

FOLLOWUS
a.Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering; University of Jinan, Jinan 250022, China
b.Nutrition & Health Research Institute, COFCO Corporation, Beijing Key Laboratory of Nutrition & Health and Food Safety, Beijing 102209, China
chm_panqw@ujn.edu.cn (Q.W.P.)
xieyunfeng@cofco.com (Y.F.X.)
chm_chenzy@ujn.edu.cn (Z.Y.C.)
Received:31 July 2021,
Revised:2021-11-17,
Accepted:18 November 2021,
Online First:14 January 2022,
Published:01 March 2022
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Duan, Z. Y.; Wang, Y. Y.; Pan, Q. W.; Xie, Y. F.; Chen, Z. Y. Hypercrosslinking polymers fabricated from divinyl benzene via Friedel-Crafts addition polymerization. Chinese J. Polym. Sci. 2022, 40, 310–320
Zheng-Yu Duan, Yan-Yan Wang, Qi-Wei Pan, et al. Hypercrosslinking Polymers Fabricated from Divinyl Benzene
Duan, Z. Y.; Wang, Y. Y.; Pan, Q. W.; Xie, Y. F.; Chen, Z. Y. Hypercrosslinking polymers fabricated from divinyl benzene via Friedel-Crafts addition polymerization. Chinese J. Polym. Sci. 2022, 40, 310–320 DOI: 10.1007/s10118-022-2667-7.
Zheng-Yu Duan, Yan-Yan Wang, Qi-Wei Pan, et al. Hypercrosslinking Polymers Fabricated from Divinyl Benzene
Microporous organic polymers with high surface area are widely used in many applications. Among them
hypercrosslinked polymers have been extensively concerned because of their simple processes and low-cost reagents. However
due to most state-of-the-art strategies for HCPs based on condensation reactions
the release of small molecules such as hydrochloric acid and methanol involved in such strategies brings about new hazards to environment. Herein
we propose a method of fabrication of hypercrosslinked polymers
via
self-addition polymerization of divinyl benzene and its crosslinking with polar aromatic molecules. The hypercrosslinked polyDVB-based products are demonstrated by Friedel-Crafts addition reaction of double bonds on DVB that can connect adjacent phenyl rings of aromatic molecules to form the crosslinked networks. The HCPDVB-CB obtained in 1-chlorobutane as solvent has a high micropore content and displays high surface area up to 931 m
2
/g. Following this finding
DVB is used as a novel external crosslinker for knitting polar aromatic molecules. When L-phenylalanine and bisphenol A are used as the aromatic units
the obtained HCP(Phe-DVB) and HCP(BPA-DVB) could reach surface area of 612 and 471 m
2
/g
and have hydrogen uptake of 0.62 wt% and 0.58 wt% at 77 K and 1.13 bar by comparison with HCPDVB-CB having hydrogen uptake of 0.30 wt%
respectively.
Zhu, J. Y.; Yuan, S. S.; Wang, J.; Zhang, Y. T.; Tian, M. M.; Bruggen, B. V . Microporous organic polymer-based membranes for ultrafast molecular separations . Prog. Polym. Sci. , 2020 . 110 101308 DOI: 10.1016/j.progpolymsci.2020.101308 http://doi.org/10.1016/j.progpolymsci.2020.101308 .
Du, M. Q.; Peng, Y. Z.; Ma, Y. C.; Yang, L.; Zhou, Y. L.; Zeng, F. K.; Wang, X. K.; Song, M. L.; Chang, G. J . Selective carbon dioxide capture in antifouling indole-based microporous organic polymers . Chinese J. Polym. Sci. , 2020 . 38 187 - 194 . DOI: 10.1007/s10118-019-2326-9 http://doi.org/10.1007/s10118-019-2326-9 .
Das, S.; Heasman, P.; Ben, T.; Qiu, S. L . Porous organic materials: strategic design and structure-function correlation . Chem. Rev. , 2017 . 117 1515 - 1563 . DOI: 10.1021/acs.chemrev.6b00439 http://doi.org/10.1021/acs.chemrev.6b00439 .
Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O’Keeffe, M.; Matzger, A. J.; Yaghi, O. M . Porous, crystalline, covalent organic frameworks . Science , 2005 . 310 1166 - 1170 . DOI: 10.1126/science.1120411 http://doi.org/10.1126/science.1120411 .
Hu, X. L.; Li, H. G.; Tan, B. E . COFs-based porous materials for photocatalytic applications . Chinese J. Polym. Sci. , 2020 . 38 673 - 684 . DOI: 10.1007/s10118-020-2394-x http://doi.org/10.1007/s10118-020-2394-x .
Wang, M. Y.; Zhang, Q. J.; Shen, Q. Q.; Li, Q. Y.; Ren, S. J . Truxene-based conjugated microporous polymers via different synthetic methods . Chinese J. Polym. Sci. , 2020 . 38 151 - 157 . DOI: 10.1007/s10118-019-2321-1 http://doi.org/10.1007/s10118-019-2321-1 .
Lei, Y.; Tian, Z. Y.; Sun, H. X.; Liu, F.; Zhu, Z. Q.; Liang, W. D.; Li, A . Low-resistance thiophene-based conjugated microporous polymer nanotube filters for efficient particulate matter capture and oil/water separation . ACS Appl. Mater. Interfaces , 2021 . 13 5823 - 5833 . DOI: 10.1021/acsami.0c20484 http://doi.org/10.1021/acsami.0c20484 .
Kuhn, P.; Antonietti, M.; Thomas, A . Porous, covalent triazine-based frameworks prepared by ionothermal synthesis . Angew. Chem. Int. Ed. , 2008 . 47 3450 - 3453 . DOI: 10.1002/anie.200705710 http://doi.org/10.1002/anie.200705710 .
Kamiya, K . Selective single-atom electrocatalysts: a review with a focus on metal-doped covalent triazine frameworks . Chem. Sci. , 2020 . 11 8339 - 8349 . DOI: 10.1039/D0SC03328F http://doi.org/10.1039/D0SC03328F .
Ben, T.; Ren, H.; Ma, S. Q.; Cao, D. P.; Lan, J. H.; Jing, X. F.; Wang, W. C.; Xu, J.; Deng, F.; Simmons, J. M.; Qiu, S. L.; Zhu, G. S . Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area . Angew. Chem. Int. Ed. , 2009 . 48 9457 - 9460 . DOI: 10.1002/anie.200904637 http://doi.org/10.1002/anie.200904637 .
Shen, Y. M.; Xue, Y.; Yan, M.; Mao, H. L.; Cheng, H.; Chen, Z.; Sui, Z. W.; Zhu, S. B.; Yu, X. J.; Zhuang, J. L . Synthesis of TEMPO radical decorated hollow porous aromatic frameworks for selective oxidation of alcohols . Chem. Commun. , 2021 . 57 907 - 910 . DOI: 10.1039/D0CC06965E http://doi.org/10.1039/D0CC06965E .
Jung, D.; Chen, Z. J.; Alayoglu, S.; Mian, M. R.; Goetjen, T. A.; Idrees, K. B.; Kirlikovali, K. O.; Islamoglu, T.; Farha, O. K . Postsynthetically modified polymers of intrinsic microporosity (PIMs) for capturing toxic gases . ACS Appl. Mater. Interfaces , 2021 . 13 10409 - 10415 . DOI: 10.1021/acsami.0c21741 http://doi.org/10.1021/acsami.0c21741 .
Tozawa, T.; Jones, J. T. A.; Swamy, S. I.; Jiang, S.; Adams, D. J.; Shakespeare, S.; Clowes, R.; Bradshaw, D.; Hasell, T.; Chong, S. Y.; Tang, C.; Thompson, S.; Parker, J.; Trewin, A.; Bacsa, J.; Slawin, A. M. Z.; Steiner, A.; Cooper, A. I . Porous organic cages . Nat. Mater. , 2009 . 8 973 - 978 . DOI: 10.1038/nmat2545 http://doi.org/10.1038/nmat2545 .
Webstet, O. W.; Gentry, F. P.; Farlee, R. D.; Smart, B. E . Hypercrosslinked rigid-rod polymers . Makromol. Chem. Macromol. Symp. , 1992 . 54 477 - 482 . .
