Article

Modification and Electrochemical Properties of Poly(phenylazomethine) Derivatives

Corresponding Author

Masayoshi Higuchi

[email protected]

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan. Fax: (+81) 29 860 4721Search for more papers by this author

Akari Hayashi,

Akari Hayashi

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan

Search for more papers by this author

Kimihisa Yamamoto,

Kimihisa Yamamoto

Department of Chemistry, Faculty of Science & Technology, Keio University, Yokohama 223-8522, Japan

Search for more papers by this author

Masayoshi Higuchi,

Corresponding Author

Masayoshi Higuchi

[email protected]

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan. Fax: (+81) 29 860 4721Search for more papers by this author

Akari Hayashi,

Akari Hayashi

Advanced Materials Laboratory, National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan

Search for more papers by this author

Kimihisa Yamamoto,

Kimihisa Yamamoto

Department of Chemistry, Faculty of Science & Technology, Keio University, Yokohama 223-8522, Japan

Search for more papers by this author

First published: 28 March 2006

https://doi.org/10.1002/masy.200650315

Citations: 1

About

PDF

Tools

Share a link

Email
Wechat
Bluesky

Abstract

Summary: Oligo(phenylazomethine)s (OPAs) and aniline-capped OPAs (OPA's) are used as model compounds of polyphenylazomethine (PPA), and their fundamental properties and their modification methods are investigated. Cyclic voltammograms of bis(diphenylmethyleneamino)benzene (OPA2′) showed irreversible redox response in the presence of trifluoroacetic acid. A selective synthesis of oligophenanthridine was achieved through the photocyclization of OPA2′ in concentrated sulfuric acid. Stepwise complexation behavior in dendritic poly(phenylazomethine)s (DPAs) was supported by the shell-selective reduction of the imines. Using the shell-selective reduction method and the terminal-modification method of the DPAs, the core and terminals of DPAs were functionalized by ferrocene units, respectively.

References

1 Z. F. Liu, H. C. Yan, K. B. Wang, T. Y. Kuang, J. P. Zhang, L. L. Gui, X. M. An, and W. R. Chang, Nature, 2004, 428, 287.
10.1038/nature02373
CAS PubMed Web of Science® Google Scholar
2 A. Ben-Shem, F. Frolow, and N. Nelson, Nature, 2003, 426, 630.
10.1038/nature02200
CAS PubMed Web of Science® Google Scholar
3 A. Zouni, H. T. Witt, J. Kern, P. Fromme, N. Krauss, W. Saenger, and P. Orth, Nature, 2001, 409, 739.
10.1038/35055589
CAS PubMed Web of Science® Google Scholar
4 P. Jordan, P. Fromme, H. T. Witt, O. Klukas, W. Saenger, and N. Krauss, Nature, 2001, 411, 909.
10.1038/35082000
CAS PubMed Web of Science® Google Scholar
5 P. A. delGiorgio, J. J. Cole, and A. Cimbleris, Nature, 1997, 385, 148.
10.1038/385148a0
CAS Web of Science® Google Scholar
6 G. T. Babcock and M. Wikstrom, Nature, 1992, 356, 301.
10.1038/356301a0
CAS PubMed Web of Science® Google Scholar
7 “ Macromolecular-metal Complexes”, eds. by F. Ciardelli, E. Tsuchida, D. Worle, Springer-Verlag, Berlin, 1995.
Google Scholar
8 “ Metal Containing Polymeric Materials”, ACS Symp. Ser. eds. by C. U. Pittman, B. M. Cullberston, J. E. Sheet, Plenum, New York, 1996.
Google Scholar
9 “ Macromolecular Complexes”, ed. by E. Tsuchida, VCH Publisher, New York, 1991.
Google Scholar
10 M. Higuchi, S. Shiki, and K. Yamamoto, Org. Lett., 2000, 2, 3079.
10.1021/ol006241t
CAS PubMed Web of Science® Google Scholar
11 M. Higuchi, S. Shiki, K. Ariga, and K. Yamamoto, J. Am. Chem. Soc., 2001, 123, 4414.
10.1021/ja004239r
CAS PubMed Web of Science® Google Scholar
12 K. Yamamoto, M. Higuchi, S. Shiki, M. Tsuruta, H. Chiba, Nature, 2002, 415, 509.
10.1038/415509a
CAS PubMed Web of Science® Google Scholar
13 M. Higuchi and K. Yamamoto, J. Syn. Org. Chem. Jpn, 2002, 60, 869.
10.5059/yukigoseikyokaishi.60.869
CAS Web of Science® Google Scholar
14 G. M. Badger, C. P. Joshua, G. E. Lewis, Tetrahedron Lett., 1964, 49, 3711.
10.1016/S0040-4039(01)89365-5
Google Scholar
15 M. Scholz, F. Dietz, M. Mühlstädt, Tetrahedron Lett., 1970, 32, 2835.
10.1016/S0040-4039(01)98353-4
Google Scholar
16 “ Supramolecular Polymers”, eds. by A. Ciferri, M. Dekker, New York, 2000.
10.1201/9780824746438
Google Scholar
17 “ Dendrimer I, II, III”, ed. by F. Vögtle, Springer, New York, 2001.
Google Scholar
18 “ Dendrimer and Dendrons”, eds. by G. R. Newkome, C. N. Moorefield, F. Vögtle, Wiley-VCH, New York, 2001.
10.1002/3527600612
Google Scholar
19 D. A. Tomalia, A. M. Naylor, and W. A. Goddard III, Angew. Chem. Int. Ed. Engl., 1990, 29, 138.
10.1002/anie.199001381
Web of Science® Google Scholar
20 S. M. Grayson and J. M. J. Fréchet, Chem. Rev., 2001, 101, 3819.
10.1021/cr990116h
CAS PubMed Web of Science® Google Scholar
21 C. Devadoss, P. Bharathi, and J. S. Moore, J. Am. Chem. Soc., 1996, 118, 9635.
10.1021/ja961418t
CAS Web of Science® Google Scholar
22 D. L. Jiang and T. Aida, Nature, 1997, 388, 454.
10.1038/41290
CAS Web of Science® Google Scholar
23 T. D. Selby and S. C. Blackstock, J. Am. Chem. Soc., 1998, 120, 12155.
10.1021/ja9821091
CAS Web of Science® Google Scholar
24 G. R. Newkome, E. He, and C. N. Moorefield, Chem. Rev., 1999, 99, 1689.
10.1021/cr9800659
CAS PubMed Web of Science® Google Scholar
25 D. Astruc and F. Chardac, Chem. Rev., 2001, 101, 2991.
10.1021/cr010323t
CAS PubMed Web of Science® Google Scholar
26 V. Balzani, P. Ceroni, A. Juris, M. Venturi, S. Campagna, F. Puntoriero, and S. Serroni, Coord. Chem. Rev., 2001, 219, 545.
10.1016/S0010-8545(01)00351-4
CAS Web of Science® Google Scholar

Citing Literature

Volume235, Issue1

Special Issue:Recent Advances and Novel Approaches in Macromolecule‐Metal Complexes

March 2006

Pages 121-126

Modification and Electrochemical Properties of Poly(phenylazomethine) Derivatives

Abstract

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Modification and Electrochemical Properties of Poly(phenylazomethine) Derivatives

Abstract

References

Citing Literature

References

Related

Information