메뉴 건너뛰기




Volumn 39, Issue 4, 2000, Pages 809-812

A redox-controlled molecular switch based on the reversible C-C bond formation in octamethoxytetraphenylene

Author keywords

Cyclic voltammetry; Electrochemistry; Molecular devices; Radicals

Indexed keywords

BENZENE DERIVATIVE; CARBON;

EID: 0034681497     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000218)39:4<809::AID-ANIE809>3.0.CO;2-6     Document Type: Article
Times cited : (68)

References (44)
  • 7
    • 0001991013 scopus 로고
    • Eds.: M. C. Petty, M. R. Bryce, D. Bloor, Edward Arnold, London
    • c) D. K. Das-Gupta in Introduction to Molecular Electronics (Eds.: M. C. Petty, M. R. Bryce, D. Bloor), Edward Arnold, London, 1995, pp. 47-71;
    • (1995) Introduction to Molecular Electronics , pp. 47-71
    • Das-Gupta, D.K.1
  • 21
    • 33747552392 scopus 로고    scopus 로고
    • note
    • The disk-shaped hexamethoxytriphenylene is planar and has been extensively studied owing to its liquid-crystalline properties. However, its higher homologue octamethoxytetraphenylene (OMT) is heretofore unknown.
  • 22
    • 33747524098 scopus 로고    scopus 로고
    • note
    • Note that the dark-red solution obtained upon electrooxidation of OMT was EPR-silent. Either an electroreduction or a treatment of the red-colored solution with zinc dust led to the recovery of neutral OMT in quantitative yield.
  • 23
    • 33751156326 scopus 로고
    • 0 = 1.1-1.3 V vs. SCE) are useful one-electron oxidants, see: R. Rathore, J. K. Kochi, J. Org. Chem. 1994, 60, 4399.
    • (1994) J. Org. Chem. , vol.60 , pp. 4399
    • Rathore, R.1    Kochi, J.K.2
  • 27
    • 33747544339 scopus 로고    scopus 로고
    • note
    • The redox stoichiometry in Equation (2) is further confirmed by coulometry at a constant potential of 1.25 V (vs. SCE) in dichloromethane (containing 0.2 M tetra-n-butylammonium hexafluorophosphate as supporting electrolyte) at 0°C.
  • 28
    • 33747562836 scopus 로고    scopus 로고
    • The identity of liberated NO gas is confirmed by UV/Vis and IR spectroscopy, see refs. [8, 9]
    • The identity of liberated NO gas is confirmed by UV/Vis and IR spectroscopy, see refs. [8, 9].
  • 29
    • 0031587455 scopus 로고    scopus 로고
    • 0 = 2.15 V vs. SCE) and readily oxidizes a variety of aromatic donors to their radical cations, see: R. Rathore, S. M. Hubig, J. K. Kochi, J. Am. Chem. Soc. 1997, 119, 11 468.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11468
    • Rathore, R.1    Hubig, S.M.2    Kochi, J.K.3
  • 31
    • 33747577595 scopus 로고    scopus 로고
    • Methoxy groups are omitted for the sake of clarity
    • Methoxy groups are omitted for the sake of clarity.
  • 32
    • 33747574236 scopus 로고    scopus 로고
    • note
    • 2+ around C11 and C31 are: C12-C11-C31 105.2, C12-C11-C42112.6, C16-C11-C12114.7, C16-C11-C42 106.4, C16-C11-C31 116.8, C42-C11-C31 100.5, C32-C31-C11 105.1, C32-C31-C22 106.5, C36-C31-C32 114.1, C36-C31-C11 117.8, C36-C31-C22 110.7, C11-C31-C22 101.3.
  • 36
    • 0024034437 scopus 로고
    • D. K. Gosser, P. H. Rieger, Anal. Chem. 1988, 60, 1159. A Fortran listing or PC version (Turbo-Pascal 5) of the program is available upon request from D. K. Gosser, City College, City University of New York. We thank Professor Gosser for providing us a copy of the PC version of the program.
    • (1988) Anal. Chem. , vol.60 , pp. 1159
    • Gosser, D.K.1    Rieger, P.H.2
  • 38
    • 0002448959 scopus 로고
    • and references therein
    • The distonic radical cations have ample literature precedent in the synthesis of a variety of biaryls, see : O. Hammerich, V. D. Parker, Adv. Phys. Org. Chem. 1984, 20, 55, and references therein.
    • (1984) Adv. Phys. Org. Chem. , vol.20 , pp. 55
    • Hammerich, O.1    Parker, V.D.2
  • 39
    • 0003907177 scopus 로고
    • Elsevier, New York
    • -1 based on time-resolved absorption measurements upon diffusional electron-transfer quenching of photoexcited chloranil, see ref. [14]. Thus, the transient spectrum obtained 1 μs after laser excitation (10 ns) of chloranil (8 mM) in the presence of OMT (10 mM) shows an absorption band at 450 nm with a shoulder at 420 nm, characteristic of a chloranil radical anion, as well as a band at 370 nm and a weak (broad) absorption at about 660 nm. The latter two absorptions are tentatively assigned to the spectrum of the distonic radical cation since it lacks the characteristic absorption wavelengths of the radical cations of either the dimethoxybenzenes or the methoxylated biphenyls (see: T. Shida, Electronic Absorption Spectra, Elsevier, New York, 1988).
    • (1988) Electronic Absorption Spectra
    • Shida, T.1
  • 40
    • 0002448959 scopus 로고
    • Cyclohexadienyl-type radicals are known to undergo oxidation at circa 0 V (vs. SCE), see: O. Hammerich, V. D. Parker, Adv. Phys. Org. Chem. 1984, 20, 55.
    • (1984) Adv. Phys. Org. Chem. , vol.20 , pp. 55
    • Hammerich, O.1    Parker, V.D.2
  • 44
    • 33747542245 scopus 로고
    • University of Göttingen (Germany)
    • G. M. Sheldrick, SHELSX-S6, University of Göttingen (Germany), 1986.
    • (1986) SHELSX-S6
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.