Artigo Revisado por pares

Cis ‐Specific Topochemical Polymerization: Alternating Copolymerization of 7,7,8,8‐Tetrakis(methoxycarbonyl)quinodimethane with 7,7,8,8‐Tetracyanoquinodimethane in the Solid State

2011; Wiley; Volume: 123; Issue: 10 Linguagem: Inglês

10.1002/ange.201006928

ISSN

1521-3757

Autores

Takahito Itoh, Tatsuya Suzuki, Takahiro Uno, Masataka Kubo, Norimitsu Tohnai, Mikiji Miyata,

Tópico(s)

Luminescence and Fluorescent Materials

Resumo

Angewandte ChemieVolume 123, Issue 10 p. 2301-2304 Zuschrift Cis-Specific Topochemical Polymerization: Alternating Copolymerization of 7,7,8,8-Tetrakis(methoxycarbonyl)quinodimethane with 7,7,8,8-Tetracyanoquinodimethane in the Solid State† Prof. Dr. Takahito Itoh, Corresponding Author Prof. Dr. Takahito Itoh [email protected] Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorTatsuya Suzuki, Tatsuya Suzuki Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorDr. Takahiro Uno, Dr. Takahiro Uno Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorProf. Dr. Masataka Kubo, Prof. Dr. Masataka Kubo Graduate School of Regional Innovation Studies, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan)Search for more papers by this authorDr. Norimitsu Tohnai, Dr. Norimitsu Tohnai Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorProf. Dr. Mikiji Miyata, Prof. Dr. Mikiji Miyata Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)Search for more papers by this author Prof. Dr. Takahito Itoh, Corresponding Author Prof. Dr. Takahito Itoh [email protected] Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorTatsuya Suzuki, Tatsuya Suzuki Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorDr. Takahiro Uno, Dr. Takahiro Uno Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan), Fax: (+81) 59-231-9410Search for more papers by this authorProf. Dr. Masataka Kubo, Prof. Dr. Masataka Kubo Graduate School of Regional Innovation Studies, Mie University, 1577 Kurima Machiya-cho, Tsu-shi, Mie 514-8507 (Japan)Search for more papers by this authorDr. Norimitsu Tohnai, Dr. Norimitsu Tohnai Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorProf. Dr. Mikiji Miyata, Prof. Dr. Mikiji Miyata Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)Search for more papers by this author First published: 31 January 2011 https://doi.org/10.1002/ange.201006928Citations: 17 † This research was supported financially by a Grant-in-Aid for Scientific Research (No. 22550110) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Einkristall bleibt Einkristall: Ein kristalliner Charge-Transfer-Komplex aus den Titelverbindungen geht unter UV-Bestrahlung oder beim Erhitzen eine radikalische topochemische Polymerisation ein. Diese cis-spezifische Copolymerisation der substituierten Chinodimethane im Festkörper erfordert eine Verkippung der alternierenden Monomere im Cokristall (siehe Bild). References 1 1aG. Wegner, Z. Naturforsch. B 1969, 24, 824; 10.1515/znb-1969-0708 CASWeb of Science®Google Scholar 1bG. Wegner, Pure Appl. Chem. 1977, 49, 443; 10.1351/pac197749040443 CASWeb of Science®Google Scholar 1cV. Enkelmann, Adv. Polym. Sci. 1984, 63, 91; 10.1007/BFb0017652 CASWeb of Science®Google Scholar 1dT. Ogawa, Prog. Polym. Sci. 1995, 20, 943; 10.1016/0079-6700(95)00013-6 CASWeb of Science®Google Scholar 1eG. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290; 10.1002/ange.19971090330 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 248; 10.1002/anie.199702481 CASWeb of Science®Google Scholar 1fD. J. Sandman, I. B. Kim, J. M. Njus, D. C. Lee, A. L. Cholli, S. Sahoo, Macromol. Symp. 2003, 192, 99; 10.1002/masy.200390043 CASWeb of Science®Google Scholar 1gD. J. Sandman, J. M. Njus, B. Tran, Macromol. Symp. 2004, 217, 77; 10.1002/masy.200451209 CASWeb of Science®Google Scholar 1hY. H. Chan, J. T. Lin, I. W. P. Chen, C. H. Chen, J. Phys. Chem. B 2005, 109, 19161; 10.1021/jp0529366 CASPubMedWeb of Science®Google Scholar 1iS. Dei, A. Matsumoto, A. Matsumoto, Macromolecules 2008, 41, 2467. 10.1021/ma702789f CASWeb of Science®Google Scholar 2 2aM. Hasegawa, Chem. Rev. 1983, 83, 507; 10.1021/cr00057a001 CASWeb of Science®Google Scholar 2bM. Hasegawa, Adv. Phys. Org. Chem. 1995, 30, 117; 10.1016/S0065-3160(08)60034-9 CASGoogle Scholar 2cG. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 3641; 10.1021/ja974072a CASWeb of Science®Google Scholar 2dS. Takahashi, H. Miura, H. Kasai, S. Okada, H. Oikawa, H. Nakanishi, J. Am. Chem. Soc. 2002, 124, 10944; 10.1021/ja026564f CASPubMedWeb of Science®Google Scholar 2eD. Pestov, N. Levit, G. Tepper, Polymer 2003, 44, 3177; 10.1016/S0032-3861(03)00279-9 CASWeb of Science®Google Scholar 2fN. Levit, O. Guney-Altay, D. Pestov, G. Tepper, Macromolecules 2005, 38, 6528. 10.1021/ma050798c CASWeb of Science®Google Scholar 3 3aJ. Kiji, J. Kaiser, J. G. Wegner, R. C. Schulz, Polymer 1973, 14, 433; 10.1016/0032-3861(73)90009-8 CASWeb of Science®Google Scholar 3bV. Enkelmann, Chem. Mater. 1994, 6, 1337; 10.1021/cm00044a035 CASWeb of Science®Google Scholar 3cF. W. Fowler, J. W. Lauher, J. Phys. Org. Chem. 2000, 13, 850; 10.1002/1099-1395(200012)13:12 3.0.CO;2-L CASWeb of Science®Google Scholar 3dT. Hoang, J. W. Lauher, F. W. Fowler, J. Am. Chem. Soc. 2002, 124, 10656. 10.1021/ja027444a CASPubMedWeb of Science®Google Scholar 4 4aA. Matsumoto, T. Matsumura, S. Aoki, Macromolecules 1996, 29, 423; 10.1021/ma950996b CASWeb of Science®Google Scholar 4bA. Matsumoto, K. Yokoi, S. Aoki, K. Tashiro, T. Kamae, M. Kobayashi, Macromolecules 1998, 31, 2129; 10.1021/ma9717348 CASWeb of Science®Google Scholar 4cA. Matsumoto, K. Sada, K. Tashiro, M. Miyata, T. Tsubouchi, T. Tanaka, T. Odani, S. Nagahama, T. Tanaka, K. Inoue, S. Saragai, S. Nakamoto, Angew. Chem. 2002, 114, 2612; 10.1002/1521-3757(20020715)114:14 3.0.CO;2-3 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 2502; 10.1002/1521-3773(20020715)41:14 3.0.CO;2-9 CASPubMedWeb of Science®Google Scholar 4dA. Matsumoto, T. Tanaka, T. Tsubouchi, K. Tashiro, S. Saragai, S. Nakamoto, J. Am. Chem. Soc. 2002, 124, 8891; 10.1021/ja0205333 CASPubMedWeb of Science®Google Scholar 4eA. Matsumoto, Polym. J. 2003, 35, 93; 10.1295/polymj.35.93 CASWeb of Science®Google Scholar 4fS. Oshita, A. Matsumoto, Chem. Eur. J. 2006, 12, 2139; 10.1002/chem.200500771 CASPubMedWeb of Science®Google Scholar 4gD. Furukawa, A. Matsumoto, Macromolecules 2007, 40, 6048; 10.1021/ma070802f CASWeb of Science®Google Scholar 4hA. Matsumoto, D. Furukawa, Y. Mori, J. Tanaka, K. Oka, Cryst. Growth Des. 2007, 7, 1078; 10.1021/cg0606444 CASWeb of Science®Google Scholar 4iT. Ueno, D. Furukawa, A. Matsumoto, Macromol. Chem. Phys. 2008, 209, 357. 