Synthesis and Properties of N-Arylcarbazolophane-Paracyclophane Combined with Carbazoles

Yosuke Nakamura; Takuzo Yamazaki; Yasuhiko Kakinoya; Hideyuki Shimizu; Jun Nishimura

doi:10.1055/s-2004-834859

SPECIALTOPIC

Synthesis and Properties of N-Arylcarbazolophane-Paracyclophane Combined with Carbazoles

Yosuke Nakamura, Takuzo Yamazaki, Yasuhiko Kakinoya, Hideyuki Shimizu, Jun Nishimura*
Department of Nano-Material Systems, Graduate School of Engineering, Gunma University, Kiryu, Gunma 376-8515, Japan
Fax: +81(277)301314; e-Mail: nisimura@chem.gunma-u.ac.jp;

Abstract

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Abstract

The intramolecular etherification of precursor tetrol 7 afforded N-arylcarbazolophane 5 as a single isomer. Carbazolophane 5 is considered to be a paracyclophane combined with a carbazole, and possesses excimer-like fluorescence properties with λ_max = 423 nm.

Key words

paracyclophane - carbazole - fluorescence - excimer

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References

1a Johnson GE. J. Chem. Phys. 1974, 61: 3002

1b Johnson GE. J. Chem. Phys. 1975, 63: 4047

1c De Schryver FC. Vandendriessche J. Toppet S. Demeyer K. Boens N. Macromolecules 1982, 15: 406

1d Masuhara H. Tamai N. Mataga N. De Schryver FC. Vandendriessche J. J. Am. Chem. Soc. 1983, 105: 7256

2a Johnson GE. J. Chem. Phys. 1975, 62: 4697

2b Sakai H. Itaya A. Masuhara H. Sasaki K. Kawata S. Polymer 1996, 37: 31

3a Tani K. Tohda Y. Hisada K. Yamamoto M. Chem. Lett. 1996, 145

3b For a recent contribution of this group on the synthesis of carbazolophanes, see: Tani K. Tohda Y. Takemura H. Ohkita H. Ito S. Yamamoto M. Chem. Commun. 2001, 1914

3c Ohkita H. Ito S. Yamamoto M. Tohda Y. Tani K. J. Phys. Chem. A 2002, 106: 2140

4a Nishimura J. Doi H. Ueda E. Ohbayashi A. Oku A. J. Am. Chem. Soc. 1987, 109: 5293

4b Nishimura J. Ohbayashi A. Doi H. Nishimura K. Oku A. Chem. Ber. 1988, 121: 2019

4c Nishimura J. Takeuchi M. Takahashi H. Ueda E. Matsuda Y. Oku A. Bull. Chem. Soc. Jpn. 1989, 62: 3161

4d Takeuchi M. Nishimura J. Tetrahedron Lett. 1992, 33: 5563

4e Nishimura J. Okada Y. Inokuma S. Nakamura Y. Gao SR. Synlett 1994, 884

4f Nishimura J. Nakamura Y. Hayashida Y. Kudo T. Acc. Chem. Res. 2000, 33: 679

5 Nakamura Y. Kaneko M. Yamanaka N. Tani K. Nishimura J. Tetrahedron Lett. 1999, 40: 4693

6 Nakamura Y. Kaneko M. Tani K. Shinmyozu T. Nishimura J. J. Org. Chem. 2002, 67: 8706

7a Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

7b Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2047

7c Hartwig JF. Synlett 1997, 329

8

The fluorescence excitation spectra were in good agreement with the corresponding absorption spectra in all cases.