메뉴 건너뛰기




Volumn 15, Issue 2, 2009, Pages 506-516

Tetrathiafulvalene porphyrins

Author keywords

Electrochemistry; Electron transfer; Porphyrinoids; Supramolecular chemistry; Tetrathiafulvalenes

Indexed keywords

ABSORPTION SPECTROSCOPY; ELECTROCHEMISTRY; ELECTRON TRANSITIONS; EMISSION SPECTROSCOPY; FLUORESCENCE; MACROMOLECULES; OXIDATION; REDUCTION; SPECTROSCOPIC ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

EID: 58449123488     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801636     Document Type: Article
Times cited : (43)

References (107)
  • 1
    • 0003641908 scopus 로고    scopus 로고
    • Eds, K. M. Kadish, K. M. Smith, R. Guilard, Academic Press, San Diego
    • The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000.
    • (2000) The Porphyrin Handbook
  • 2
    • 0004155427 scopus 로고
    • 4th ed, W. H. Freeman, New York
    • L. Stryer, Biochemistry, 4th ed., W. H. Freeman, New York, 1995.
    • (1995) Biochemistry
    • Stryer, L.1
  • 20
    • 9344233567 scopus 로고    scopus 로고
    • Eds, J.-i. Yamada, T. Sugimoto, Kodansha, Tokyo
    • c) TTF Chemistry (Eds.: J.-i. Yamada, T. Sugimoto), Kodansha, Tokyo, 2004;
    • (2004) TTF Chemistry
  • 21
    • 10244244991 scopus 로고    scopus 로고
    • special issue on molecular conductors, Chem. Rev. 2004, 104, 4887-5782.
    • d) special issue on molecular conductors, Chem. Rev. 2004, 104, 4887-5782.
  • 24
    • 0035901526 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1372-1409;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1372-1409
  • 27
    • 58449124773 scopus 로고    scopus 로고
    • Organic Superconductors including Fullerenes (Eds.: J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geise, H. H. Wang, A. M. Kini, M.-.H. Wangbo), Prentice-Hall, Engelwood Cliffs, 1992, pp. 1-210.
    • Organic Superconductors including Fullerenes (Eds.: J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geise, H. H. Wang, A. M. Kini, M.-.H. Wangbo), Prentice-Hall, Engelwood Cliffs, 1992, pp. 1-210.
  • 29
    • 0035825125 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 224-227;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 224-227
  • 32
    • 0037434128 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 187-191;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 187-191
  • 37
    • 33750449309 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6848-6853;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6848-6853
  • 53
    • 0034753498 scopus 로고    scopus 로고
    • Only a few papers on molecular systems including both TTF and porphyrin units have been reported so far; see for instance: a P. A. Liddell, G. Kodis, L. de la Garza, J. L. Bahr, A. L. Moore, T. A. Moore, D. Gust, Helv. Chim. Acta 2001, 84, 2765-2783;
    • Only a few papers on molecular systems including both TTF and porphyrin units have been reported so far; see for instance: a) P. A. Liddell, G. Kodis, L. de la Garza, J. L. Bahr, A. L. Moore, T. A. Moore, D. Gust, Helv. Chim. Acta 2001, 84, 2765-2783;
  • 54
    • 0037213693 scopus 로고    scopus 로고
    • S.-i Sadaike, K. Takimiya, Y. Aso, T. Otsubo, Tetrahedron Lett. 2003, 44, 161-165;
    • b) S.-i Sadaike, K. Takimiya, Y. Aso, T. Otsubo, Tetrahedron Lett. 2003, 44, 161-165;
  • 61
    • 0035796763 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 2497-2500.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 2497-2500
  • 65
    • 58449134676 scopus 로고    scopus 로고
    • J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2000, 65, 5797-5805.
    • b) J. O. Jeppesen, K. Takimiya, F. Jensen, T. Brimert, K. Nielsen, N. Thorup, J. Becher, J. Org. Chem. 2000, 65, 5797-5805.
  • 76
    • 85168792111 scopus 로고    scopus 로고
    • S. W. Rhee, B. B. Park, Y. Do, J. Kim, Polyhedron 2000, 19, 1.961-1966;
    • f) S. W. Rhee, B. B. Park, Y. Do, J. Kim, Polyhedron 2000, 19, 1.961-1966;
  • 84
    • 58449095281 scopus 로고    scopus 로고
    • S. Cadamuro, I. Degani, R. .Fochi, A. Gatti, L. Piscopo, J. Chem. Soc. Perkin Trans. 1 1993, 2923-2943.
    • c) S. Cadamuro, I. Degani, R. .Fochi, A. Gatti, L. Piscopo, J. Chem. Soc. Perkin Trans. 1 1993, 2923-2943.
  • 85
    • 58449085890 scopus 로고    scopus 로고
    • Support for the proposed conversion of the monobenzoyl-MPTTF derivative 5 to the corresponding alcohol 6 came from the fact that a color change from orange to yellow was observed to take place during the reaction
    • Support for the proposed conversion of the monobenzoyl-MPTTF derivative 5 to the corresponding alcohol 6 came from the fact that a color change from orange to yellow was observed to take place during the reaction. In addition, TLC analysis revealed the presence of only one new product with a lower 7?, value than the starting material 6.
    • In addition, TLC analysis revealed the presence of only one new product with a lower 7?, value than the starting material , vol.6
  • 86
    • 58449084222 scopus 로고    scopus 로고
