Mechanophores with a Reversible Radical System and Freezing-Induced Mechanochemistry in Polymer Solutions and Gels†
Dr. Keiichi Imato
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorAtsushi Irie
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorTakahiro Kosuge
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorDr. Tomoyuki Ohishi
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorDr. Masamichi Nishihara
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Atsushi Takahara
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Atsushi Takahara, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Hideyuki Otsuka, Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Hideyuki Otsuka
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Atsushi Takahara, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Hideyuki Otsuka, Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorDr. Keiichi Imato
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorAtsushi Irie
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorTakahiro Kosuge
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorDr. Tomoyuki Ohishi
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorDr. Masamichi Nishihara
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Atsushi Takahara
Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Atsushi Takahara, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Hideyuki Otsuka, Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Hideyuki Otsuka
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Atsushi Takahara, Graduate School of Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 (Japan)
Hideyuki Otsuka, Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550 (Japan)
Search for more papers by this authorThis work was supported by the Funding Program for Next Generation World-Leading Researchers (No. GR077) from Japan Society of the Promotion of Science (JSPS), JSPS KAKENHI (No. 26288057 and No. 26620175), and JSPS Research Fellowships for Young Scientists (No. 24⋅7074).
Graphical Abstract
Freezing-induced mechanochemistry: A new diarylbibenzofuranone-based mechanophore showed reversible color change by external forces through radical mechanism. By incorporating the mechanophore into polymer chains, it was revealed that freezing gels induced mechanical force along the chains, but the force was not large enough to cleave common covalent bonds.
Abstract
Visualization and quantitative evaluation of covalent bond scission in polymeric materials are highly important for understanding failure, fatigue, and deterioration mechanisms and improving the lifetime, durability, toughness, and reliability of the materials. The diarylbibenzofuranone-based mechanophore radical system enabled, through electron paramagnetic resonance spectroscopy, in situ quantitative evaluation of scission of the mechanophores and estimation of mechanical energy induced along polymer chains by external forces. The coagulation of polymer solutions by freezing probably generated force but did not cleave the mechanophores. On the other hand, cross-linking led to efficient propagation of the force of more than 80 kJ mol−1 to some mechanophores, resulting their cleavage and generation of colored stable radicals. This mechanoprobe concept has the potential to elucidate other debated issues in the polymer field as well.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie_201412413_sm_miscellaneous_information.pdf11.2 MB | miscellaneous_information |
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
- 1S.-Y. Cho, J.-G. Kim, C.-M. Chung, Sens. Actuators B 2008, 134, 822–825.
- 2D. A. Davis, A. Hamilton, J. Yang, L. D. Cremar, D. Van Gough, S. L. Potisek, M. T. Ong, P. V. Braun, T. J. Martínez, S. R. White, et al., Nature 2009, 459, 68–72.
- 3N. Bruns, K. Pustelny, L. M. Bergeron, T. A. Whitehead, D. S. Clark, Angew. Chem. Int. Ed. 2009, 48, 5666–5669; Angew. Chem. 2009, 121, 5776–5779.
- 4M. M. Caruso, D. A. Davis, Q. Shen, S. A. Odom, N. R. Sottos, S. R. White, J. S. Moore, Chem. Rev. 2009, 109, 5755–5798.
- 5C. M. Kingsbury, P. A. May, D. A. Davis, S. R. White, J. S. Moore, N. R. Sottos, J. Mater. Chem. 2011, 21, 8381–8388.
- 6Y. Chen, A. J. H. Spiering, S. Karthikeyan, G. W. M. Peters, E. W. Meijer, R. P. Sijbesma, Nat. Chem. 2012, 4, 559–562.
- 7C. E. Diesendruck, B. D. Steinberg, N. Sugai, M. N. Silberstein, N. R. Sottos, S. R. White, P. V. Braun, J. S. Moore, J. Am. Chem. Soc. 2012, 134, 12446–12449.
- 8M. B. Larsen, A. J. Boydston, J. Am. Chem. Soc. 2013, 135, 8189–8192.
- 9R. T. M. Jakobs, S. Ma, R. P. Sijbesma, ACS Macro Lett. 2013, 2, 613–616.
- 10A. L. B. Ramirez, Z. S. Kean, J. A. Orlicki, M. Champhekar, S. M. Elsakr, W. E. Krause, S. L. Craig, Nat. Chem. 2013, 5, 757–761.
- 11E. Ducrot, Y. Chen, M. Bulters, R. P. Sijbesma, C. Creton, Science 2014, 344, 186–189.
- 12B. Baytekin, H. T. Baytekin, B. A. Grzybowski, Angew. Chem. Int. Ed. 2014, 53, 6946–6950; Angew. Chem. 2014, 126, 7066–7070.