Li, J. Q.; Wang, Z.; Wang, Q. Q.; Guo, L. Y.; Wang, C.; Wang, Z.; Zhang, S. H.; Wu, Q. H . Construction of hypercrosslinked polymers for high-performance solid phase microextraction of phthalate esters from water samples . J. Chromatogr. A , 2021 . 1641 461972 DOI: 10.1016/j.chroma.2021.461972 http://doi.org/10.1016/j.chroma.2021.461972 .
Fontanals, N.; Marcé, R. M.; Borrulla, F.; Cormack, P. A. G . Hypercrosslinked materials: preparation, characterisation and applications . Polym. Chem. , 2015 . 6 7231 - 7244 . DOI: 10.1039/C5PY00771B http://doi.org/10.1039/C5PY00771B .
Tan, L. X.; Tan, B. E . Hypercrosslinked porous polymer materials: design, synthesis, and applications . Chem. Soc. Rev. , 2017 . 46 3322 - 3356 . DOI: 10.1039/C6CS00851H http://doi.org/10.1039/C6CS00851H .
Tan, L. X.; Tan, B. E . Research progress in hypercrosslinked microporous organic polymers . Acta Chimica Sinica (in Chinese) , 2015 . 73 530 - 540 . DOI: 10.6023/A15020096 http://doi.org/10.6023/A15020096 .
Davankov, V.; Tsyurupa, M.; Ilyin, M.; Pavlova, L . Hypercross-linked polystyrene and its potentials for liquid chromatography: a mini-review . J. Chromatogr. A , 2002 . 965 65 - 73 . DOI: 10.1016/S0021-9673(01)01583-7 http://doi.org/10.1016/S0021-9673(01)01583-7 .
Davankov, V. A.; Rogozhin, S. V.; Tsyurupa, M. P.; 1973 , U.S. Pat.; 3,729,457
Hradil, J.; Králová, E . Styrene-divinylbenzene copolymers post-crosslinked with tetrachloromethane . Polymer , 1998 . 39 6041 - 6048 . DOI: 10.1016/S0032-3861(98)00057-3 http://doi.org/10.1016/S0032-3861(98)00057-3 .
Macintyre, F. S.; Sherrington, D. C.; Tetley. L . Synthesis of ultrahigh surface area monodisperse porous polymer nanospheres . Macromolecules , 2006 . 39 5381 - 5384 . DOI: 10.1021/ma0610010 http://doi.org/10.1021/ma0610010 .
Wood, C. D.; Tan, B. E.; Trewin, A.; Niu, H. J.; Bradshaw, D.; Rosseinsky, M. J.; Khimyak, Y. Z.; Campbell, N. L.; Kirk, R.; Stöckel E.; Cooper, A. I . Hydrogen storage in microporous hypercrosslinked organic polymer networks . Chem. Mater. , 2007 . 19 2034 - 2048 . DOI: 10.1021/cm070356a http://doi.org/10.1021/cm070356a .
Luo, Y. L.; Zhang, S. C.; Ma, Y. X.; Wang, W.; Tan, B. E . Microporous organic polymers synthesized by self-condensation of aromatic hydroxymethyl monomers . Polym. Chem. , 2013 . 4 1126 - 1131 . DOI: 10.1039/C2PY20914D http://doi.org/10.1039/C2PY20914D .
Woodward, R. T . The design of hypercrosslinked polymers from benzyl ether self-condensing compounds and external crosslinkers . Chem. Commun. , 2020 . 56 4938 - 4941 . DOI: 10.1039/D0CC01002B http://doi.org/10.1039/D0CC01002B .
Li, B. Y.; Gong, R. N.; Wang, W.; Huang, X.; Zhang, W.; Li, H. M.; Hu, C. X.; Tan, B. E . A new strategy to microporous polymers: knitting rigid aromatic building blocks by external cross-linker . Macromolecules , 2011 . 44 2410 - 2414 . DOI: 10.1021/ma200630s http://doi.org/10.1021/ma200630s .
