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Volumn 122, Issue 24, 2000, Pages 5748-5757

'N-fused porphyrin': A new tetrapyrrolic porphyrinoid with a fused tri- pentacyclic ring

Author keywords

[No Author keywords available]

Indexed keywords

BASE; CHLOROETHANE; MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; PORPHYRIN DERIVATIVE; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0000739917     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000148i     Document Type: Article
Times cited : (144)

References (54)
  • 1
    • 0343301006 scopus 로고
    • Smith, K. M., Ed.; Elsevier: Amsterdam, Chapter 18
    • For overviews of porphyrin analogues, see: (a) Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; Chapter 18. (b) Grigg, R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Chapter 10. (c) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins; Tetrahedron Organic Chemistry Series, Vol. 15; Pergamon: New York, 1997. (d) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2.
    • (1975) Porphyrins and Metalloporphyrins
    • Johnson, A.W.1
  • 2
    • 0343736523 scopus 로고
    • Dolphin, D., Ed.; Academic Press: New York, Chapter 10
    • For overviews of porphyrin analogues, see: (a) Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; Chapter 18. (b) Grigg, R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Chapter 10. (c) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins; Tetrahedron Organic Chemistry Series, Vol. 15; Pergamon: New York, 1997. (d) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2.
    • (1978) The Porphyrins
    • Grigg, R.1
  • 3
    • 0002113233 scopus 로고    scopus 로고
    • Expanded, Contracted & Isomeric Porphyrins
    • Pergamon: New York
    • For overviews of porphyrin analogues, see: (a) Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; Chapter 18. (b) Grigg, R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Chapter 10. (c) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins; Tetrahedron Organic Chemistry Series, Vol. 15; Pergamon: New York, 1997. (d) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2.
    • (1997) Tetrahedron Organic Chemistry Series , vol.15
    • Sessler, J.L.1    Weghorn, S.J.2
  • 4
    • 0003641908 scopus 로고    scopus 로고
    • Academic Press: San Diego
    • For overviews of porphyrin analogues, see: (a) Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, 1975; Chapter 18. (b) Grigg, R. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Chapter 10. (c) Sessler, J. L.; Weghorn, S. J. Expanded, Contracted & Isomeric Porphyrins; Tetrahedron Organic Chemistry Series, Vol. 15; Pergamon: New York, 1997. (d) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999; Vol. 2.
    • (1999) The Porphyrin Handbook , vol.2
    • Kadish, K.M.1    Smith, K.M.2    Guilard, R.3
  • 12
    • 0342431408 scopus 로고    scopus 로고
    • note
    • For convenience, the same compound numbers with "prime" symbol were used for tolyl derivatives, e.g., 3a (Ar = phenyl) and 3a′ (Ar = tolyl).
  • 17
  • 22
    • 0003641908 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds; Academic Press: San Diego, Chapter 14
    • (e) Latos-Grażyński, L. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds; Academic Press: San Diego, 1999; Vol. 2, Chapter 14.
    • (1999) The Porphyrin Handbook , vol.2
    • Latos-Grazyński, L.1
  • 32
    • 0343736514 scopus 로고    scopus 로고
    • Unpublished data
    • Iodo derivative 2d was too unstable to measure the absorption spectrum correctly, but the corresponding anisyl-substituted NCPs were stable, and they gave a similar tendency; 443.0 (FB), 453.8 (Cl), 457.8 (Br), and 465.0 nm (I). Furuta, H.; Tsuruoka, S. Unpublished data.
    • Furuta, H.1    Tsuruoka, S.2
  • 33
    • 0342431398 scopus 로고    scopus 로고
    • note
    • 11
  • 35
    • 0343736512 scopus 로고    scopus 로고
    • note
    • β bond length was 1.341 Å. See ref 14.
  • 36
    • 0004133516 scopus 로고    scopus 로고
    • Gaussian, Inc.: Pittsburgh, PA
    • All calculations were performed with: Gaussian 98W/DFT program (Rev. A.7); Gaussian, Inc.: Pittsburgh, PA, 1998.
    • (1998) Gaussian 98W/DFT Program (Rev. A.7)
  • 41
    • 0342865942 scopus 로고    scopus 로고
    • note
    • 5 derivatives of 4b and Sb were used for the measurements. See Supporting Information.
  • 43
    • 0002802707 scopus 로고
    • By the ab initio calculations the electron withdrawing substituents of a hydrogen acceptor molecule were shown to weaken the hydrogen bondings ability. See: (a) Del Bene, J. E.; Person, W. B.; Szczepaniak, K. Chem. Phys. Lett. 1995, 247, 89-94. (b) Del Bene, J. E.; Person, W. B.; Szczepaniak, K. Mol. Phys. 1996, 89, 47-59.
    • (1995) Chem. Phys. Lett. , vol.247 , pp. 89-94
    • Del Bene, J.E.1    Person, W.B.2    Szczepaniak, K.3
  • 44
    • 0001769122 scopus 로고    scopus 로고
    • By the ab initio calculations the electron withdrawing substituents of a hydrogen acceptor molecule were shown to weaken the hydrogen bondings ability. See: (a) Del Bene, J. E.; Person, W. B.; Szczepaniak, K. Chem. Phys. Lett. 1995, 247, 89-94. (b) Del Bene, J. E.; Person, W. B.; Szczepaniak, K. Mol. Phys. 1996, 89, 47-59.
    • (1996) Mol. Phys. , vol.89 , pp. 47-59
    • Del Bene, J.E.1    Person, W.B.2    Szczepaniak, K.3
  • 45
    • 0343300989 scopus 로고    scopus 로고
    • The UV/vis spectra for 4a′, 4b, 4c, 5b, and 5e are shown in Supporting Information
    • The UV/vis spectra for 4a′, 4b, 4c, 5b, and 5e are shown in Supporting Information.
  • 47
    • 0342865939 scopus 로고    scopus 로고
    • Fujitsu: Tokyo
    • Calculation was performed using: WinMOPAC program, version 2.0; Fujitsu: Tokyo, 1998. HOMO and LUMO orbitals of NFP are shown in Supporting Information.
    • (1998) WinMOPAC Program, Version 2.0
  • 53
    • 0342431390 scopus 로고    scopus 로고
    • note
    • 7 at room temperature.
  • 54
    • 0342431389 scopus 로고    scopus 로고
    • March, Kyoto, Japan
    • NMR and UV/vis changes of the NH tautomer of NCPs were reported: Japanese Chemical Society, annual meeting, 1998, March, Kyoto, Japan. Full accounts of the NH tautomerism for NCPs will be reported in due course.
    • (1998) Japanese Chemical Society, Annual Meeting


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.