Abstract
Ynone-based microporous polymer networks (YMPNs) were synthesized by the reaction of aromatic dicarboxylic acid chloride and alkyne groups under Sono-gashira cross-coupling reaction conditions. As the reaction proceeded in a mixture of toluene and triethylamine (TEA), tubular precipitates formed rapidly. The microscopic and XRD studies showed thatthe precipitates had a core-shell structure with a rod-shaped triethylammonium chloride (TEA-HC1) crystalline core and a polymeric shell. The core was removed by washing with methanol to provide a hollow polymeric tube. The TEA-HC1 rod formed in situ during the cross-coupling reaction and served as a template in forming the tubular morphology. YMPNs could be modified with ease because of the presence of highly reactive ynone groups. YMPNs were functionalized with ethylenediamine by the Michael-type addition reaction. The amino group functionalized YMPNs were used as precursors of nitrogen-doped porous carbons. The pyrolysis of the polymers at 800 °C produced microporous carbon materials withoutthe activation process. The carbon materials showed significantly enhanced Brunauer-Emmett-Teller (BET) surface areas and CO2 uptake capacities compared to their precursor polymers.
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References
R. Dawson, D. J. Adams, and A. I. Cooper, Chem. Sci., 2, 1173 (2011).
S. Kim and Y. M. Lee, Prog. Polym. Sci., 43, 1 (2015).
Y. Xie, T. T. Wang, X. H. Liu, K. Zou and W. Q. Deng, Nat Commun., 4, 1960 (2013).
Z.-D. Ding W. Zhu, T. Li, R. Shen, Y. Li, Z. Li, X. Ren and Z.-G. Gu, Dalt Trans., 46, 11372 (2017).
J. G. Kim, J. Lee, J. Lee, S. I. Jo, and J. Y. Chang Macromol. Res., 25, 629 (2017).
S. Ren, R. Dawson, D. J. Adams, and A. I. Cooper, Polym. Chem., 4, 5585 (2013).
B. Bonillo, R. S. Sprickand A. I. Cooper, Chem. Mater, 28, 3469 (2016).
Z. Xiao, M. Zhang W. Fan, Y. Qian, Z. Yang, B. Xu, Z. Kang, R. Wang and D. Sun, Chem. Eng. J., 326, 640 (2017).
L. Cai, Y. Li, Y. Li, H. Wang Y. Yu, Y. Liu, and Q. Duan, J. Hazard. Mater, 348, 47 (2018).
A. S. Karpovand T. J. J. Muller, Synthesis, 5, 2815 (2003).
Z. Li, J. He, X. Chen, Y. Cheng and J. Yang Tetrahedron, 74, 6612 (2018).
R. E. Whittaker, A. Dermenci, and G. Dong Synthesis, 48, 161 (2016).
H. Deng, R. Hu, A. C. S. Leung E. Zhao, J. W. Y. Lam, and B. Z. Tang Polym. Chem., 6, 4436 (2015).
H. Deng Z. He, J. W. Y. Lam, and B. Z. Tang Polym. Chem., 6, 8297 (2015).
C. Zheng, H. Deng, Z. Zhao, A. Qin, R. Hu, and B. Z. Tang Macromolecules, 48, 1941 (2015).
X. Tang, C. Zheng Y. Chen, Z. Zhao, A. Qin, R. Hu, and B. Z. Tang Macro-molecules, 49, 9291 (2016).
J. Choi, J. H. Ko, C. W. Kang, S. M. Lee, H. J. Kim, Y. J. Ko, M. Yang and S. U. Son, J. Mater. Chem. A, 6, 6233 (2018).
M. H. Kim, J. Choi, K. C. Ko, K. Cho, J. H. Park, S. M. Lee, H. J. Kim, Y. J. Ko, J. Y. Lee, and S. U. Son, Chem. Commun., 54, 5134 (2018).