Wang, S. L.; Zhang, C. X.; Shu, Y.; Jiang, S. L.; Xia, Q.; Chen, L. J.; Jin, S. B.; Hussain, I.; Cooper A. I.; Tan, B. E . Layered microporous polymers by solvent knitting method . Sci. Adv. , 2017 . 3 e1602610 DOI: 10.1126/sciadv.1602610 http://doi.org/10.1126/sciadv.1602610 .
Wilson, A. S. S.; Hill, M. S.; Mahon, M . F.; Dinoi, C.; Maron, L. Organocalcium-mediated nucleophilic alkylation of benzene . Science , 2017 . 358 1168 - 1171 . DOI: 10.1126/science.aao5923 http://doi.org/10.1126/science.aao5923 .
Gilman, H.; Meals, R . Rearrangements in the Friedel-Crafts alkylation of benzene . J. Org. Chem. , 2002 . 8 126 - 146 . .
Rueping, M.; Nachtsheim, B. J . A review of new developments in the Friedel-Crafts alkylation from green chemistry to asymmetric catalysis . Beilstein J. Org. Chem. , 2010 . 6 6 DOI: 10.3762/bjoc.6.6 http://doi.org/10.3762/bjoc.6.6 .
Soukupová, K.; Sassi, A.; Jeřábek, K . Reinforcing of expanded polymer morphology using peroxy radical initiator . React. Funct. Polym. , 2009 . 69 353 - 357 . DOI: 10.1016/j.reactfunctpolym.2009.02.008 http://doi.org/10.1016/j.reactfunctpolym.2009.02.008 .
Li, L.; Zhang, A. J.; Yu, J. H.; Li, W . Q.; Gao, H.; Tian, K.; Bai, H. One-step preparation of hierarchically porous polyureas: simultaneous foaming and hyper-crosslinking . Polymer , 2017 . 108 332 - 338 . DOI: 10.1016/j.polymer.2016.11.002 http://doi.org/10.1016/j.polymer.2016.11.002 .
Xia, Y. X.; Di, T.; Meng, Z. H.; Zhu, T. T.; Lei, Y. J.; Chen, S.; Li, T. S.; Li, L . Versatile one-pot construction strategy for the preparation of porous organic polymers via domino polymerization . Macromolecules , 2021 . 54 4682 - 4692 . DOI: 10.1021/acs.macromol.1c00473 http://doi.org/10.1021/acs.macromol.1c00473 .
Liu, W. H.; Wang, J. T.; Liu, J. J.; Hou, F. Y.; Wu, Q . H.; Wang, C.; Wang, Z. Preparation of phenylboronic acid based hypercrosslinked polymers for effective adsorption of chlorophenols . J. Chromatogr. A , 2020 . 1628 461470 DOI: 10.1016/j.chroma.2020.461470 http://doi.org/10.1016/j.chroma.2020.461470 .
Ding, L.; Zhang, A. J.; Li, W . Q.; Bai, H.; Li, L. Multi-length scale porous polymer films from hypercrosslinked breath figure arrays . J. Colloid. Interface Sci. , 2016 . 461 179 - 184 . DOI: 10.1016/j.jcis.2015.09.031 http://doi.org/10.1016/j.jcis.2015.09.031 .
Yang, Y. W.; Tan, B. E.; Wood. C. D . Solution-processable hypercrosslinked polymers by low cost strategies: a promising platform for gas storage and separation . J. Mater. Chem. A , 2016 . 4 15072 - 15080 . DOI: 10.1039/C6TA05226F http://doi.org/10.1039/C6TA05226F .
Ando, K.; Ito, T.; Tesehima, H.; Kusano, H.; in Ion exchange for industry , Ed. by Streat, M.; Springer, Chichester, UK, 1988 , p. 232−238.
Zeng, X. W.; Yu, T. J.; Wang, P.; Yuan, R. H.; Wen, Q.; Fan, Y. G.; Wang, C. H.; Shi, R. F . Preparation and characterization of polar polymeric adsorbents with high surface for the removal of phenol from water . J. Hazard. Mater. , 2010 . 177 773 - 780 . DOI: 10.1016/j.jhazmat.2009.12.100 http://doi.org/10.1016/j.jhazmat.2009.12.100 .
