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Volumn 36, Issue 15, 1997, Pages 1651-1654

Octaethylhemiporphycene: Synthesis, Molecular Structure, and Photophysics

Author keywords

Chirality; N ligands; Photophysics; Porphyrinoids; Synthesis design

Indexed keywords


EID: 0030854239     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199716511     Document Type: Article
Times cited : (89)

References (49)
  • 1
    • 0000100569 scopus 로고
    • J. Waluk, J. Michl, J. Org. Chem. 1991, 56, 2729; J. L. Sessler, Angew. Chem. 1994, 106, 1410; Angew. Chem. Int. Ed. Engl. 1994, 33, 1348.
    • (1991) J. Org. Chem. , vol.56 , pp. 2729
    • Waluk, J.1    Michl, J.2
  • 2
    • 0001293770 scopus 로고
    • J. Waluk, J. Michl, J. Org. Chem. 1991, 56, 2729; J. L. Sessler, Angew. Chem. 1994, 106, 1410; Angew. Chem. Int. Ed. Engl. 1994, 33, 1348.
    • (1994) Angew. Chem. , vol.106 , pp. 1410
    • Sessler, J.L.1
  • 3
    • 33748219260 scopus 로고
    • J. Waluk, J. Michl, J. Org. Chem. 1991, 56, 2729; J. L. Sessler, Angew. Chem. 1994, 106, 1410; Angew. Chem. Int. Ed. Engl. 1994, 33, 1348.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1348
  • 4
    • 0000742655 scopus 로고
    • E. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262; Angew. Chem. Int. Ed. Engl. 1986, 25, 257; E. Vogel, Pure Appl. Chem. 1990, 62, 557; ibid. 1993, 63, 143; ibid. 1996, 68, 1355.
    • (1986) Angew. Chem. , vol.98 , pp. 262
    • Vogel, E.1    Köcher, M.2    Schmickler, H.3    Lex, J.4
  • 5
    • 0022625125 scopus 로고
    • E. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262; Angew. Chem. Int. Ed. Engl. 1986, 25, 257; E. Vogel, Pure Appl. Chem. 1990, 62, 557; ibid. 1993, 63, 143; ibid. 1996, 68, 1355.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 257
  • 6
    • 0001760791 scopus 로고
    • E. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262; Angew. Chem. Int. Ed. Engl. 1986, 25, 257; E. Vogel, Pure Appl. Chem. 1990, 62, 557; ibid. 1993, 63, 143; ibid. 1996, 68, 1355.
    • (1990) Pure Appl. Chem. , vol.62 , pp. 557
    • Vogel, E.1
  • 7
    • 0642275493 scopus 로고
    • E. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262; Angew. Chem. Int. Ed. Engl. 1986, 25, 257; E. Vogel, Pure Appl. Chem. 1990, 62, 557; ibid. 1993, 63, 143; ibid. 1996, 68, 1355.
    • (1993) Pure Appl. Chem. , vol.63 , pp. 143
  • 8
    • 0000729629 scopus 로고    scopus 로고
    • E. Vogel, M. Köcher, H. Schmickler, J. Lex, Angew. Chem. 1986, 98, 262; Angew. Chem. Int. Ed. Engl. 1986, 25, 257; E. Vogel, Pure Appl. Chem. 1990, 62, 557; ibid. 1993, 63, 143; ibid. 1996, 68, 1355.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 1355
  • 10
    • 33748233563 scopus 로고
    • E. Vogel, M. Bröring, J. Fink, D. Rosen, H. Schmickler, J. Lex, K. W. K. Chan, Y.-D. Wu, M. Nendel, D. A. Plattner, K. N. Houk, Angew. Chem. 1995, 107, 2705; Angew. Chem. Int. Ed. Engl. 1995, 34, 2511.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2511
  • 12
    • 33748240461 scopus 로고
    • a) J. L. Sessler, E. A. Brucker, S. J. Weghorn, M. Kisters, M. Schäfer, J. Lex, E. Vogel, Angew. Chem. 1994, 106, 2402; Angew. Chem. Int. Ed. Engl. 1994, 33, 2308;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2308
  • 14
    • 0000281064 scopus 로고
    • A French group reported a synthesis of corrphycene that was analogous to ours shortly after our publication [4a] appeared: M. A. Aukauloo, R. Guilard, New J. Chem. 1994, 18, 1205.
    • (1994) New J. Chem. , vol.18 , pp. 1205
    • Aukauloo, M.A.1    Guilard, R.2
  • 15
    • 85044489319 scopus 로고    scopus 로고
    • An alternative corrphycene synthesis in which cyclization leading to the corrphycene framework is accomplished by an intramolecular Ullmann coupling of the corresponding α,ω-diiodotetrapyrrole: H. Falk, Q.-Q. Chen, Monatsh. Chem. 1996, 127, 69.
    • (1996) Monatsh. Chem. , vol.127 , pp. 69
    • Falk, H.1    Chen, Q.-Q.2
  • 17
