Abstract
Dimeric phthalocyanines of a new type with a bridging 9,9,10,10-tetramethyl-9,10-dihydroanthracene fragment were synthesized. On the basis of X-ray diffraction analysis and molecular modeling of 9,9,10,10-tetramethyl-9,10-dihydroanthracene, a nearly planar structure was assumed for these phthalocyanines. The electronic absorption spectra of the obtained phthalocyanines and their monomeric and conjugated dimeric analogs were compared.
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P. D. Harvey, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, and R. Guilard, Academic Press, San Diego, California, 2003, 18, 63.
P. Erk and H. Hengelsberg, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, and R. Guilard, Academic Press, San Diego, California, 2003, 19, 105.
D. Wöhrle, O. Suvorova, R. Gerdes, O. Bartels, L. Lapok, N. Baziakina, S. Makarov, and A. Slodek, J. Porphyrins Phthalocyanines, 2004, 8, 1020.
J. H. Zagal, Coord. Chem. Rev., 1992, 119, 89.
R. Gerdes, O. Bartels, G. Schneider, D. Wöhrle, and G. Schulz-Ekloff, Polym. Adv. Technol., 2001, 12, 152.
K.-Y. Law, Chem. Rev., 1993, 93, 449.
E. Ben-Hur and W. Shun Chan, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, and R. Guilard, Academic Press, San Diego, California, 2003, 19, 1.
T. Inabe and H. Tajima, Chem. Rev., 2004, 104, 5503.
M. M. Nicholson, in Phthalocyanines: Properties and Applications, Eds C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1993, 3, 71.
C. Piechocki, J. Simon, A. Skoulios, D. Guillon, and P. Weber, J. Am. Chem. Soc., 1982, 104, 5245.
S. Flom, in The Porphyrin Handbook, Eds K. M. Kadish, K. M. Smith, and R. Guilard, Academic Press, San Diego, California, 2003, 19, 179.
N. Kobayashi, S. Nakajima, H. Ogata, and T. Fukuda, Chem. Eur. J., 2004, 10, 6294.
N. Kobayashi, Coord. Chem. Rev., 2002, 227, 129.
S. Makarov, Ch. Litwinski, E. A. Ermilov, O. Suvorova, B. Röder, and D. Wöhrle, Chem. Eur. J., 2006, 12, 1468.
E. S. Dodsworth, A. B. P. Lever, P. Seymour, and C. C. Leznoff, J. Phys. Chem., 1985, 89, 5698.
N. Kobayashi, H. Lam, W. A. Nevin, P. Janda, C. C. Leznoff, and A. B. P. Lever, Inorg. Chem., 1990, 29, 3415.
Y. Asano and N. Kobayashi, Tetrahedron Lett., 2004, 45, 9577.
W. J. Schutte, M. Sluyters-Rehbach, and J. H. Sluyters, J. Phys. Chem., 1993, 97, 6069.
K. Ishii, S. Abiko, M. Fujitsuka, O. Ito, and N. Kobayashi, J. Chem. Soc., Dalton Trans., 2002, 1735.
N. Kobayashi and A. B. P. Lever, J. Am. Chem. Soc., 1987, 109, 7433.
D. Wöhrle, L. Kreienhoop, and D. Schlettwein, in Phthalocyanines. Properties and Applications, Eds C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1996, 4, 219.
A. S. Davydov, Teoriya molekulyarnykh eksitonov [Theory of Molecular Excitons], Nauka, Moscow, 1968, 296 pp. (in Russian).
I. Granoth, Y. Segall, H. Leader, and R. Alkabets, J. Org. Chem., 1976, 41, 3682.
J. Tellenbröker and D. Kuck, Eur. J. Org. Chem., 2001, 1483.
N. F. Yannoni and J. Silverman, Science, 1964, 148, 231.
W. G. Ferrier and J. Iball, Chem. Ind., 1954, 1296.
G. M. Sheldrick, Empirical Absorption Correction Program, Universität Göttingen, Göttingen (Germany), 1996.
G. M. Sheldrick, Program for Crystal Structure Solution, Universität Göttingen, Göttingen (Germany), 1990.
G. M. Sheldrick, Program for Crystal Structure Refinement, Universität Göttingen, Göttingen (Germany), 1997.
HyperChem. R. 5.02 Pro, Hypercube Inc., Gainesville (USA), 1997.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1686–1692, October, 2006.
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Makarov, S.G., Maksimova, K.N., Baranov, E.V. et al. Synthesis and electronic spectra of dimeric phthalocyanines. Russ Chem Bull 55, 1748–1754 (2006). https://doi.org/10.1007/s11172-006-0483-9
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DOI: https://doi.org/10.1007/s11172-006-0483-9