Oligophenylenevinylene phane dimers: Probing the effect of contact site on the optical properties of bichromophoric pairs

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1289-1297

  Wang, Shujun ^a   Bazan, Guillermo C ^a   Tretiak, Sergei ^b   Mukamel, Shaul ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PARACYCLOPHANE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; OPTICAL ROTATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033998173     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991611y     Document Type: Article

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32. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
33. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
34. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
35. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
36. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
37. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
38. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
39. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
40. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. Chem. Phys. 1978, 29, 181. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitami, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976, 36, 3121. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187. (d) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858. For studies of cycloaddition reactions see: (e) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas- Laurent, J. J. Chem. Soc., Chem. Commun. 1994, 1075. (f) Okada, Y.; Ishii, F.; Akiyama, I.; Nishimura, J. Chem. Lett. 1992, 1579. (g) Ferguson, J. Chem. Rev. 1986, 86, 957. (h) Grieiving, H.; Hopf, H.; Jones, P. G.; Bubenitscheck, P.; Desvergne, J. P.; Bouas-Laurent, Liebigs. Ann. 1995, 1949. (i) Marquis, D.; Desvergne, J. P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
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