    • 85033132752 scopus 로고    scopus 로고
    • note
    • Hemiporphycene 8 affords stable complexes with numerous metals. Hemiporphycene-metal complexes with axial ligands have characteristic metal-centered chirality. Attempts to resolve the enantiomeric forms of the recently obtained complexes σ-phenyl-octaethylhemiporphycenatocobalt(III) and σ-methyl-octaethylhemiporphycenatorhodium (III) are in progress (collaboration between the groups of E. V. and J. L. S.).
  • 18
    • 4243973410 scopus 로고    scopus 로고
    • J. E. McMurry, Chem. Rev. 1989, 89, 1513; A. Fürstner, B. Bogdanović, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1989) Chem. Rev. , vol.89 , pp. 1513
    • McMurry, J.E.1
  • 19
    • 4243973410 scopus 로고    scopus 로고
    • J. E. McMurry, Chem. Rev. 1989, 89, 1513; A. Fürstner, B. Bogdanović, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1996) Angew. Chem. , vol.108 , pp. 2582
    • Fürstner, A.1    Bogdanović, B.2
  • 20
    • 0030444646 scopus 로고    scopus 로고
    • J. E. McMurry, Chem. Rev. 1989, 89, 1513; A. Fürstner, B. Bogdanović, Angew. Chem. 1996, 108, 2582; Angew. Chem. Int. Ed. Engl. 1996, 35, 2442.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2442
  • 22
    • 33748230214 scopus 로고
    • E. Vogel, P. Koch, X.-L. Hou, J. Lex, M. Lausmann, M. Kisters, M. A. Aukauloo, P. Richard, R. Guilard, Angew. Chem. 1993, 105, 1670; Angew. Chem. Int. Ed. Engl. 1993, 32, 1600.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1600
  • 23
    • 0642367311 scopus 로고
    • Ed.: D. Dolphin, Academic Press, New York
    • J. B. Paine III in The Porphyrins, Vol. I (Ed.: D. Dolphin), Academic Press, New York, 1978, p. 226.
    • (1978) The Porphyrins , vol.1 , pp. 226
    • Paine III, J.B.1
  • 24
    • 85033156021 scopus 로고    scopus 로고
    • note
    • 3CN, reflux, 3 h, inert atmosphere. (Equation Presented)
  • 27
    • 85033128588 scopus 로고    scopus 로고
    • note
    • 4 (room temperature, 1 h) and conventional workup.
  • 28
    • 85033127627 scopus 로고    scopus 로고
    • note
    • Additional support for the structure of 7 is provided by the similarity of its NMR spectrum to that of the dibenzyl ester 12, for which an X-ray crystal structure is available (as the rac diastereomer). (Equation Presented)
  • 29
    • 85033129323 scopus 로고    scopus 로고
    • note
    • An alternative route to 7 that avoids the tetrapyrrolic α,ω-dialdehyde 6 could involve an initial oxidative coupling of two molecules of 4 at the meso position with concomitant formation of a tetrapyrrylethane, followed by condensation with 5 to give 7. Among the evidence militating against this route is the observation that in the first step a labile product can be detected by thin layer chromatography that has a color comparable to that of 7, and from which 7 is formed only after treatment with ammonia.
  • 30
    • 85033143449 scopus 로고    scopus 로고
    • note
    • 1/2. Programs used: MolEN (Enraf-Nonius) for structure calculation and SHELXL-93 (G. M. Sheldrick, Universität Göttingen, Germany) for refinement. Calculated in the Regionales Rechenzentrum der Universität zu Köln. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 248. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
  • 31
    • 84990131664 scopus 로고    scopus 로고
    • Eds.: A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford
    • C. W. Bird, G. W. H. Cheeseman in Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984, p. 4; K. M. Smith, ibid., p. 386.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 4
    • Bird, C.W.1    Cheeseman, G.W.H.2
  • 32
    • 84990131664 scopus 로고    scopus 로고
    • C. W. Bird, G. W. H. Cheeseman in Comprehensive Heterocyclic Chemistry, Vol. 4 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, Oxford, 1984, p. 4; K. M. Smith, ibid., p. 386.
    • Comprehensive Heterocyclic Chemistry , pp. 386
    • Smith, K.M.1
  • 34
