Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal

An-Qi Xiao; Xiao-Lin Lyu; Hong-Bing Pan; Zhe-Hao Tang; Wei Zhang; Zhi-Hao Shen; Xing-He Fan

doi:10.1007/s10118-020-2431-9

Your Location：

Home >

Browse articles >

Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal

ARTICLE | Updated：2020-06-19

- Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal
- Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal
- Chinese Journal of Polymer Science 2020年38卷第11期页码：1185-1191
- Affiliations：
  
  Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Center for Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
- Author bio：
  
  zshen@pku.edu.cn (Z.H.S.)
  fanxh@pku.edu.cn (X.H.F.)
- Funds：
  
  This work was financially supported by the National Key R&D Program of China (No. 2018YFB0703702) and the National Natural Science Foundation of China (No. 51725301). And the authors also gratefully acknowledge the scientists at beamline 1W2A at BSRF and at beamline BL16B1 at SSRF for their assistance on the synchrotron-radiation WAXS and MAXS experiments.
- DOI：10.1007/s10118-020-2431-9
  中图分类号：
- 收稿：2020-03-03，
  
  修回：2020-3-17，
  
  录用：2020-3-20，
  
  网络首发：2020-06-19，
  
  纸质出版：2020-08-14
- Accepted：
Scan QR Code
Xiao, A. Q.; Lyu, X. L.; Pan, H. B.; Tang, Z. H.; Zhang, W.; Shen, Z. H.; Fan, X. H. Homeotropic alignment and selective adsorption of nanoporous polymer film polymerized from hydrogen-bonded liquid crystal. Chinese J. Polym. Sci. 2020, 38, 1185–1191

An-Qi Xiao, Xiao-Lin Lyu, Hong-Bing Pan, et al. Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal[J]. Chinese Journal of Polymer Science, 2020, 38(11): 1185-1191.
Xiao, A. Q.; Lyu, X. L.; Pan, H. B.; Tang, Z. H.; Zhang, W.; Shen, Z. H.; Fan, X. H. Homeotropic alignment and selective adsorption of nanoporous polymer film polymerized from hydrogen-bonded liquid crystal. Chinese J. Polym. Sci. 2020, 38, 1185–1191 DOI： 10.1007/s10118-020-2431-9.

An-Qi Xiao, Xiao-Lin Lyu, Hong-Bing Pan, et al. Homeotropic Alignment and Selective Adsorption of Nanoporous Polymer Film Polymerized from Hydrogen-bonded Liquid Crystal[J]. Chinese Journal of Polymer Science, 2020, 38(11): 1185-1191. DOI： 10.1007/s10118-020-2431-9.

摘要

Abstract

Nanoporous polymer film with a hexagonal columnar (Col

) structure was fabricated by templated hydrogen-bonding discotic liquid crystals containing methacrylate functional group. The supramolecular hydrogen-bonded complex T3Ph-L is composed of a 1

5-tris(1

-benzo[

]imidazol-2-yl)benzene (T3Ph) core molecule as the hydrogen-bonding acceptor and 3

5-tris((11-(methacryloyloxy)undecyl)oxy)benzoic acid (L) peripheral molecules as donors. And the Col

structure is always retained after self-assembly

photo-crosslinking

and removal of the template T3Ph. The nanoporous polymer film can retain the Col

phase even under the dry condition

which indicates more possibilities for practical applications. After chemical modification of the inner wall of the nanopores

the nanoporous polymer film with pores of about 1 nm selectively adsorbs ionic dyes

and the adsorption process is spontaneous and exothermic in nature. Homeotropic alignment can be obtained when the blend complex was sandwiched between two modified glasses after annealing by slow cooling

which shows that the nanoporous polymer film has potential in applications such as nanofiltration.

关键词

Keywords

references

Sun, M. H.; Huang, S. Z.; Chen, L. H.; Li, Y.; Yang, X. Y.; Yuan, Z. Y.; Su, B. L. . Applications of hierarchically structured porous materials from energy storage and conversion, catalysis, photocatalysis, adsorption, separation, and sensing to biomedicine . Chem. Soc. Rev. , 2016 . 45 3479 - 3563 . DOI: 10.1039/C6CS00135A http://doi.org/10.1039/C6CS00135A .

Das, S.; Heasman, P.; Ben, T.; Qiu, S. . 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 .

Lugger, J.; Mulder, D. J.; Sijbesma, R.; Schenning, A. . Nanoporous polymers based on liquid crystals . Materials (Basel) , 2018 . 11 104 - 121 . DOI: 10.3390/ma11010104 http://doi.org/10.3390/ma11010104 .

