메뉴 건너뛰기




Volumn 70, Issue 3, 2005, Pages 874-891

Synthesis of isomeric angularly annealed dinaphthoporphyrin systems: Examination of the relative positioning and orientation of ring fusion as factors influencing the porphyrin chromophore

Author keywords

[No Author keywords available]

Indexed keywords

ANNEALING; CHEMICAL ANALYSIS; CHROMOPHORES; CONDENSATION; DEHYDROGENATION; FUSION REACTIONS; ISOMERS; SOLUBILITY; SYNTHESIS (CHEMICAL);

EID: 13244299135     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040269r     Document Type: Article
Times cited : (39)

References (102)
  • 1
    • 0001004194 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego
    • Lash, T. D. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 2, pp 125-199.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 125-199
    • Lash, T.D.1
  • 5
    • 0000303285 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego
    • (a) Pandey, R. K.; Zheng, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 6, pp 157-230.
    • (2000) The Porphyrin Handbook , vol.6 , pp. 157-230
    • Pandey, R.K.1    Zheng, G.2
  • 24
    • 0000684776 scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (1979) J. Gen. Chem. USSR , vol.49 , pp. 2467
    • Kopranenkov, V.N.1    Vorotnikov, A.M.2    Luk'yanets, E.A.3
  • 25
    • 84984379842 scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (1988) Chem. Ber. , vol.121 , pp. 1601
    • Rein, M.1    Hanack, M.2
  • 26
    • 0002149271 scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (1993) Chem. Phys. Lett. , vol.205 , pp. 51
    • Kobayashi, N.1    Nevin, W.A.2    Mizunuma, S.3    Awaji, H.4    Yamaguchi, M.5
  • 27
    • 0030859953 scopus 로고    scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (1997) Chem. Commun. , pp. 1199
    • Tomé, A.C.1    Lacerdo, P.S.S.2    Neves, M.G.P.M.S.3    Cavaleiro, J.A.S.4
  • 28
    • 0034616795 scopus 로고    scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (2000) Chem. Commun. , pp. 893
    • Ito, S.1    Ochi, N.2    Uno, H.3    Murashima, T.4    Ono, N.5
  • 29
    • 0141566399 scopus 로고    scopus 로고
    • For examples of naphtho[2,3-b]porphyrins and related linearly annealed systems, see: (a) Kopranenkov, V. N.; Vorotnikov, A. M.; Luk'yanets, E. A. J. Gen. Chem. USSR 1979, 49, 2467. (b) Rein, M.; Hanack, M. Chem. Ber. 1988, 121, 1601. (c) Kobayashi, N.; Nevin, W. A.; Mizunuma, S.; Awaji, H.; Yamaguchi, M. Chem. Phys. Lett. 1993, 205, 51. (d) Tomé, A. C.; Lacerdo, P. S. S.; Neves, M. G. P. M. S.; Cavaleiro, J. A. S. Chem. Commun. 1997, 1199. (e) Ito, S.; Ochi, N.; Uno, H.; Murashima, T.; Ono, N. Chem. Commun. 2000, 893. (f) Finikova, O. S.; Cheprakov, A. V.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2003, 68, 7517.
    • (2003) J. Org. Chem. , vol.68 , pp. 7517
    • Finikova, O.S.1    Cheprakov, A.V.2    Carroll, P.J.3    Vinogradov, S.A.4
  • 46
    • 13244276096 scopus 로고
    • Abstract No. 45
    • These results were presented, in part, at the following meetings: 85th Annual Meeting of the Illinois State Academy of Science, Springfield, IL, Oct 1992 (Roper, T. J.; Denny, C. P.; Lash, T. D. Trans. Illinois State Acad. Sci. 1992, 85 (Suppl.), 46, Abstract No. 45); 207th National ACS Meeting, San Diego, CA, March 1994 (Lash, T. D.; Roper, T. J.; Novak, B. H.; Lin, Y. Book of Abstracts, ORGN 154); 34th Midwest Regional ACS Meeting, Quincy, IL, Oct. 1999 (Manley, J. M.; Lash, T. D. Program and Abstracts, Abstract No. 164); 219th National ACS Meeting, San Francisco, CA, March 2000 (Manley, J. M.; Lash, T. D. Book of Abstracts, ORGN 357).
    • (1992) Trans. Illinois State Acad. Sci. , vol.85 , Issue.SUPPL. , pp. 46
    • Roper, T.J.1    Denny, C.P.2    Lash, T.D.3
  • 47
    • 13244277187 scopus 로고
    • San Diego, CA, March Book of Abstracts, ORGN 154
    • These results were presented, in part, at the following meetings: 85th Annual Meeting of the Illinois State Academy of Science, Springfield, IL, Oct 1992 (Roper, T. J.; Denny, C. P.; Lash, T. D. Trans. Illinois State Acad. Sci. 1992, 85 (Suppl.), 46, Abstract No. 45); 207th National ACS Meeting, San Diego, CA, March 1994 (Lash, T. D.; Roper, T. J.; Novak, B. H.; Lin, Y. Book of Abstracts, ORGN 154); 34th Midwest Regional ACS Meeting, Quincy, IL, Oct. 1999 (Manley, J. M.; Lash, T. D. Program and Abstracts, Abstract No. 164); 219th National ACS Meeting, San Francisco, CA, March 2000 (Manley, J. M.; Lash, T. D. Book of Abstracts, ORGN 357).
