033176 scopus 로고    scopus 로고
    • note
    • max(DMSO).
  • 101
    • 0344464254 scopus 로고    scopus 로고
    • Fujitsu Inc., Japan
    • Mopac97, Fujitsu Inc., Japan, 1997.
    • (1997) Mopac97


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.