    • A 1H NMR spectroscopic examination carried out revealed spectral features consistent with the proposed complete reduction of the carbonyl group in 5 and the formation of the corresponding alcohol 6, can be handled for a few hours, significant decomposition is seen within one day
    • 1H NMR spectroscopic examination carried out revealed spectral features consistent with the proposed complete reduction of the carbonyl group in 5 and the formation of the corresponding alcohol 6. Although the alcohol 6 can be handled for a few hours, significant decomposition is seen within one day.
    • Although the alcohol , vol.6
  • 87
    • 58449086238 scopus 로고    scopus 로고
    • Some of us have previously reported (ref, 16, that the tetraTTF-annulated porphyrin 1 can be synthesized by stirring the MPTTF derivative 9, benzaldehyde, and a catalytic amount of p-toluenesulfoic acid (PTSA) in THF at RT for 18 h followed by DDQ oxidation. However, this method gives rise to a mixture of the neutral porphyrin 1 and the corresponding radical-cation porphyrin 1̇+ in a ratio of approximately 4:1. Unfortunately, in our hands this mixture proved impossible to separate by any means. The 1H NMR spectrum of this porphyrin mixture recorded in CDCl3 at 298 K featured only very broad peaks, an observation consistent with the presence of radicals or slow tumbling resulting from aggregation in solution. The radical-cation nature of the porphyrin mixture was confirmed (ref, 16, by quantitative electron paramagnetic resonance (EPR) spectroscopy. This porphyrin mixture 1 and 1̇, was is
    • ̇+) reflects the different physical properties of these ostensibly similar tetraTTF-porphyrin products. Note the high stability of both the neutral product 1, whose synthesis is detailed in this report, and the radical-cation porphyrin mixture prepared earlier. Unfortunately, as noted above, efforts to interconvert these ostensibly similar materials proved unsuccessful.
  • 88
    • 58449085332 scopus 로고    scopus 로고
    • A color change from deep-purple to yellow took place during the reduction, an observation that we take as indicative that the starting material 12 is being converted to the product 13. Based on TLC analysis, it was inferred that the diol 13 was unstable; therefore, no specific purification of this species was attempted.
    • A color change from deep-purple to yellow took place during the reduction, an observation that we take as indicative that the starting material 12 is being converted to the product 13. Based on TLC analysis, it was inferred that the diol 13 was unstable; therefore, no specific purification of this species was attempted.
  • 91
    • 0002315830 scopus 로고    scopus 로고
    • b) T. D. Lash, Chem. Eur. J. 1996, 10, 1197-1200;
    • (1996) Chem. Eur. J , vol.10 , pp. 1197-1200
    • Lash, T.D.1
  • 98
    • 58449132953 scopus 로고    scopus 로고
    • Further support for this conclusion comes from the finding that no radical signals could be seen using conventional EPR spectroscopy
    • Further support for this conclusion comes from the finding that no radical signals could be seen using conventional EPR spectroscopy.
  • 99
    • 58449129199 scopus 로고    scopus 로고
    • 1HNMR spectrum of a sample of 1 obtained using the previously published procedure (ref. [16]) featured broad lines.
    • 1HNMR spectrum of a sample of 1 obtained using the previously published procedure (ref. [16]) featured broad lines.
  • 100
    • 58449086504 scopus 로고    scopus 로고
    • X-ray crystal-structure determination of 3: Crystals of the bisTTF-porphyrin 3, suitable for X-ray diffraction, were grown by slow diffusion of a MeOH layer into a CH2Cl2 solution containing 3. Crystallographic data: C83H92C 16N4S12, Mr, 1743.03, triclinic, P1̄, dark-brown plates, crystal size, 0.42×0.40×0.06 mm3, Z=2, a, 13.3526(2, b, 16.2106(3, c=21.3553(4) Å, α, 93.017(1, β= 92.291(1, γ, 111.631(1)°, V=4282.16(13)Å3, T=153K, λ, 0.71073, ρcalcd, 1.352 g cm-3, μ(MoKα, 0.539 mm-1, F(000, 1824, θ range=2.94 to 27.50°, reflections, 3091.0, parameters= 19182, R1 [I>2σI, 0.0891, wR2=0.1437, GOF=1.836. The data were collected by using a Noni
    • 1/2, in which n is the number of reflections and p is the number of refined parameters. The data were checked for secondary extinction effects, but no correction was applied. Neutral atom-scattering factors and values used to calculate the linear-absorption co-efficient are from the International Tables for X-ray Crystallography: International Tables for X-ray Crystallography, Vol. C, Tables 4.2.6.8 and 6.1.1.4 (Ed.: A. J. C. Wilson), Kluwer Academic Press, Boston, 1992. CCDC 697641 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
  • 105
    • 58449135879 scopus 로고    scopus 로고
    • ̇+→ TTF) through the addition of chemical reductants proved unsuccessful.
    • ̇+→ TTF) through the addition of chemical reductants proved unsuccessful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.