モリブデン錯体触媒を用いる非環式ジエンメタセシス重合とWittig型カップリング反応による末端官能基化π共役ポリマーのone-pot精密合成
Mo(CHCMe2Ph)(N-2,6-Me2C6H3)[OCMe(CF3)2)]2触媒による2,7-divinyl-9,9-di-n-octyl-fluoreneの非環式ジエンメタセシス（ADMET）重合後，反応系内にモリブデン触媒を追加添加し，さらに所定のアルデヒドとのWittig型反応にて，高収率で両末端官能基化した共役ポリマー，poly(9,9-di-n-octyl-fluorene vinylene)s (EF-PFVs)，を合成した。重合時に残存したポリマーの末端ビニル基と追加添加したモリブデン触媒とのオレフィンメタセシス反応により，ポリマー末端をすべてアルキリデン（カルベン）種と変...
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| Published in | Journal of the Japan Petroleum Institute Vol. 59; no. 5; pp. 197 - 203 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
公益社団法人 石油学会
01.09.2016
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| Online Access | Get full text |
| ISSN | 1346-8804 1349-273X |
| DOI | 10.1627/jpi.59.197 |
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| Abstract | Mo(CHCMe2Ph)(N-2,6-Me2C6H3)[OCMe(CF3)2)]2触媒による2,7-divinyl-9,9-di-n-octyl-fluoreneの非環式ジエンメタセシス（ADMET）重合後，反応系内にモリブデン触媒を追加添加し，さらに所定のアルデヒドとのWittig型反応にて，高収率で両末端官能基化した共役ポリマー，poly(9,9-di-n-octyl-fluorene vinylene)s (EF-PFVs)，を合成した。重合時に残存したポリマーの末端ビニル基と追加添加したモリブデン触媒とのオレフィンメタセシス反応により，ポリマー末端をすべてアルキリデン（カルベン）種と変換することで， 続くWittig型のカップリング反応による末端官能基化が定量的な収率で進行した。本手法により，欠陥や不純物の混入のない，高立体規則性（all trans）の各種末端官能基化共役ポリマーがone-potで精密合成可能となった。 |
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| AbstractList | Mo(CHCMe2Ph)(N-2,6-Me2C6H3)[OCMe(CF3)2)]2触媒による2,7-divinyl-9,9-di-n-octyl-fluoreneの非環式ジエンメタセシス（ADMET）重合後，反応系内にモリブデン触媒を追加添加し，さらに所定のアルデヒドとのWittig型反応にて，高収率で両末端官能基化した共役ポリマー，poly(9,9-di-n-octyl-fluorene vinylene)s (EF-PFVs)，を合成した。重合時に残存したポリマーの末端ビニル基と追加添加したモリブデン触媒とのオレフィンメタセシス反応により，ポリマー末端をすべてアルキリデン（カルベン）種と変換することで， 続くWittig型のカップリング反応による末端官能基化が定量的な収率で進行した。本手法により，欠陥や不純物の混入のない，高立体規則性（all trans）の各種末端官能基化共役ポリマーがone-potで精密合成可能となった。 |
| Author | 稲垣, 昭子 宮下, 智成 野村, 琴広 |
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| Copyright | 2016 公益社団法人石油学会 |
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C., Müllen, K., “Macromolecular Engineering,” eds. by Matyjaszewski, K., Gnanou, Y., Leibler, L., Wiley-VCH, Weinheim (2007), Part 4, Chap. 6, pp. 2225-2262. 9) Ego, C., Marsitzky, D., Becker, S., Zhang, J., Grimsdale, A. C., Müllen, K., MacKenzie, J. D., Silva, C., Friend, R. H., J. Am. Chem. Soc., 125, 437 (2003). 30) Miyashita, T., Nomura, K., Macromolecules, 49, 518 (2016). 34) Anuragudom, P., Newaz, S. S., Phanichphant, S., Lee, T. R., Macromolecules, 39, 3494 (2006). 32) Oskam, H. J., Fox, H. H., Yap, B. K., McConville, H. D., O’Dell, R., Lichtenstein, J. B., Schrock, R. R., J. Organomet. Chem., 459, 185 (1993). 16) Nomura, K., Miyamoto, Y., Morimoto, H., Geerts, Y., J. Polym. Sci., Part A, Polym. Chem., 43, 6166 (2005). 14) Nomura, K., Morimoto, H., Imanishi, Y., Ramhani, Z., Geerts, Y., J. Polym. Sci., Part A, Polym. Chem., 39, 2463 (2001). 