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Volumn 61, Issue 14, 1996, Pages 4784-4792

Synthesis of novel heteroquaterphenoquinones and their electrochemical, structural, and spectroscopic characterization

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Indexed keywords


EID: 0000784863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600363     Document Type: Article
Times cited : (37)

References (54)
  • 3
    • 85011221785 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1986) J. Synth. Org. Chem. Jpn. , vol.44 , pp. 806
    • Takahashi, K.1
  • 4
    • 85011221785 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1993) Pure Appl. Chem. , pp. 127
    • Takahashi, K.1
  • 5
    • 85011221785 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1995) J. Chem. Soc., Chem. Commun. , vol.821
    • Takahashi, K.1    Tomitani, K.2
  • 6
    • 0029346212 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1995) Adv. Mater. , vol.7 , pp. 639
    • Takahashi, K.1    Tarutani, S.2
  • 7
    • 28444432953 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 620
    • Takahashi, K.1    Nihira, T.2    Akiyama, K.3    Ikegami, Y.4    Fukuyo, E.5
  • 8
    • 0000953876 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1994) Inorg. Chem. , vol.33 , pp. 1325
    • Ribou, A.-C.1    Launey, J.-P.2    Takahashi, K.3    Nihira, T.4    Tarutani, S.5    Spangler, C.W.6
  • 9
    • 85011221785 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 1539
    • Yui, K.1    Aso, Y.2    Otsubo, T.3    Ogura, F.4
  • 10
    • 37049079491 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 1118
    • Rao, V.P.1    Jen, A.K.-Y.2    Wong, K.Y.3    Drost, K.J.4
  • 11
    • 37049070709 scopus 로고
    • Takahashi, K. J. Synth. Org. Chem. Jpn. 1986, 44, 806. Takahashi, K. Pure Appl. Chem. 1993, 127. Takahashi, K.; Tomitani, K. J. Chem. Soc., Chem. Commun. 1995, 821. Takahashi, K.; Tarutani, S. Adv. Mater. 1995, 7, 639. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620. Ribou, A.-C.; Launey, J.-P.; Takahashi, K.; Nihira, T.; Tarutani, S.; Spangler, C. W. Inorg. Chem. 1994, 33, 1325. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. Rao, V. P.; Jen, A. K.-Y.; Wong, K. Y.; Drost, K. J. J. Chem. Soc., Chem. Commun. 1993, 1118. Kawai, S. H.; Gilat, S. L.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1994, 1011.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1011
    • Kawai, S.H.1    Gilat, S.L.2    Lehn, J.-M.3
  • 17
    • 84990115120 scopus 로고
    • Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 157. Yamashita, Y.; Tanaka , S.; Tomura, M. J. Chem. Soc., Chem. Commun. 1993, 652.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 1052
    • Yamashita, Y.1    Kobayashi, Y.2    Miyashi, T.3
  • 18
    • 37049067302 scopus 로고
    • Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 157. Yamashita, Y.; Tanaka , S.; Tomura, M. J. Chem. Soc., Chem. Commun. 1993, 652.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 157
    • Moore, A.J.1    Bryce, M.R.2
  • 19
    • 37049076174 scopus 로고
    • Yamashita, Y.; Kobayashi, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 1052. Moore, A. J.; Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 157. Yamashita, Y.; Tanaka , S.; Tomura, M. J. Chem. Soc., Chem. Commun. 1993, 652.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 652
    • Yamashita, Y.1    Tanaka, S.2    Tomura, M.3
  • 20
    • 0028915381 scopus 로고
