Abstract
Microporous hypercross-linked conjugated quinonoid chromophores represent a novel class of amorphous polymers, synthesized by the reaction of anthracene with dimethoxy methane in the presence of FeCl3 catalyst. Their N2 adsorption isotherms confirm their microporous nature. Diffuse reflectance UV-Visible (DRS UV-Vis) spectroscopy confirms their matrix built with the conjugated quinonoids by their broad light absorption characteristics extending from 1000 nm to 200 nm with the absorbance maximum close to 400 nm. The catalyst cross-linked anthracene with -CH2- bridges and subsequently dehydrogenating them to form quinonoids. Their Fourier transform infrared (FTIR) spectra showed their characteristic quinonoid vibrations between 1600 and 1700 cm−1. The synthesis of polymers was carried out at 30, 40, 50, 60, 70 and 80 °C, but the quinonoid content of the polymer obtained at 80 °C was higher than that of the others. Their scanning electron microscopy (SEM) images showed microspheres of 1 to 5 μm size built with tiny particles. Their surfaces were not smooth. The polymer synthesized at 80 °C showed 5.1 wt% CO2 sorption at 25 °C and 0.1 MPa, but when it was recross-linked, the CO2 sorption increased to 8 wt%. Hence, hypercross-linked conjugated quinonoid chromophores of anthracene are good for sorption of CO2.
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Karl, T.R. and Trenberth, K.E., Science, 2003, 302: 1719
Vinodh, R., Hemalatha, P., Ganesh, M., Peng, M.M., Abidov, A., Palanichamy, M., Cha, W.S. and Jang, H.T., RSC Advances, 2014, 4: 3668
Cote, A.P., Benin, A.I., Ockwig, N.W., O’Keeffe, M., Matzger, A.J. and Yaghi, O.M., Science, 2005, 310: 1166
Cote, A.P., El-Kaderi, H.M., Furukawa, K., Hunt, J.R. and Yaghi, O.M., J. Am. Chem. Soc., 2007, 129: 12914
Kuhn, P., Antonietti, P. and Thomas, A., Angew. Chem. Int. Ed., 2008, 47: 3450
Bojdys, M.J., Jeromenok, J., Thomas, A. and Antonietti, M., Adv. Mater., 2010, 22: 2202
Zhang, S.M., Chang, Z., Hu, T.L. and Bu, X.H., Inorg. Chem., 2010, 49: 11581
Nugent, P.S., Rhodus, V.L., Pham, T., Forrest, K., Wojtas, L., Space, B. and Zaworotko, M.J., J. Am. Chem. Soc., 2013, 135: 10950
Leong, C.F., Faust, T.B., Turner, P., Usov, P.M., Kepert, C.J., Babarao, R., Thornton, A.W. and D’Alessandro, D.M., Dalton Trans., 2013, 42: 9831
Tsyurupa, M.P. and Davankov, V.A., React. Funct. Polym., 2006, 66: 768
Fang, W., Luo, L. and Jiang, J., Phys. Chem. Chem. Phys., 2013, 15: 651
Wu, D., Xu, F., Sun, B., Fu, R., He, H. and Matyjaszewski, K., Chem. Rev., 2012, 112: 3959
Budd, P.M., Ghanem, B.S., Makhseed, S., McKeown, N.B., Msayib, K.J. and Tattershall, C.E., Chem. Commun., 2004, 2: 230
McKeown, N.B., Budd, P.M., Msayib, K.J., Ghanem, B.S., Kingston, H.J., Tattershall, C.E., Makhseed, S., Reynolds, K.J. and Fritsch, D., Chem. Eur. J., 2005, 11: 2610
Li, Z., Wu, D., Liang, Y., Fu, R. and Matyjaszewski, K., J. Am. Chem. Soc., 2014, 136: 4805
Jonathan, G., Jean, M.J.F. and Frantisek, S., Small 2009, 5: 1098
Okay, O., Prog. Polym. Sci., 2000, 25: 711
Gokmen, M.T. and DuPrez, F.E., Prog. Polym. Sci., 2012, 37: 365
Duranoglu, D., Kaya, I.G., Beker, U. and Senkal, B.F., Chem. Engg. J., 2012, 103: 181
Jianhan, H., Li, Y., Xiaofei, W., Maowen, X., You-Nian, L. and Shuguang, D., Chem. Engg. J., 2013, 222: 1
Li, J.R., Yu, J., Lu, W., Sun, L.B., Sculley, J., Balbuena, P.B. and Zhou, H.C., Nat. Commun., in press
Liebl, M.R. and Senker, J., Chem. Mater., 2013, 25: 970
Lu, W., Yuan, D., Sculley, J., Zhao, D., Krishna, R. and Zhou, H.C., J. Am. Chem. Soc., 2011, 133: 18126
Ahmad, K., Mowla, O., Kennedy, E.M., Dlugogorski, B.Z., Mackie, J.C. and Stockenhuber, M., Energy Technol., 2013, 1: 345
Xu, C. and Hedin, N., J. Mater. Chem., 2013, 1: 3406
Lu, W., JSculley, J.P., Yuan, D., Krishna, R., Wei, Z. and Zhou, H.C., Angew. Chem. Int. Ed., 2012, 51: 1
Jeromenok, J., Bohlmann, W., Jager, C. and Weber, J., Chemistry Open, 2013, 2: 17
Didas, S.A., Kulkarni, A.R., Sholl. D.S. and Jones, C.W., Chem. Sus. Chem., 2012, 5: 2058
Kuwahara, Y., Kang, D.Y., Copeland, J.R., Bollini, P., Sievers, C., Kamegawa, T., Yamashita, H. and Jones, C.W., Chem. Eur. J., 2012, 18: 16649
Li, B., Gong, R., Wang, W., Huang, X., Zhang, W., Li, H., Hu, C. and Tan, B., Macromolecules, 2011, 44: 2410
Li, B., Huang, X., Liang, L. and Tan, B., J. Mater. Chem., 2010, 20: 7444
Luo, Y., Li, B., Wang, W., Bing, K. and Tan, B., Adv. Mater., 2012, 24: 5703
Lu, W., Sculley, J.P., Yuan, D., Krishna, R., Wei, Z. and Zhou, H.C., Angew. Chem. Int. Ed., 2012, 51: 1
Bickel, A.F. and Kooijman, E.C., Nature, 1952, 170: 211
Begona, M., Enrique, O., Victor, H., Juan, T.L.N. and Tetsuo, O., J. Phys. Chem. B, 2003, 107: 12175
Zhang, X., Jin, Q., Dai, L. and Yuan, S., Bull. Mater. Sci., 2011, 34: 735
Davankov, V.A., Ragozhin, S.V. and Tsyurpa, M.P., 1971, U.S. Pat., 3729457
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This work was financially supported by the Korea CCS R&D Centre, funded by the Ministry of Education, Science and Technology of the Korean Government.
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Vinodh, R., Ganesh, M., Peng, M.M. et al. Microporous hypercross-linked conjugated quinonoid chromophores of anthracene: Novel polymers for CO2 adsorption. Chin J Polym Sci 33, 224–235 (2015). https://doi.org/10.1007/s10118-015-1573-7
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DOI: https://doi.org/10.1007/s10118-015-1573-7