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Synthesis of a New Class of Polyphenylated Phthalocyanines and Metallophthalocyanines

Published online by Cambridge University Press:  10 February 2011

Christopher J. Walsh  and
Braja K. Mandal
Christopher J. Walsh
Affiliation:
Department of Biological, Chemical, and Physical Sciences, Illinois Institute of Technology, Chicago, IL 60616
Braja K. Mandal
Affiliation:
Department of Biological, Chemical, and Physical Sciences, Illinois Institute of Technology, Chicago, IL 60616
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Abstract

We wish to report the synthesis of a new class of peripherally modified, polyphenylated phthalocyanines (Pcs) and metallophthalocyanines (MPcs). These compounds were synthesized by cyclic tetramerization of functionalized pentaphenylbenzophthalonitriles. The phthalonitriles were made in several steps via Diels-Alder cycloaddition between phenylethynylphthalonitrile and substituted tetracyclones. The polyphenylated design leads to enhanced solubility. Thin films can be cast from solutions of the butoxy and dodecaoxy substituted polyphenylated Pcs and MPcs. Cyclodehydrogenation of the Pcs was studied in an attempt to produce planar systems. Preliminary results indicate the pentaphenyl substituent is too bulky to planarize under the conditions employed.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 488: Symposium J – Electrical, Optical & Magnetic Properties of Organic IV , 1997 , 265
Copyright
Copyright © Materials Research Society 1998

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References

(1) For general references see: (a) Phthalocyanines Properties and Applications edited by Leznoff, C. C. and Lever, A. B. P. (VCH, New York, 1989). (b) Phthalocyanine Research and Applications edited by A. L. Thomas (CRC Press, New York, 1990).Google Scholar
(2) (a) Hanack, M., Lang, M., Adv. Materials 6(11), 819 (1994). (b) M. Hanack, S. Deger, A. Lange, Coord. Chem. Rev. 83, 115 (1988). (c) B. K. Mandal, A. K. Sinha, M. Kamath, Polymer Journal 27, 529 (1995).10.1002/adma.19940061103Google Scholar
(3) (a) Pol, J. F., Neelemen, E., Miltenburg, J. C., Zwikker, J. W., Nolte, R. J. M., Drenth, W., Macromolecules 23, 155 (1990). (b) M. J. Cook, D. A. Mayes, R. H. Poynter, J. Mater. Chem. 5, 2233 (1995).Google Scholar
(4) (a) Nonlinear Optics of Organic Molecules and Polymers edited by Nalwa, H. S., Miyata, S. (CRC Press, Boca Raton, FL, 1997). (b) J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, H. Sasabe, Science 273, 1533 (1996). (c) P. V. Bedworth, J. W. Perry, S. R. Marder, Chem. Comm. 1353, (1997). (d) J. S. Shirk, J. R. Lindle, F. J. Bartoli, M. E. J. Boyle, Phys. Chem. 96, 5847, (1992). (e) R. D. George, A. W. Snow, J. S. Shirk, S. R. Flom, R. G. S. Pong, Polym. Prep. 35(2), 236 (1994).Google Scholar
(5) Mandal, B. K., Bihari, B., Sinha, A. K., Kamath, M., Appl. Phys. Lett. 66(8), 932 (1995).Google Scholar
(6) (a) Kimura, M., Nakada, K., Yamaguchi, Y., Hanabusa, K., Shirai, H., Kobayashi, N., Chem. Comm. 1215 (1997). (b) B. K. Mandal, A. K. Sinha, X. Li, C. J. Walsh, D. Lamb, O. J. Smith, in Electrical, Optical and Magnetic Properties of Organic Solid State Materials III edited by A. KY. Jen, C. Y-C. Lee, L. R. Dalton, M. F. Rubner, G. E. Wnek, L. Y. Chiang (Mater. Res. Soc. 413, Pittsburgh, PA, 1996) pp. 431.Google Scholar
(7) see Perry, J. W., ref. 4a, pp. 813–839.Google Scholar
(8) (a) Kumar, U., Neenan, T. X., Macromolecules 28, 124 (1995). (b) Y. Sakaguchi, F. W. Harris, Polymer Journal 24(10), 1147 (1992). (d) for a general review see M. A. Ogliaruso, M.G. Romanelli, E. I. Becker, Chem. Rev. 65, 261 (1965).Google Scholar
(9) Griffiths, J., Roozpeikar, B., J. Chem. Soc. Perkin Trans. 1, 42 (1976).Google Scholar
(10) Alami, M., Ferri, F., Linsrumelle, G., Tetrahedron Lett. 34(40), 6403 (1993).Google Scholar
(11) Organic Experiments edited by Fieser, L. F. (D. C. Heath and Co., Boston, 1964) pp. 303.Google Scholar
(12) Mueller-Westerhoff, U. T., Zhou, M., J. Org. Chem. 59, 4988 (1994).10.1021/jo00096a049Google Scholar
(13) Snow, A. N., Jarvis, N. L., J. Amer. Chem. Soc. 106, 4706 (1984).Google Scholar
(14) Morgenroth, F., Reuther, E., Muellen, K., Angew. Chem. Int. Ed. Engl. 36, 632 (1997).Google Scholar