Zeng, X. W.; Fan, Y. G.; Wu, G. L.; Wang, C. H.; Shi. R. F . Enhanced adsorption of phenol from water by a novel polar post-crosslinked polymeric adsorbent . J. Hazard. Mater. , 2009 . 169 1022 - 1028 . DOI: 10.1016/j.jhazmat.2009.04.044 http://doi.org/10.1016/j.jhazmat.2009.04.044 .
Guo, F. H.; Wang, Y. P.; Chen, X. L.; Chen, M. Q.; He, W.; Chen, Z. Y . Supermacroporous polydivinylbenzene cryogels with high surface area: synthesis by solvothermal postcrosslinking and their adsorption behaviors for carbon dioxide and aniline . J. Appl. Polym. Sci. , 2019 . 136 47716 DOI: 10.1002/app.47716 http://doi.org/10.1002/app.47716 .
Wu, Y.; Wang, D. X.; Li, L. G.; Yang, W. Y.; Feng, S. Y.; Liu, H. Z . Hybrid porous polymers constructed from octavinylsilsesquioxane and benzene via Friedel-Crafts reaction: tunable porosity, gas sorption, and postfunctionalization . J. Mater. Chem. A , 2014 . 2 2160 - 2167 . DOI: 10.1039/C3TA14746K http://doi.org/10.1039/C3TA14746K .
Shen, R.; Du, Y. J.; Yang, X. R.; Liu, H. Z . Silsesquioxanes-based porous functional polymers for water purification . J. Mater. Sci. , 2020 . 55 7518 - 7529 . DOI: 10.1007/s10853-020-04541-6 http://doi.org/10.1007/s10853-020-04541-6 .
He, J. X.; Zhao, G. H.; Mu, P.; Wei, H. J.; Su, Y. N.; Sun, H. X.; Zhu, Z. Q.; Liang, W. D.; Li, A . Scalable fabrication of monolithic porous foam based on cross-linked aromatic polymers for efficient solar steam generation . Sol. Energy Mater Sol. Cells , 2019 . 201 110111 DOI: 10.1016/j.solmat.2019.110111 http://doi.org/10.1016/j.solmat.2019.110111 .
Carraher, Jr., C. E.; in Polymer chemistry, Marcel Dekker, New York, 2003 , p. 36−53.
Chen, X. L.; Ding, Y. Y.; Ren, D. Y.; Chen, Z. Y . Green synthesis of polymeric microspheres that are monodisperse and superhydrophobic, via quiescent redox-initiated precipitation polymerization . RSC Adv. , 2016 . 6 27846 - 27851 . DOI: 10.1039/C5RA28153A http://doi.org/10.1039/C5RA28153A .
Huang, H. Q.; Ding, Y. Y.; Chen, X. L.; Chen, Z. Y.; Kong, X. Z . Synthesis of monodisperse micron-sized poly(divinylbenzene) microspheres by solvothermal precipitation polymerization . Chem. Eng. J. , 2016 . 289 135 - 141 . DOI: 10.1016/j.cej.2015.12.092 http://doi.org/10.1016/j.cej.2015.12.092 .
Hubbard, K. L.; Finch, J. A.; Darling, G. D . The preparation and characteristics of poly(divinylbenzene- co -ethylvinylbenzene), including Ambetilite XAD-4. Styrenic resins with pendant vinylbenzene groups . React. Funct. Polym. , 1998 . 36 17 - 30 . DOI: 10.1016/S1381-5148(97)00127-2 http://doi.org/10.1016/S1381-5148(97)00127-2 .
Okay, O . Macroporous copolymer networks . Prog. Polym. Sci. , 2000 . 25 711 - 779 . DOI: 10.1016/S0079-6700(00)00015-0 http://doi.org/10.1016/S0079-6700(00)00015-0 .
Dawson, R.; Cooper, A. I.; Adams, D. J . Nanoporous organic polymer networks . Prog. Polym. Sci. , 2012 . 37 530 - 563 . DOI: 10.1016/j.progpolymsci.2011.09.002 http://doi.org/10.1016/j.progpolymsci.2011.09.002 .
