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Volumn 126, Issue 51, 2004, Pages 16793-16803

Synthesis and properties of highly fluorescent indolizino[3,4,5-ab] isoindoles

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; ELECTROCHEMISTRY; FLUORESCENCE; LUMINESCENCE; OPTICAL DEVICES; OPTICAL PROPERTIES; OXIDATION; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 11244344107     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049214x     Document Type: Article
Times cited : (118)

References (98)
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    • Tominaga, Y.1    Shiroshita, Y.2    Gotou, H.3    Matsuda, Y.4
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
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    • Tominaga, Y.1    Shigematsu, Y.2    Saeki, K.3
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
    • (1990) Heterocycles , vol.31 , pp. 1785
    • Yamauchi, J.1    Uchida, T.2    Matsumoto, K.3
  • 36
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
    • (1985) Heterocycles , vol.23 , pp. 2773
    • Matsumoto, K.1    Yamauchi, J.2    Uchida, T.3
  • 37
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
    • (1988) J. Heterocycl. Chem. , vol.25 , pp. 1793
    • Uchida, T.1    Aoyama, K.2    Nishikawa, M.3    Kuroda, T.4    Okamoto, T.5
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
    • (1982) Chem. Lett. , pp. 869
    • Matsumoto, K.1    Uchida, T.2    Sugi, T.3    Yagi, Y.4
  • 39
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    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , vol.21 , pp. 2599
    • Matsumoto, K.1    Katsura, H.2    Uchida, T.3    Aoyama, K.4    Machiguchi, T.5
  • 40
    • 0001657533 scopus 로고    scopus 로고
    • f-k) have been previously reported. (a) Kajigaesh, S.; Mori, S.; Fujisaki, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1985, 58, 3547. (b) Matsumoto, K.; Uchida, T.; Kato, T.; Toda, M.; Aoyama, K.; Konishi, H. Heterocycles 1990, 31, 593. (c) Tominaga, Y.; Shiroshita, Y.; Gotou, H.; Matsuda, Y. Heterocycles 1986, 24, 3071. (d) Castle, L. W.; Tominaga, Y.; Castle, R. N. J. Heterocycl Chem. 1995, 32, 1033. (e) Tominaga, Y.; Shigematsu, Y.; Saeki, K. J. Heterocycl. Chem. 2002, 39, 571. (f) Yamauchi, J.; Uchida, T.; Matsumoto, K. Heterocycles 1990, 31, 1785. (g) Matsumoto, K.; Yamauchi, J. Uchida, T. Heterocycles 1985, 23, 2773. (h) Uchida, T.; Aoyama, K.; Nishikawa, M.; Kuroda, T.; Okamoto, T. J. Heterocycl. Chem. 1988, 25, 1793. (i) Matsumoto, K.; Uchida, T.; Sugi, T.; Yagi, Y. Chem. Lett. 1982, 869. (j) Matsumoto, K.; Katsura, H.; Uchida, T.; Aoyama, K.; Machiguchi, T. J. Chem. Soc., Perkin Trans. 1 1996, 21, 2599. (k) Matsumoto, K.; Katsura, H.; Yamauchi, J.; Uchida, T.; Aoyama, K.; Machiguchi, T. Bull. Soc. Chim. Fr. 1996, 133, 891.
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    • Matsumoto, K.1    Katsura, H.2    Yamauchi, J.3    Uchida, T.4    Aoyama, K.5    Machiguchi, T.6
  • 47
    • 11244271130 scopus 로고    scopus 로고
    • note
    • max of the fluorescence spectra, and the Stokes shift are given in the Supporting Information.
  • 49
    • 11244330170 scopus 로고    scopus 로고
    • note
    • 17 and the Stokes shift was calculated between the strongest emission and absorption bands. Thus, it is difficult to compare the Stokes shift in compound 2 with those of compounds 3-5.
  • 50
    • 11244320165 scopus 로고    scopus 로고
    • note
    • 1H NMR before and after addition of acetic acid.
  • 64
    • 11244271128 scopus 로고    scopus 로고
    • note
    • Additionally, compounds 2 and 13 also have high luminescence in a solid state, which indicates those have little self-quenching in condensed states.
  • 71
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    • The reorganization energy (λ) for self-exchange corresponds to the sum of the geometry relaxation energies upon going from the neutral-state geometry to the charged-state geometry and vice versa. These two portions of λ are typically nearly identical, see: Malagoli, M.; Brédas. J.-L. Chem. Phys. Lett. 2000, 327, 13.
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    • Malagoli, M.1    Brédas, J.-L.2
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    • note
    • 2): δ 143.2, 133.3, 132.1, 124.7, 124.4, 124.3, 120.4, 118.2, 44.8.
  • 78
    • 0004300084 scopus 로고    scopus 로고
    • Mallard, W. G., Linstrom, P. J., Eds.; NIST Chemistry WebBook, NIST Standard Reference Database No. 69, July 2001; National Institute of Standards and Technology: Gaithersburg, MD
    • Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. In Ion Energetics Data; Mallard, W. G., Linstrom, P. J., Eds.; NIST Chemistry WebBook, NIST Standard Reference Database No. 69, July 2001; National Institute of Standards and Technology: Gaithersburg, MD, 2001 (http://webbook.nist.gov).
    • (2001) Ion Energetics Data
    • Lias, S.G.1    Bartmess, J.E.2    Liebman, J.F.3    Holmes, J.L.4    Levin, R.D.5    Mallard, W.G.6
  • 80
    • 11244330914 scopus 로고    scopus 로고
    • note
    • The pairs of (1,3-H), (6, 9-H), and (7,8-H) in protonated compound 5 are changeable.
  • 90
    • 11244271129 scopus 로고    scopus 로고
    • note
    • This glass transition temperature is considerably high, which means this compound could have high thermal stability in a device. The ball-shape structure could be a good methodology for high Tg compounds.


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