    • Brackmann, T. W.; Tour, J. M. J. Am. Chem. Soc. 1995, 117, 4437. Effenberger, F.; Würthner, F.; Steybe, F. J. Org. Chem. 1995, 60, 2082.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4437
    • Brackmann, T.W.1    Tour, J.M.2
  • 24
    • 0003425622 scopus 로고
    • Academic Press, Inc.: London, Orlando, and references cited therein
    • Hains, A. H. In Method for the Oxidation of Organic Compounds; Academic Press, Inc.: London, Orlando, 1985; p 195 and references cited therein. Balogh, V.; Fetizon, M.; Golfier, M. J. Org. Chem. 1971, 36, 1339.
    • (1985) Method for the Oxidation of Organic Compounds , pp. 195
    • Hains, A.H.1
  • 25
    • 33947292856 scopus 로고
    • Hains, A. H. In Method for the Oxidation of Organic Compounds; Academic Press, Inc.: London, Orlando, 1985; p 195 and references cited therein. Balogh, V.; Fetizon, M.; Golfier, M. J. Org. Chem. 1971, 36, 1339.
    • (1971) J. Org. Chem. , vol.36 , pp. 1339
    • Balogh, V.1    Fetizon, M.2    Golfier, M.3
  • 26
    • 85033829482 scopus 로고    scopus 로고
    • note
    • Quinone 6 was not synthesized through the route described in Scheme 1.
  • 27
    • 85033820433 scopus 로고    scopus 로고
    • note
    • The EPR spectrum was too broad to obtain the splitting constants.
  • 28
  • 29
    • 0001364838 scopus 로고
    • Nakasuji, K.; Yoshida, K.; Murata, I. J. Am. Chem. Soc 1982, 104, 1432; 1983, 105, 5136. Takahashi, K.; Ogiyama, M. J. Chem. Soc., Chem. Commun. 1990, 1197.
    • (1983) J. Am. Chem. Soc , vol.105 , pp. 5136
  • 34
    • 85033818795 scopus 로고    scopus 로고
    • note
    • X-ray data for the crystallographic analysis of quinone 5 have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 37
    • 3342931284 scopus 로고
    • Garnier, F.; Tourillon, G.; Barraud, J. Y.; Dexpert, H. J. Mater. Sci. 1984, 161, 51. Cui, C. X.; Kertesz, M. Phys. Rev. B 1989, 40, 9661. Yang, R.; Dalsin, K. R.; Evans, D. F.; Christensen, L.; Hendrickson, W. A. J. Phys. Chem. 1989, 93, 511.
    • (1984) Mater. Sci. , vol.161 , pp. 51
    • Garnier, F.1    Tourillon, G.2    Barraud, J.Y.3    Dexpert, H.J.4
  • 38
    • 0000754840 scopus 로고
    • Garnier, F.; Tourillon, G.; Barraud, J. Y.; Dexpert, H. J. Mater. Sci. 1984, 161, 51. Cui, C. X.; Kertesz, M. Phys. Rev. B 1989, 40, 9661. Yang, R.; Dalsin, K. R.; Evans, D. F.; Christensen, L.; Hendrickson, W. A. J. Phys. Chem. 1989, 93, 511.
    • (1989) Phys. Rev. B , vol.40 , pp. 9661
    • Cui, C.X.1    Kertesz, M.2
  • 41
    • 0026141102 scopus 로고
    • Mo, Z.; Lee, K. B.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Macromolecules 1985, 18, 1972. Wragai, K.; Hotta, S. Synth. Met. 1991, 41, 519. Hotta, S.; Waragai, K. J. Mater. Chem. 1991, 1, 835.
    • (1991) Synth. Met. , vol.41 , pp. 519
    • Wragai, K.1    Hotta, S.2
  • 42
    • 37049088892 scopus 로고
    • Mo, Z.; Lee, K. B.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Macromolecules 1985, 18, 1972. Wragai, K.; Hotta, S. Synth. Met. 1991, 41, 519. Hotta, S.; Waragai, K. J. Mater. Chem. 1991, 1, 835.
    • (1991) J. Mater. Chem. , vol.1 , pp. 835
    • Hotta, S.1    Waragai, K.2
  • 43
    • 0024762536 scopus 로고
    • and references cited therein
    • Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1445 and references cited therein. Umehara, M.; Abe, M.; Oba, H. J. Synth. Org. Chem. Jpn. 1985, 43, 334. Fabian, J.; Zahradnik, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 677. Keil, D.; Hartmann, H. Liebigs Ann. Chem. 1995, 979.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 1445
    • Emmelius, M.1    Pawlowski, G.2    Vollmann, H.W.3
  • 44