13) El-Khouly, M. E., Chen, Y., Zhuang, X., Fukuzumi, S., J. Am. Chem. Soc., 131, 6370 (2009). 19) Berda, E. B., Wagener, K. B., “Polymer Science, A Comprehensive Reference,” eds. by Matyjaszewski, K., Müllen, M., Elsevier, BV, Amsterdam (2012), Vol. 5, pp. 195-216. 24) Abdellatif, M. M., Nomura, K., ACS Macro Lett., 1, 423 (2012). 5) Li, C., Liu, M., Pschirer, N. G., Baumgarten, M., Müllen, K., Chem. Rev., 110, 6817 (2010). 33) As reported previously, 14-16 the calibration with polystyrene standards often overestimates the molecular weight averages of rigid conjugated polymers. Therefore, GPC curves versus structurally similar soluble PPP [poly(p-phenylene)] standards were recorded,14 and the Mn values of rodlike polymers measured versus polymer standards are overestimated by a factor of 1.6. For a related article on measuring Mn and Mw/Mn values by PPP standards, Marsitzky, D., Brand, T., Geerts, Y., Klapper, M., Müllen, K., Macromol. Rapid Commun., 19, 385 (1998). 21) Atallah, P., Wagener, K. B., Schulz, M. D., Macromolecules, 46, 4735 (2013). 23) Kuwabara, S., Yamamoto, N., Sharma, P. M. V., Takamizu, K., Fujiki, M., Geerts, Y., Nomura, K., Macromolecules, 44, 3705 (2011). 4) Grimsdale, A. C., Chan, K. L., Martin, R. E., Jokisz, P. G., Holmes, A. B., Chem. Rev., 109, 897 (2009). 6) Zade, S. S., Zamoshchik, N., Bendikov, M., Acc. Chem. Res., 44, 14 (2011). 26) Nomura, K., Haque, T., Onuma, T., Hajjaj, F., Asano, M. S., Inagaki, A., Macromolecules, 46, 9563 (2013). 38) Li, T., David Curtis, M., Francis, A. H., Macromolecules, 35, 4628 (2002). 3) Laclerc, N., Heiser, T., Brochon, C., Hadziioannou, G., “Macromolecular Engineering,” eds. by Matyjaszewski, K., Gnanou, Y., Leibler, L., Wiley-VCH, Weinheim (2007) , Part 4, Chap. 10, pp. 2369-2408. 17) Lehman Jr., S. E., Wagener, K. B., “Handbook of Metathesis: Catalyst Development,” ed. by Grubbs, R. H., Wiley-VCH, Weinheim (2003), Part 3, Chap. 3.9, pp. 283-353. 8) Miteva, T., Meisel, A., Knoll, W., Nothofer, H. G., Scherf, U., Müller, D. C., Meerholz, K., Yasuda, A., Neher, D., Adv. Mater., 13, 565 (2001). 36) Zhu, Y., Wolf, M. O., J. Am. Chem. Soc., 122, 10121 (2000). 15) Nomura, K., Yamamoto, N., Ito, R., Fujiki, M., Geerts, Y., Macromolecules, 41, 4245 (2008). 29) Perspectives (related reviewing article including end-functionalization of ROMP polymer by adopting the similar approach, olefin metathesis with Wittig-type coupling), Nomura, K., Abdellatif, M. M., Polymer, 51, 1861 (2010). |