10.1002/macp.200700493 CASWeb of Science®Google Scholar 5 5aT. Itoh, S. Nomura, T. Uno, M. Kubo, K. Sada, M. Miyata, Angew. Chem. 2002, 114, 4482; 10.1002/1521-3757(20021115)114:22 3.0.CO;2-D Google ScholarAngew. Chem. Int. Ed. 2002, 41, 4306; 10.1002/1521-3773(20021115)41:22 3.0.CO;2-W CASPubMedWeb of Science®Google Scholar 5bS. Nomura, T. Itoh, H. Nakasho, T. Uno, M. Kubo, K. Sada, K. Inoue, M. Miyata, J. Am. Chem. Soc. 2004, 126, 2035; 10.1021/ja0386086 CASPubMedWeb of Science®Google Scholar 5cS. Nomura, T. Itoh, M. Ohtake, T. Uno, M. Kubo, A. Kajiwara, K. Sada, M. Miyata, Angew. Chem. 2003, 115, 5626; 10.1002/ange.200352355 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 5468; 10.1002/anie.200352355 CASPubMedWeb of Science®Google Scholar 5dT. Itoh, S. Nomura, M. Ohtake, T. Yoshida, T. Uno, M. Kubo, A. Kajiwara, K. Sada, M. Miyata, Macromolecules 2004, 37, 8230; 10.1021/ma035997f CASWeb of Science®Google Scholar 5eT. Itoh, S. Yamashita, S. Nomura, T. Uno, M. Kubo, N. Tohnai, M. Miyata, Macromolecules 2009, 42, 6473. 10.1021/ma901138k CASWeb of Science®Google Scholar 6 6aC. L. Schauer, E. Maturey, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1997, 119, 10245; 10.1021/ja9719539 CASWeb of Science®Google Scholar 6bA. Matsumoto, T. Odani, M. Chikada, K. Sada, M. Miyata, J. Am. Chem. Soc. 1999, 48, 11122; 10.1021/ja992558g CASWeb of Science®Google Scholar 6cJ. Xiao, M. Yang, J. W. Lauher, F. W. Fowler, Angew. Chem. 2000, 112, 2216; 10.1002/1521-3757(20000616)112:12 3.0.CO;2-H Google ScholarAngew. Chem. Int. Ed. 2000, 39, 2132; 10.1002/1521-3773(20000616)39:12 3.0.CO;2-8 CASPubMedWeb of Science®Google Scholar 6dA. Matsumoto, K. Katayama, T. Odani, K. Oka, K. Tashiro, S. Saragai, S. Nakamoto, Macromolecules 2000, 33, 7786; 10.1021/ma9917038 CASWeb of Science®Google Scholar 6eA. Matsumoto, S. Nagahama, T. Odani, J. Am. Chem. Soc. 2000, 122, 9109; 10.1021/ja001093n CASWeb of Science®Google Scholar 6fS. Nagahama, A. Matsumoto, J. Am. Chem. Soc. 2001, 123, 12176; 10.1021/ja011575e CASPubMedWeb of Science®Google Scholar 6gS. Nagahama, K. Inoue, K. Sada, M. Miyata, A. Matsumoto, Cryst. Growth Des. 2003, 3, 247; 10.1021/cg020070c CASWeb of Science®Google Scholar 6hR. Xu, V. Gramlich, H. Frauenrath, J. Am. Chem. Soc. 2006, 128, 5541; 10.1021/ja0603204 CASPubMedWeb of Science®Google Scholar 6iA. Sun, J. W. Lauher, N. S. Goroff, Science 2006, 312, 1030; 10.1126/science.1124621 CASPubMedWeb of Science®Google Scholar 6jL. Luo, C. Wilhelm, A. Sun, C. P. Grey, J. W. Lauher, N. S. Goroff, J. Am. Chem. Soc. 2008, 130, 7702; 10.1021/ja8011403 CASPubMedWeb of Science®Google Scholar 6kJ. W. Lauher, F. W. Fowler, N. S. Goroff, Acc. Chem. Res. 2008, 41, 1215; 10.1021/ar8001427 CASPubMedWeb of Science®Google Scholar 6lR. Xu, B. Schweizer, H. Frauenrath, Chem. Eur. J. 2009, 15, 9105. 