    • 0022050905 scopus 로고
    • Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1445 and references cited therein. Umehara, M.; Abe, M.; Oba, H. J. Synth. Org. Chem. Jpn. 1985, 43, 334. Fabian, J.; Zahradnik, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 677. Keil, D.; Hartmann, H. Liebigs Ann. Chem. 1995, 979.
    • (1985) J. Synth. Org. Chem. Jpn. , vol.43 , pp. 334
    • Umehara, M.1    Abe, M.2    Oba, H.3
  • 45
    • 84990137022 scopus 로고
    • Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1445 and references cited therein. Umehara, M.; Abe, M.; Oba, H. J. Synth. Org. Chem. Jpn. 1985, 43, 334. Fabian, J.; Zahradnik, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 677. Keil, D.; Hartmann, H. Liebigs Ann. Chem. 1995, 979.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 677
    • Fabian, J.1    Zahradnik, R.2
  • 46
    • 84979200613 scopus 로고
    • Emmelius, M.; Pawlowski, G.; Vollmann, H. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 1445 and references cited therein. Umehara, M.; Abe, M.; Oba, H. J. Synth. Org. Chem. Jpn. 1985, 43, 334. Fabian, J.; Zahradnik, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 677. Keil, D.; Hartmann, H. Liebigs Ann. Chem. 1995, 979.
    • (1995) Liebigs Ann. Chem. , pp. 979
    • Keil, D.1    Hartmann, H.2
  • 47
    • 85033816532 scopus 로고    scopus 로고
    • note
    • The reflectivity was measured by A. Hirose at Mitsui Toatsu Chemicals, Inc., Yokohama, Japan, to whom the authors are indebted.
  • 48
    • 85033831510 scopus 로고    scopus 로고
    • note
    • Optical writing with a diode laser proved the clear pit forming character for a film of the dye 3. The details of these characteristics for optical storage media will be reported in other journals together with those for the quinones 4-6.
  • 49
    • 0346814452 scopus 로고
    • and references cited therein
    • Law, K. Y.Chem. Rev. 1993, 93, 449 and references cited therein. Yamaguchi, Y.; Tanaka, H.; Yokoyama, M. J. Chem. Soc., Chem. Commun 1990, 222. Carter, F. L. Molecular Electronic Devices; Marcel Dekker, New York, 1982. Alxandru, L.; Hopper, M. A. Mater. Microlichogr. 1984, 22, 435.
    • (1993) Chem. Rev. , vol.93 , pp. 449
    • Law, K.Y.1
  • 50
    • 37049071173 scopus 로고
    • Law, K. Y.Chem. Rev. 1993, 93, 449 and references cited therein. Yamaguchi, Y.; Tanaka, H.; Yokoyama, M. J. Chem. Soc., Chem. Commun 1990, 222. Carter, F. L. Molecular Electronic Devices; Marcel Dekker, New York, 1982. Alxandru, L.; Hopper, M. A. Mater. Microlichogr. 1984, 22, 435.
    • (1990) J. Chem. Soc., Chem. Commun , pp. 222
    • Yamaguchi, Y.1    Tanaka, H.2    Yokoyama, M.3
  • 51
    • 0004256338 scopus 로고
    • Marcel Dekker, New York
    • Law, K. Y.Chem. Rev. 1993, 93, 449 and references cited therein. Yamaguchi, Y.; Tanaka, H.; Yokoyama, M. J. Chem. Soc., Chem. Commun 1990, 222. Carter, F. L. Molecular Electronic Devices; Marcel Dekker, New York, 1982. Alxandru, L.; Hopper, M. A. Mater. Microlichogr. 1984, 22, 435.
    • (1982) Molecular Electronic Devices
    • Carter, F.L.1
  • 52
    • 3343012189 scopus 로고
    • Law, K. Y.Chem. Rev. 1993, 93, 449 and references cited therein. Yamaguchi, Y.; Tanaka, H.; Yokoyama, M. J. Chem. Soc., Chem. Commun 1990, 222. Carter, F. L. Molecular Electronic Devices; Marcel Dekker, New York, 1982. Alxandru, L.; Hopper, M. A. Mater. Microlichogr. 1984, 22, 435.
    • (1984) Mater. Microlichogr. , vol.22 , pp. 435
    • Alxandru, L.1    Hopper, M.A.2


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