Ahn, J. H.; Jang, J. E.; Oh, C. G.; Ihm, S. K.; Cortez, J.; Sherrington, D. C . Rapid generation and control of microporosity, bimodal pore size distribution, and surface area in Davankov-Type hyper-cross-linked resins . Macromolecules , 2006 . 39 627 - 632 . DOI: 10.1021/ma051152n http://doi.org/10.1021/ma051152n .
Liu, Y.; Fan, X. L.; Jia, X. K.; Zhang, B. L.; Zhang, H. P.; Zhang, A. B.; Zhang, Q. Y . Hypercrosslinked polymers: controlled preparation and effective adsorption of aniline . J. Mater. Sci. , 2016 . 51 8579 - 8592 . DOI: 10.1007/s10853-016-0118-y http://doi.org/10.1007/s10853-016-0118-y .
Dawson, R.; Stevens, L. A.; Drage, T. C.; Snape, C. E.; Smith, M. W.; Adams, D. J.; Cooper, A. I . Porous organic alloys . J. Am. Chem. Soc. , 2012 . 134 10741 - 10744 . DOI: 10.1021/ja301926h http://doi.org/10.1021/ja301926h .
Law, R. V.; Sherrington, D. C.; Snape, C. E . Solid-state 13 C MAS NMR studies of hyper-cross-linked polystyrene resins . Macromolecules , 1996 . 29 6284 - 6293 . DOI: 10.1021/ma951606o http://doi.org/10.1021/ma951606o .
Liu, F.; Liang, W. D.; Wang, C. J.; He, J. X.; Xiao, C. H.; Zhu, Z. Q.; Sun, H. X.; Li, A . Superwetting monolithic hypercrosslinked polymers nanotubes with high salt-resistance for efficient solar steam generation . Sol. Energy Mater Sol. Cells , 2021 . 221 110913 DOI: 10.1016/j.solmat.2020.110913 http://doi.org/10.1016/j.solmat.2020.110913 .
Yan, Q.; Bai, Y. W.; Meng, Z.; Yang, W. T . Precipitation polymerization in acetic acid: synthesis of monodisperse cross-linked poly(divinylbenzene) microspheres . J. Phys. Chem. B , 2008 . 112 6914 - 6922 . DOI: 10.1021/jp711324a http://doi.org/10.1021/jp711324a .
Li, H. Y.; Meng, B.; Mahurin, S. M.; Chai, S. H.; Nelson, K. M.; Baker, D. C.; Liu, H. L.; Dai, S . Carbohydrate based hyper-crosslinked organic polymers with -OH functional groups for CO 2 separation . J. Mater. Chem. A , 2015 . 3 20913 - 20918 . DOI: 10.1039/C5TA03213J http://doi.org/10.1039/C5TA03213J .
Robshaw, T. J.; Jamesa, A. M.; Hammonda, D. B.; Reynolds, J.; Dawsona, R.; Ogden, M. D . Calcium-loaded hydrophilic hypercrosslinked polymers for extremely high defluoridation capacity via multiple uptake mechanisms . J. Mater. Chem. A , 2020 . 8 7130 - 7144 . DOI: 10.1039/C9TA12285K http://doi.org/10.1039/C9TA12285K .
Wu, Y.; Li, L. G.; Yang, W. Y.; Feng, S. Y.; Liu, H. Z . Hybrid nanoporous polystyrene derived from cubic octavinylsilsesquioxane and commercial polystyrene via the Friedel-Crafts reaction . RSC Adv. , 2015 . 5 12987 - 12993 . DOI: 10.1039/C4RA14830D http://doi.org/10.1039/C4RA14830D .
Yang, Z. Z.; Fu, S. Q.; Yan, C.; Yao, J. S.; Liu, W. L . Hyper-cross-linked polymers based on triphenylsilane for hydrogen storage and water treatment . J. Macromol. Sci. A , 2018 . 56 162 - 169 . .
Gao, H.; Ding, L.; Bai, H.; Liu, A. H.; Li, S. Z.; Li, L . Pitch-based hyper-cross-linked polymers with high performance for gas adsorption . J. Mater. Chem. A , 2016 . 4 16490 - 16498 . DOI: 10.1039/C6TA07033G http://doi.org/10.1039/C6TA07033G .
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