10.1002/chem.200900985 CASPubMedWeb of Science®Google Scholar 7 7aS. Iwatsuki, T. Itoh, Macromolecules 1980, 13, 983; 10.1021/ma60076a043 CASWeb of Science®Google Scholar 7bS. Iwatsuki, T. Itoh, I. Yokotani, Macromolecules 1983, 16, 1817; 10.1021/ma00246a004 CASWeb of Science®Google Scholar 7cS. Iwatsuki, T. Itoh, K. Horiuchi, Macromolecules 1978, 11, 497; 10.1021/ma60063a014 CASWeb of Science®Google Scholar 7dS. Iwatsuki, T. Itoh, I. Yokotani, Macromolecules 1979, 12, 208; 10.1021/ma60068a008 CASWeb of Science®Google Scholar 7eS. Iwatsuki, T. Itoh, Macromolecules 1982, 15, 347; 10.1021/ma00230a029 CASWeb of Science®Google Scholar 7fS. Iwatsuki, T. Itoh, Macromolecules 1983, 16, 1571; 10.1021/ma00244a004 CASWeb of Science®Google Scholar 7gT. Itoh, H. K. Hall, Jr., Macromolecules 1990, 23, 2836; 10.1021/ma00213a003 CASWeb of Science®Google Scholar 7hT. Itoh, Prog. Polym. Sci. 2001, 26, 1019. 10.1016/S0079-6700(01)00012-0 CASWeb of Science®Google Scholar 8X-ray diffraction data were collected on a Rigaku R-AXIS RAPID diffractometer with a 2D area detector by using graphite-monochromatized CuKα radiation (λ=1.54187 Å). Direct methods (SIR-2004) were used for the solution of the structure.[10] All calculations were performed with the observed reflections [I>2σ(I)] with the program CrysalStructure crystallographic software package[11] except for refinement, which was performed with SHELXL-97.[12] All non-hydrogen atoms were refined with anisotropic displacement parameters, and hydrogen atoms were placed in idealized positions and refined as rigid atoms with the relative isotropic displacement parameters. Crystal-structure data for the 1⋅2 cocrystal: platelet, C14H10N2O4, Mr=270.24, 0.10×0.10×0.10 mm3, triclinic, space group (No. 2), a=7.7988(3), b=8.1224(3), c=11.8862(4) Å, α=76.603(3), β=79.720(3), γ=61.862(3)°, V=643.78(4) Å3, Z=2, ρcalcd=1.394 g cm−3, T=123.1 K, μ(CuKα)=0.880 mm−1, 2θmax=136°, 6875 reflections collected, 1849 unique (Rint=0.067) reflections. The final R1 and wR2 values were 0.0485 [I>2.0σ(I)] and 0.1420 (all data), respectively. Crystal structure data for poly(1⋅2): platelet, C14H10N2O4, Mr=270.24, 0.10×0.10×0.10 mm3, triclinic, space group (No. 2), a=7.0153(9), b=7.8433(9), c=12.1307(14) Å, α=80.101(5), β=86.502(6), γ=70.580(6)°, V=620.11(13) Å3, Z=2, ρcalcd=1.447 g cm−3, T=123.1 K, μ(CuKα)=0.914 mm−1, 2θmax=136°, 11 245 reflections collected, 3054 unique (Rint=0.279) reflections. The final R1 and wR2 values were 0.1377 [I>2.0σ(I)] and 0.4058 (all data), respectively. Google Scholar 9A. A. Bright, A. F. Garito, A. Heeger, Solid State Commun. 1973, 13, 943. 10.1016/0038-1098(73)90405-5 CASWeb of Science®Google Scholar 10M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381. 10.1107/S002188980403225X CASWeb of Science®Google Scholar 11CrystalStructure 3.8, Crystal Structure Analysis Package, Rigaku and Rigaku Americas (2000–2007): The Woodlands. Google Scholar 12G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen (Germany), 1997. Google Scholar Citing Literature Volume123, Issue10March 1, 2011Pages 2301-2304 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation

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