- 13D. W. R. Balkenende, S. Coulibaly, S. Balog, Y. C. Simon, G. L. Fiore, C. Weder, J. Am. Chem. Soc. 2014, 136, 10493–10498.
- 14K. L. Berkowski, S. L. Potisek, C. R. Hickenboth, J. S. Moore, Macromolecules 2005, 38, 8975–8978.
- 15C. R. Hickenboth, J. S. Moore, S. R. White, N. R. Sottos, J. Baudry, S. R. Wilson, Nature 2007, 446, 423–427.
- 16A. Piermattei, S. Karthikeyan, R. P. Sijbesma, Nat. Chem. 2009, 1, 133–137.
- 17J. M. Lenhardt, A. L. Black, S. L. Craig, J. Am. Chem. Soc. 2009, 131, 10818–10819.
- 18J. M. Lenhardt, M. T. Ong, R. Choe, C. R. Evenhuis, T. J. Martinez, S. L. Craig, Science 2010, 329, 1057–1060.
- 19H. M. Klukovich, Z. S. Kean, S. T. Iacono, S. L. Craig, J. Am. Chem. Soc. 2011, 133, 17882–17888.
- 20H. M. Klukovich, Z. S. Kean, A. L. B. Ramirez, J. M. Lenhardt, J. Lin, X. Hu, S. L. Craig, J. Am. Chem. Soc. 2012, 134, 9577–9580.
- 21Z. S. Kean, Z. Niu, G. B. Hewage, A. L. Rheingold, S. L. Craig, J. Am. Chem. Soc. 2013, 135, 13598–13604.
- 22C. K. Lee, C. E. Diesendruck, E. Lu, A. N. Pickett, P. A. May, J. S. Moore, P. V. Braun, Macromolecules 2014, 47, 2690–2694.
- 23K. B. Åbbas, R. S. Porter, J. Polym. Sci., Polym. Chem. Ed. 1976, 14, 553–564.
- 24K. B. Åbbas, T. Kirschner, R. S. Porter, Eur. Polym. J. 1978, 14, 361–367.
- 25V. Lozinsky, L. Domotenko, E. Vainerman, A. Mamtsis, S. Rogozhin, Polym. Bull. 1986, 15, 333–340.
- 26T. Q. Nguyen, Polym. Degrad. Stab. 1994, 46, 99–111.
- 27V. Zysman, T. Q. Nguyen, H.-H. Kausch, J. Polym. Sci. Part B 1994, 32, 1257–1269.
- 28R. Qian, J. Shen, N. Bei, C. Bai, C. Zhu, X. Wang, Macromol. Chem. Phys. 1996, 197, 2165–2174.
- 29S. Wang, X. Yan, J. Ding, M. Liu, R. Cheng, C. Wu, R. Qian, J. Macromol. Sci., Phys. 1997, 36, 187–194.
- 30H. Yang, R. Cheng, H. Xie, Z. Wang, Polymer 2005, 46, 7557–7562.
- 31F. Gu, H. Bu, Z. Zhang, Macromol. Chem. Phys. 1998, 199, 2597–2600.
10.1002/(SICI)1521-3935(19981101)199:11<2597::AID-MACP2597>3.0.CO;2-Z CAS Web of Science® Google Scholar
- 32F. Gu, H. Bu, Z. Zhang, Polymer 2000, 41, 7605–7609.
- 33M. Frenette, C. Aliaga, E. Font-Sanchis, J. C. Scaiano, Org. Lett. 2004, 6, 2579–2582.
- 34K. Imato, M. Nishihara, T. Kanehara, Y. Amamoto, A. Takahara, H. Otsuka, Angew. Chem. Int. Ed. 2012, 51, 1138–1142; Angew. Chem. 2012, 124, 1164–1168.
- 35M. Nishihara, K. Imato, A. Irie, T. Kanehara, A. Kano, A. Maruyama, A. Takahara, H. Otsuka, Chem. Lett. 2013, 42, 377–379.
- 36K. Imato, T. Ohishi, M. Nishihara, A. Takahara, H. Otsuka, J. Am. Chem. Soc. 2014, 136, 11839–11845.
- 37J. C. Scaiano, A. Martin, G. P. A. Yap, K. U. Ingold, Org. Lett. 2000, 2, 899–901.
- 38E. V. Bejan, E. Font-Sanchis, J. C. Scaiano, Org. Lett. 2001, 3, 4059–4062.
- 39M. Frenette, P. D. MacLean, L. R. C. Barclay, J. C. Scaiano, J. Am. Chem. Soc. 2006, 128, 16432–16433.
- 40S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 2003, 36, 255–263.
- 41T. Steiner, Angew. Chem. Int. Ed. 2002, 41, 48–76; Angew. Chem. 2002, 114, 50–80.