A. Rehman and S. J. Park, Macromol. Res., 25, 1035 (2017).
D. Kim, S. Yun, S. Chun, and J. Choi, Macromol. Res., 26, 317 (2018).
H. Lim, M. C. Cha, and J. Y. Chang Macromol. Chem. Phys., 213, 1385 (2012).
P. Arab, M. G. Rabbani, A. K. Sekizkardes, T. Islamoglu, and H. M. El-Kaderi, Chem. Mater, 26, 1385 (2014).
R. Dawson, E. Stöckel, J. R. Hoist, D. J. Adams, and A. I. Cooper, Energy Environ. Sci., 4, 4239 (2011).
J. X. Jiang F. Su, A. Trewin, C. D. Wood, N. L. Campbell, H. Niu, C. Dickinson, A. Y. Ganin, M. J. Rosseinsky, Y. Z. Khimyak, and A. I. Cooper, Angew. Chem. Int Ed., 46, 8574 (2007).
R. J. Cox, D. J. Ritson, T. A. Dane, J. Berge, J. P. H. Charmant, and A. Kantacha, Chem. Commun., 1037 (2005).
S. Razzaque, C. Cai, Q. Lu, F. Huang, Y. Li, H. Tang I. Hussain, and B. Tan, J. Mater. Chem. B, 5, 742 (2017).
B. Li, X. Yang L. Xia, M. I. Majeed, and B. Tan, Sci. Rep., 3, 1 (2013).
N. Kang J. H. Park, M. Jin, N. Park, S. M. Lee, H. J. Kim, J. M. Kim, and S. U. Son, J. Am. Chem. Soc. 135, 19115 (2013).
Y. Lim, M. C. Cha, and J. Y. Chang Sci. Rep., 5, 15957 (2015).
Y. Chen, H. Sun, R. Yang, T. Wang, C. Pei, Z. Xiang, Z. Zhu, W. Liang A. Li, and W. Deng, J. Mater. Chem. A, 3, 87 (2015).
J. Chun, J. H. Park, J. Kim, S. M. Lee, H. J. Kim, and S. U. Son, Chem. Mater, 24, 3458 (2012).
J. Lee and J. Y. Chang RSC Adv, 8, 25277 (2018).
T. E. Glotova, M. Y. Dvorko, I.A. Ushakov, N. N. Chipanina, O. N. Kazheva, A. N. Chekhlov, O. A. Dyachenko, N. K. Gusarova, and B. A. Trofimov, Tetrahedron, 65, 9814 (2009).
W. Lu, Z. Wei, D. Yuan, J. Tian, S. Fordham, and H. C. Zhou, Chem. Mater., 26, 4589 (2014).
B. Kiskan and J. Weber, ACS Macro Lett., 1, 37 (2012).
S. Li, K. Han, J. Li, M. Li, and C. Lu, Micropor. Mesopor. Mater, 243, 291 (2017).
P. Puthiaraj, Y. R. Lee, and W. S. Ahn, Chem. Eng. J., 319, 65 (2017).
M. H. Nematollahi, A. H. S. Dehaghani, V. Pirouzfar, and E. Akhondi, Macromol Res., 24, 782 (2016).
R. Bera, S. Mondal, and N. Das, Micropor. Mesopor. Mater, 257, 253 (2018).
P. Markewitz, W. Kuckshinrichs, W. Leitner, J. Linssen, P. Zapp, R. Bongartz, A. Schreiber, and T. E. Mtiller, Energy Environ. Sci., 5, 7281 (2012).
J. Kou and L.-B. Sun, J. Mater. Chem. A, 4, 17299 (2016).
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Acknowledgments: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (No. 2015R1A2A2A01006585).
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Lee, J., Chang, J.Y. Synthesis and Functionalization of Ynone-Based Tubular Microporous Polymer Networks and Their Carbonized Products for CO2 Capture. Macromol. Res. 27, 991–997 (2019). https://doi.org/10.1007/s13233-019-7145-x
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DOI: https://doi.org/10.1007/s13233-019-7145-x