    • 85033154957 scopus 로고    scopus 로고
    • note
    • We thank Prof. Y.-D. Wu (Hongkong) for the calculations.
  • 35
    • 11944260641 scopus 로고
    • R. Bonnett, Chem. Soc. Rev. 1995, 24, 19; R. W. Boyle, D. Dolphin, Photochem. Photobiol. 1996, 64, 469.
    • (1995) Chem. Soc. Rev. , vol.24 , pp. 19
    • Bonnett, R.1
  • 37
    • 0642275488 scopus 로고
    • Eds.: E. G. Jung, M. Holick, de Gruyter, Berlin
    • g) formation is of decisive importance when considering 2,7,12,17-tetrapropylporphycene (16) and other porphycenes as possible "second-generation" PDT photosensitizers: K. Schaffner, E. Vogel, G. Jori in Biologic Effects of Light (Eds.: E. G. Jung, M. Holick), de Gruyter, Berlin, 1994, p. 312.
    • (1994) Biologic Effects of Light , pp. 312
    • Schaffner, K.1    Vogel, E.2    Jori, G.3
  • 41
    • 85033151994 scopus 로고    scopus 로고
    • note
    • Δ = (30±0.3) μs).
  • 45
    • 25344476752 scopus 로고
    • R. P. Burgner, A. M. Ponte Gonçalvez, Chem. Phys. Lett. 1977, 46, 275; B. M. Dzhagarov, G. P. Gurinovich, Nauka 1982, C. 59; O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1985, 82, 1779; B. M. Dzhagarov, G. P. Gurinovich, V. E. Novichenkov, K. I. Salokhiddinov, A. M. Shul'ga, V. A. Ganzha, Khim. Fiz. 1987, 6, 1069; K. Kikuchi, J. Kurabayashi, H. Kokubun, J. Kaizu, H. Kobayashi, J. Photochem. Photobiol. A: Chem. 1988, 45, 261.
    • (1977) Chem. Phys. Lett. , vol.46 , pp. 275
    • Burgner, R.P.1    Ponte Gonçalvez, A.M.2
  • 46
    • 0642336732 scopus 로고
    • R. P. Burgner, A. M. Ponte Gonçalvez, Chem. Phys. Lett. 1977, 46, 275; B. M. Dzhagarov, G. P. Gurinovich, Nauka 1982, C. 59; O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1985, 82, 1779; B. M. Dzhagarov, G. P. Gurinovich, V. E. Novichenkov, K. I. Salokhiddinov, A. M. Shul'ga, V. A. Ganzha, Khim. Fiz. 1987, 6, 1069; K. Kikuchi, J. Kurabayashi, H. Kokubun, J. Kaizu, H. Kobayashi, J. Photochem. Photobiol. A: Chem. 1988, 45, 261.
    • (1982) Nauka , vol.C , pp. 59
    • Dzhagarov, B.M.1    Gurinovich, G.P.2
  • 47
    • 36549104293 scopus 로고
    • R. P. Burgner, A. M. Ponte Gonçalvez, Chem. Phys. Lett. 1977, 46, 275; B. M. Dzhagarov, G. P. Gurinovich, Nauka 1982, C. 59; O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1985, 82, 1779; B. M. Dzhagarov, G. P. Gurinovich, V. E. Novichenkov, K. I. Salokhiddinov, A. M. Shul'ga, V. A. Ganzha, Khim. Fiz. 1987, 6, 1069; K. Kikuchi, J. Kurabayashi, H. Kokubun, J. Kaizu, H. Kobayashi, J. Photochem. Photobiol. A: Chem. 1988, 45, 261.
    • (1985) J. Chem. Phys. , vol.82 , pp. 1779
    • Ohno, O.1    Kaizu, Y.2    Kobayashi, H.3
  • 48
    • 0001708136 scopus 로고
    • R. P. Burgner, A. M. Ponte Gonçalvez, Chem. Phys. Lett. 1977, 46, 275; B. M. Dzhagarov, G. P. Gurinovich, Nauka 1982, C. 59; O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1985, 82, 1779; B. M. Dzhagarov, G. P. Gurinovich, V. E. Novichenkov, K. I. Salokhiddinov, A. M. Shul'ga, V. A. Ganzha, Khim. Fiz. 1987, 6, 1069; K. Kikuchi, J. Kurabayashi, H. Kokubun, J. Kaizu, H. Kobayashi, J. Photochem. Photobiol. A: Chem. 1988, 45, 261.
    • (1987) Khim. Fiz. , vol.6 , pp. 1069
    • Dzhagarov, B.M.1    Gurinovich, G.P.2    Novichenkov, V.E.3    Salokhiddinov, K.I.4    Shul'ga, A.M.5    Ganzha, V.A.6
  • 49
    • 0001206712 scopus 로고
    • R. P. Burgner, A. M. Ponte Gonçalvez, Chem. Phys. Lett. 1977, 46, 275; B. M. Dzhagarov, G. P. Gurinovich, Nauka 1982, C. 59; O. Ohno, Y. Kaizu, H. Kobayashi, J. Chem. Phys. 1985, 82, 1779; B. M. Dzhagarov, G. P. Gurinovich, V. E. Novichenkov, K. I. Salokhiddinov, A. M. Shul'ga, V. A. Ganzha, Khim. Fiz. 1987, 6, 1069; K. Kikuchi, J. Kurabayashi, H. Kokubun, J. Kaizu, H. Kobayashi, J. Photochem. Photobiol. A: Chem. 1988, 45, 261.
    • (1988) J. Photochem. Photobiol. A: Chem. , vol.45 , pp. 261
    • Kikuchi, K.1    Kurabayashi, J.2    Kokubun, H.3    Kaizu, J.4    Kobayashi, H.5


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