| References_xml | – reference: 21) Atallah, P., Wagener, K. B., Schulz, M. D., Macromolecules, 46, 4735 (2013). – reference: 27) Nomura, K., Haque, T., Miwata, T., Inagaki, A., Takamizu, K., Polym. Chem., 6, 380 (2015). – reference: 7) Park, J. K., Jo, J., Seo, J. H., Moon, J. S., Park, Y. D., Lee, K., Heeger, A. J., Bazan, G. C., Adv. Mater., 23, 2430 (2011). – reference: 20) Berda, E. B., Wagener, K. B., “Synthesis of Polymers, New Structures and Methods,” eds. by Schluter, D., Hawker, C., Sakamosto, J., Wiley-VCH, Weinhein, Germany (2012), p. 587. – reference: 17) Lehman Jr., S. E., Wagener, K. B., “Handbook of Metathesis: Catalyst Development,” ed. by Grubbs, R. H., Wiley-VCH, Weinheim (2003), Part 3, Chap. 3.9, pp. 283-353. – reference: 14) Nomura, K., Morimoto, H., Imanishi, Y., Ramhani, Z., Geerts, Y., J. Polym. Sci., Part A, Polym. Chem., 39, 2463 (2001). – reference: 1) Grimsdale, A. C., Müllen, K., “Macromolecular Engineering,” eds. by Matyjaszewski, K., Gnanou, Y., Leibler, L., Wiley-VCH, Weinheim (2007), Part 4, Chap. 6, pp. 2225-2262. – reference: 12) Asaoka, S., Takeda, N., Iyoda, T., Cook, A. R., Miller, J. R., J. Am. Chem. Soc., 130, 11912 (2008). – reference: 30) Miyashita, T., Nomura, K., Macromolecules, 49, 518 (2016). – reference: 34) Anuragudom, P., Newaz, S. S., Phanichphant, S., Lee, T. R., Macromolecules, 39, 3494 (2006). – reference: 29) Perspectives (related reviewing article including end-functionalization of ROMP polymer by adopting the similar approach, olefin metathesis with Wittig-type coupling), Nomura, K., Abdellatif, M. M., Polymer, 51, 1861 (2010). – reference: 31) Miyashita, T., Inagaki, A., Nomura, K., The results were partly introduced at 45th Petroleum-Petrochemicals Symposium of Japan Petroleum Institute, November, Nagoya, Japan (2015), 1F15. – reference: 33) As reported previously, 14-16 the calibration with polystyrene standards often overestimates the molecular weight averages of rigid conjugated polymers. Therefore, GPC curves versus structurally similar soluble PPP [poly(p-phenylene)] standards were recorded,14 and the Mn values of rodlike polymers measured versus polymer standards are overestimated by a factor of 1.6. For a related article on measuring Mn and Mw/Mn values by PPP standards, Marsitzky, D., Brand, T., Geerts, Y., Klapper, M., Müllen, K., Macromol. Rapid Commun., 19, 385 (1998). – reference: 28) Haque, T., Nomura, K., Catalysts, 5, 500 (2015). – reference: 36) Zhu, Y., Wolf, M. O., J. Am. Chem. Soc., 122, 10121 (2000). – reference: 26) Nomura, K., Haque, T., Onuma, T., Hajjaj, F., Asano, M. S., Inagaki, A., Macromolecules, 46, 9563 (2013). – reference: 16) Nomura, K., Miyamoto, Y., Morimoto, H., Geerts, Y., J. Polym. Sci., Part A, Polym. Chem., 43, 6166 (2005). – reference: 32) Oskam, H. J., Fox, H. H., Yap, B. K., McConville, H. D., O’Dell, R., Lichtenstein, J. B., Schrock, R. R., J. Organomet. Chem., 459, 185 (1993). – reference: 23) Kuwabara, S., Yamamoto, N., Sharma, P. M. V., Takamizu, K., Fujiki, M., Geerts, Y., Nomura, K., Macromolecules, 