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Reaction Principles and Crystal Structure Design for the Topochemical Polymerization of 1,3-Dienes

2002; Wiley; Volume: 41; Issue: 14 Linguagem: Inglês

10.1002/1521-3773(20020715)41

1521-3773

Akikazu Matsumoto, Kazuki Sada, Kohji Tashiro, Mikiji Miyata, Takashi Tsubouchi, Toshihiro Tanaka, Toru Odani, Sadamu Nagahama, Tomoyuki Tanaka, Katsunari Inoue, S. Saragai, S. Nakamoto,

Covalent Organic Framework Applications

Angewandte Chemie International EditionVolume 41, Issue 14 p. 2502-2505 Communication Reaction Principles and Crystal Structure Design for the Topochemical Polymerization of 1,3-Dienes Akikazu Matsumoto Dr., Akikazu Matsumoto Dr. [email protected] Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorKazuki Sada Dr., Kazuki Sada Dr. [email protected] 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 authorKohji Tashiro Prof. Dr., Kohji Tashiro Prof. Dr. [email protected] Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this authorMikiji Miyata Prof. Dr., Mikiji Miyata Prof. Dr. [email protected] 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 authorTakashi Tsubouchi, Takashi Tsubouchi Department of Applied Chemistry Graduate School of Engineering, Osaka City University Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan)Search for more papers by this authorToshihiro Tanaka Dr., Toshihiro Tanaka Dr. Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorToru Odani, Toru Odani Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorSadamu Nagahama, Sadamu Nagahama Department of Applied Chemistry Graduate School of Engineering, Osaka City University Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan)Search for more papers by this authorTomoyuki Tanaka, Tomoyuki Tanaka 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 authorKatsunari Inoue, Katsunari Inoue 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 authorSeishi Saragai Dr., Seishi Saragai Dr. Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this authorShinsuke Nakamoto, Shinsuke Nakamoto Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this author Akikazu Matsumoto Dr., Akikazu Matsumoto Dr. [email protected] Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorKazuki Sada Dr., Kazuki Sada Dr. [email protected] 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 authorKohji Tashiro Prof. Dr., Kohji Tashiro Prof. Dr. [email protected] Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this authorMikiji Miyata Prof. Dr., Mikiji Miyata Prof. Dr. [email protected] 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 authorTakashi Tsubouchi, Takashi Tsubouchi Department of Applied Chemistry Graduate School of Engineering, Osaka City University Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan)Search for more papers by this authorToshihiro Tanaka Dr., Toshihiro Tanaka Dr. Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorToru Odani, Toru Odani Department of Applied Chemistry Graduate School of Engineering, Osaka City University and PRESTO-JST Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan) Fax: (+81) 6-6605-2981Search for more papers by this authorSadamu Nagahama, Sadamu Nagahama Department of Applied Chemistry Graduate School of Engineering, Osaka City University Sugimoto, Sumiyoshi-ku, Osaka 558-8585 (Japan)Search for more papers by this authorTomoyuki Tanaka, Tomoyuki Tanaka 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 authorKatsunari Inoue, Katsunari Inoue 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 authorSeishi Saragai Dr., Seishi Saragai Dr. Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this authorShinsuke Nakamoto, Shinsuke Nakamoto Department of Macromolecular Science Graduate School of Science, Osaka University Toyonaka, Osaka 560-0043 (Japan)Search for more papers by this author First published: 15 July 2002 https://doi.org/10.1002/1521-3773(20020715)41:14 3.0.CO;2-9Citations: 98Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation 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 Stacking made to order: Weak intermolecular interactions such as 2D hydrogen-bonding networks, aromatic-ring stacking, and CH/π or halogen–halogen interactions account for the columnar organization of muconic and sorbic acid derivatives in the crystalline state (see picture). When the stacking distance is close to 5 Å these 1,3-dienes undergo topochemical polymerization upon irradiation. Supporting Information Supporting information for this article is available on the WWW under http://www.angewandte.org or from the author. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z18449_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1a G. M. J. Schmidt, Pure Appl. Chem. 1971, 27, 647; 1b G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989; 1c V. Enkelmann, G. Wegner, K. Novak, K. B. Wagener, J. Am. Chem. Soc. 1993, 115, 10 390; 1d A. Matsumoto, T. Odani, K. Sada, M. Miyata, K. Tashiro, Nature 2000, 405, 328; see also, M. D. Ward, Nature 2000, 405, 293; 1e K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025; 1f M. Alberecht, M. Lutz, A. L. Spek, G. van Koten, Nature 2000, 406, 970; see also, J. W. Steed, Nature 2000, 406, 943; 1g M. Irie, S. Kobatake, M. Horichi, Science 2001, 291, 1769; see also, J. R. Scheffer, C. Scott, Science 2001, 291, 1712; 1h G. R. Desiraju, Nature 2001, 412, 397; 1i B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629. 2 2a Y. Lu, Y. Yang, A. Sellinger, M. Lu, J. Huang, H. Fan, R. Haddad, G. Lopez, A. R. Burns, D. Y. Sasaki, J. Shelnutt, C. J. Brinker, Nature 2001, 410, 913; see also, G. D. Stucky, Nature 2001, 410, 885; 2b T. Aida, K. Tajima, Angew. Chem. 2001, 113, 3919; Angew. Chem. Int. Ed. 2001, 40, 3803; 2c K. Morigaki, T. Baumgart, A. Offenhausser, W. Knoll, Angew. Chem. 2001, 113, 1841; Angew. Chem. Int. Ed. 2001, 40, 172; 2d Y. Okawa, M. Aono, Nature 2001, 409, 683; 2e Y. Okawa, M. Aono, J. Chem. Phys. 2001, 115, 2317. 3 G. Wegner, Pure Appl. Chem. 1977, 49, 443. 4 V. Enkelmann, Adv. Polym. Sci. 1984, 63, 91. 5 M. Hasegawa, Adv. Phys. Org. Chem. 1995, 30, 117. 6 G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 3641. 7 J. Xiao, M. Yang, J. W. Lauher, F. W. Fowler, Angew. Chem. 2000, 112, 2216; Angew. Chem. Int. Ed. 2000, 39, 2132. 8 8a B. Tieke, J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 391; 8b B. Tieke, G. Chapuis, J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 2895; 8c B. Tieke, G. Chapuis, Crystallographically Ordered Polymers, Vol. 337 ( ), ACS Symposium Series, Washington DC, 1987, pp. 61; 8d B. Tieke, Colloid Polym. Sci. 1985, 263, 965; 8e B. Tieke, Adv. Polym. Sci. 1985, 71, 79; 8f B. Tieke, G. Chapuis, Mol. Cryst. Liq. Cryst. 1986, 137, 101. In this literature the crystal structures of the monomer and polymer are shown for derivatives of sorbic acid. The stacking distance between the monomers (ca. 4.9 Å), which is estimated from the crystal structure data in the literature, agrees well with our conclusion. 9 A. Matsumoto, T. Odani, Macromol. Rapid Commun. 2001, 22, 1195, and references therein. 10 K. Tashiro, A. N. Zadorin, S. Saragai, T. Kamae, A. Matsumoto, K. Yokoi, S. Aoki, Macromolecules 1999, 32, 7946. 11 A. Matsumoto, T. Odani, M. Chikada, K. Sada, M. Miyata, J. Am. Chem. Soc. 1999, 121, 11 122. 12 A. Matsumoto, S. Nagahama, T. Odani, J. Am. Chem. Soc. 2000, 122, 9109. 13 S. Nagahama, A. Matsumoto, J. Am. Chem. Soc. 2001, 123, 12 176. 14 We do not have sufficient crystal data for the E,Z monomers to discuss at the present because of the difficult isolation of pure isomers and single crystals. 15 In the previous papers θ1 and θ2 were defined in an alternative way. Formerly, direction I was parallel to a vector through the 2 and 3 carbon atoms (4 and 5 carbon atoms) for the Z,Z monomers and the 2 and 4 carbon atoms (3 and 5 carbon atoms) for the E,E monomers. However, it was not convenient for nonplanar molecules. Therefore, the values of θ1 and θ2 in this study are different from the previously reported values for some monomers. The present method is unambiguous and valid even for nonplanar 1,3-butadiene derivatives. 16 In Table 1 the data for the topochemically polymerizable monomers are shown. Supporting information is available for the nonpolymerizable monomers; see also, refs. [11], [17], [18], and [23]. 17 S. Saragai, K. Tashiro, S. Nakamoto, T. Kamae, A. Matsumoto, T. Tsubouchi, Polym. J. 2001, 33, 199. 18 S. Saragai, K. Tashiro, S. Nakamoto, A. Matsumoto, T. Tsubouchi, J. Phys. Chem. B 2001, 105, 4155. 19 19a G. R. Desiraju, Angew. Chem. 1995, 107, 2540; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311; 19b A. Nangia, G. R. Desiraju, Top. Curr. Chem. 1998, 198, 57. 20 20a G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999; 20b T. Steiner, Angew. Chem. 2002, 114, 50–80; Angew. Chem. Int. Ed. 2002, 41, 48–76; J. Am. Chem. Soc. 2002, 124, in press. 21 M. Nishio, M. Hirota, Y. Umezawa, The CH/π Interaction: Evidence, Nature, and Consequences, Wiley, New York, 1998. 22 S. M. Schlitter, H. P. Beck, Chem. Ber. 1996, 129, 1561. In this paper the authors speculated that the polymerization proceeds in the direction of the c-axis. However, the polymerization probably proceeds along the b-axis, and consequently, ds should be regarded as 5.04 Å. The small θ1 and θ2 values are disadvantageous for the polymerization, and they require rotational change in the conformation of the monomer molecules during polymerization. This would result in the collapse of the crystals, as reported in the paper. 23 A. Matsumoto, T. Tanaka, T. Tsubouchi, K. Tashiro, S. Saragai, S. Nakamoto, in preparation. 24 P. J. Jessup, C. B. Petty, J. Roos, L. E. Overman, Org. Synth. Coll. Vol. 1988, 6, 95. Citing Literature Volume41, Issue14July 15, 2002Pages 2502-2505 ReferencesRelatedInformation