    • (1994) 207th National ACS Meeting
    • Lash, T.D.1    Roper, T.J.2    Novak, B.H.3    Lin, Y.4
  • 48
    • 13244265220 scopus 로고    scopus 로고
    • Quincy, IL, Oct. Program and Abstracts, Abstract No. 164
    • These results were presented, in part, at the following meetings: 85th Annual Meeting of the Illinois State Academy of Science, Springfield, IL, Oct 1992 (Roper, T. J.; Denny, C. P.; Lash, T. D. Trans. Illinois State Acad. Sci. 1992, 85 (Suppl.), 46, Abstract No. 45); 207th National ACS Meeting, San Diego, CA, March 1994 (Lash, T. D.; Roper, T. J.; Novak, B. H.; Lin, Y. Book of Abstracts, ORGN 154); 34th Midwest Regional ACS Meeting, Quincy, IL, Oct. 1999 (Manley, J. M.; Lash, T. D. Program and Abstracts, Abstract No. 164); 219th National ACS Meeting, San Francisco, CA, March 2000 (Manley, J. M.; Lash, T. D. Book of Abstracts, ORGN 357).
    • (1999) 34th Midwest Regional ACS Meeting
    • Manley, J.M.1    Lash, T.D.2
  • 49
    • 13244296566 scopus 로고    scopus 로고
    • San Francisco, CA, March Book of Abstracts, ORGN 357
    • These results were presented, in part, at the following meetings: 85th Annual Meeting of the Illinois State Academy of Science, Springfield, IL, Oct 1992 (Roper, T. J.; Denny, C. P.; Lash, T. D. Trans. Illinois State Acad. Sci. 1992, 85 (Suppl.), 46, Abstract No. 45); 207th National ACS Meeting, San Diego, CA, March 1994 (Lash, T. D.; Roper, T. J.; Novak, B. H.; Lin, Y. Book of Abstracts, ORGN 154); 34th Midwest Regional ACS Meeting, Quincy, IL, Oct. 1999 (Manley, J. M.; Lash, T. D. Program and Abstracts, Abstract No. 164); 219th National ACS Meeting, San Francisco, CA, March 2000 (Manley, J. M.; Lash, T. D. Book of Abstracts, ORGN 357).
    • (2000) 219th National ACS Meeting
    • Manley, J.M.1    Lash, T.D.2
  • 50
    • 13244253388 scopus 로고    scopus 로고
    • M.S. Thesis, Illinois State University
    • Results taken, in part, from: Manley, J. M. M.S. Thesis, Illinois State University, 2001.
    • (2001)
    • Manley, J.M.1
  • 51
    • 13244260429 scopus 로고    scopus 로고
    • note
    • Series A-E were assigned in the order that they were synthesized, which also provides the most logical sequence for discussing the syntheses of these five dinaphthoporphyrin systems.
  • 52
    • 0002226421 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego
    • For recent reviews on porphyrin synthesis, see: (a) Smith, K. M. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, pp 1-43. (b) Smith, K. M. J. Porphyrins Phthalocyanines 2000, 4, 319-324.
    • (2000) The Porphyrin Handbook , vol.1 , pp. 1-43
    • Smith, K.M.1
  • 53
    • 0033667991 scopus 로고    scopus 로고
    • For recent reviews on porphyrin synthesis, see: (a) Smith, K. M. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, pp 1-43. (b) Smith, K. M. J. Porphyrins Phthalocyanines 2000, 4, 319-324.
    • (2000) J. Porphyrins Phthalocyanines , vol.4 , pp. 319-324
    • Smith, K.M.1
  • 55
    • 37049063355 scopus 로고
    • 8a dehydrogenation of a tetracyclohexenotetraazaporphyrin to phthalocyanine (and/or intermediary species) with DDQ in o-dichlorobenzene had been reported many years earlier. See: Ficken, G. E.; Linstead, R. P.; Stephen, E.; Whalley, M. J. Chem. Soc. 1958, 3879. See also: Ficken, G. E.; Linstead, R. P. J. Chem. Soc. 1952, 4846.
    • (1958) J. Chem. Soc. , pp. 3879
    • Ficken, G.E.1    Linstead, R.P.2    Stephen, E.3    Whalley, M.4
  • 56
    • 0007876439 scopus 로고
    • 8a dehydrogenation of a tetracyclohexenotetraazaporphyrin to phthalocyanine (and/or intermediary species) with DDQ in o-dichlorobenzene had been reported many years earlier. See: Ficken, G. E.; Linstead, R. P.; Stephen, E.; Whalley, M. J. Chem. Soc. 1958, 3879. See also: Ficken, G. E.; Linstead, R. P. J. Chem. Soc. 1952, 4846.
    • (1952) J. Chem. Soc. , pp. 4846
    • Ficken, G.E.1    Linstead, R.P.2
  • 57
    • 0000755805 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego
    • Smith, K. M. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, pp 119-148.
    • (2000) The Porphyrin Handbook , vol.1 , pp. 119-148
    • Smith, K.M.1
  • 91
    • 0003026147 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego
    • For a recent review on the NMR properties of porphyrins, see: Medforth, C. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 5, pp 1-80.
    • (2000) The Porphyrin Handbook , vol.5 , pp. 1-80
    • Medforth, C.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.