44, 3705 (2011). – reference: 4) Grimsdale, A. C., Chan, K. L., Martin, R. E., Jokisz, P. G., Holmes, A. B., Chem. Rev., 109, 897 (2009). – reference: 24) Abdellatif, M. M., Nomura, K., ACS Macro Lett., 1, 423 (2012). – reference: 25) Takamizu, K., Inagaki, A., Nomura, K., ACS Macro Lett., 2, 980 (2013). – reference: 3) Laclerc, N., Heiser, T., Brochon, C., Hadziioannou, G., “Macromolecular Engineering,” eds. by Matyjaszewski, K., Gnanou, Y., Leibler, L., Wiley-VCH, Weinheim (2007) , Part 4, Chap. 10, pp. 2369-2408. – reference: 19) Berda, E. B., Wagener, K. B., “Polymer Science, A Comprehensive Reference,” eds. by Matyjaszewski, K., Müllen, M., Elsevier, BV, Amsterdam (2012), Vol. 5, pp. 195-216. – reference: 35) Liu, Q., Liu, W., Yao, B., Tian, H., Xie, Z., Geng, Y., Wang, F., Macromolecules, 40, 1851 (2007). – reference: 9) Ego, C., Marsitzky, D., Becker, S., Zhang, J., Grimsdale, A. C., Müllen, K., MacKenzie, J. D., Silva, C., Friend, R. H., J. Am. Chem. Soc., 125, 437 (2003). – reference: 11) Beljonne, D., Pourtois, G., Silva, C., Hennebicq, E., Herz, L. M., Friend, R. H., Scholes, G. D., Setayesh, S., Müllen, K., Brédas, J. L., Proc. Natl. Acad. Sci. U. S. A., 99, 10982 (2002). – reference: 13) El-Khouly, M. E., Chen, Y., Zhuang, X., Fukuzumi, S., J. Am. Chem. Soc., 131, 6370 (2009). – reference: 38) Li, T., David Curtis, M., Francis, A. H., Macromolecules, 35, 4628 (2002). – reference: 6) Zade, S. S., Zamoshchik, N., Bendikov, M., Acc. Chem. Res., 44, 14 (2011). – reference: 10) Gong, X., Ma, W., Ostrowski, J. C., Bechgaard, K., Bazan, G. C., Heeger, A. J., Xiao, S., Moses, D., Adv. Funct. Mater., 14, 393 (2004). – reference: 2) Bielawski, C. W., Wilson, C. G., “Macromolecular Engineering,” eds. by Matyjaszewski, K., Gnanou, Y., Leibler, L., Wiley-VCH, Weinheim (2007), Part 4, Chap. 7, pp. 2263-2293. – reference: 8) Miteva, T., Meisel, A., Knoll, W., Nothofer, H. G., Scherf, U., Müller, D. C., Meerholz, K., Yasuda, A., Neher, D., Adv. Mater., 13, 565 (2001). – reference: 5) Li, C., Liu, M., Pschirer, N. G., Baumgarten, M., Müllen, K., Chem. Rev., 110, 6817 (2010). – reference: 37) Naka, K., Uemura, T., Chujo, Y., Macromolecules, 33, 6965 (2000). – reference: 15) Nomura, K., Yamamoto, N., Ito, R., Fujiki, M., Geerts, Y., Macromolecules, 41, 4245 (2008). – reference: 22) Yamamoto, N., Ito, R., Geerts, Y., Nomura, K., Macromolecules, 42, 5104 (2009). – reference: 18) Baughman, T. W., Wagener, K. B., “Metathesis Polymerization,” ed. by Buchmeiser, M. R., Springer, Heidelberg (2005), p. 1. |
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| Title | モリブデン錯体触媒を用いる非環式ジエンメタセシス重合とWittig型カップリング反応による末端官能基化π共役ポリマーのone-pot精密合成 |
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