Gopinadhan, M.; Deshmukh, P.; Choo, Y.; Majewski, P. W.; Bakajin, O.; Elimelech, M.; Kasi, R. M.; Osuji, C. O. . Thermally switchable aligned nanopores by magnetic-field directed self-assembly of block copolymers . Adv. Mater. , 2014 . 26 5148 - 5154 . DOI: 10.1002/adma.201401569 http://doi.org/10.1002/adma.201401569 .

Deshmukh, P.; Gopinadhan, M.; Choo, Y.; Ahn, S.; Majewski, P. W.; Yoon, S. Y.; Bakajin, O.; Elimelech, M.; Osuji, C. O.; Kasi, R. M. . Molecular design of liquid crystalline brush-like block copolymers for magnetic field directed self-assembly: a platform for functional materials . ACS Macro Lett. , 2014 . 3 462 - 466 . DOI: 10.1021/mz500161k http://doi.org/10.1021/mz500161k .

Yin, J.; Yao, X. P.; Liou, J. Y.; Sun, W.; Sun, Y. S.; Wang, Y. . Membranes with highly ordered straight nanopores by selective swelling of fast perpendicularly aligned block copolymers . ACS Nano , 2013 . 7 9961 - 9974 . DOI: 10.1021/nn403847z http://doi.org/10.1021/nn403847z .

Sun, W.; Wang, Z. G.; Yao, X. P.; Guo, L. M.; Chen, X. Q.; Wang, Y. . Surface-active isoporous membranes nondestructively derived from perpendicularly aligned block copolymers for size-selective separation . J. Membr. Sci. , 2014 . 466 229 - 237 . DOI: 10.1016/j.memsci.2014.04.055 http://doi.org/10.1016/j.memsci.2014.04.055 .

Wu, D. C.; Xu, F.; Sun, B.; Fu, R. W.; He, H. K.; Matyjaszewski, K. . Design and preparation of porous polymers . Chem. Rev. , 2012 . 112 3959 - 4015 . DOI: 10.1021/cr200440z http://doi.org/10.1021/cr200440z .

Nickmans, K.; Schenning, A. P. H. J. . Directed self-assembly of liquid-crystalline molecular building blocks for sub-5 nm nanopatterning . Adv. Mater. , 2018 . 30 1703713 DOI: 10.1002/adma.201703713 http://doi.org/10.1002/adma.201703713 .

Gin, D. L.; Noble, R. D. . Designing the next generation of chemical separation membranes . Science , 2011 . 332 674 - 676 . DOI: 10.1126/science.1203771 http://doi.org/10.1126/science.1203771 .

Lyu, X. L.; Pan, H. B.; Shen, Z. H.; Fan, X. H. . Self-assembly and properties of block copolymers containing mesogen-jacketed liquid crystalline polymers as rod blocks . Chinese J. Polym. Sci. , 2018 . 36 811 - 821 . DOI: 10.1007/s10118-018-2115-x http://doi.org/10.1007/s10118-018-2115-x .

Lee, H. K.; Lee, H.; Ko, Y. H.; Chang, Y. J.; Oh, N. K.; Zin, W. C.; Kim, K. . Synthesis of a nanoporous polymer with hexagonal channels from supramolecular discotic liquid crystals . Angew. Chem. Int. Ed. , 2001 . 40 2669 - 2671 . DOI: 10.1002/1521-3773(20010716)40:14<2669::AID-ANIE2669>3.0.CO;2-Q http://doi.org/10.1002/1521-3773(20010716)40:14<2669::AID-ANIE2669>3.0.CO;2-Q .

Werber, J. R.; Osuji, C. O.; Elimelech, M. . Materials for next-generation desalination and water purification membranes . Nat. Rev. Mater. , 2016 . 1 16018 DOI: 10.1038/natrevmats.2016.18 http://doi.org/10.1038/natrevmats.2016.18 .

Wöhrle, T.; Wurzbach, I.; Kirres, J.; Kostidou, A.; Kapernaum, N.; Litterscheidt, J.; Haenle, J. C.; Staffeld, P.; Baro, A.; Giesselmann, F.; Laschat, S. . Discotic liquid crystals . Chem. Rev. , 2016 . 116 1139 - 1241 . DOI: 10.1021/acs.chemrev.5b00190 http://doi.org/10.1021/acs.chemrev.5b00190 .

Broer, D. J.; Bastiaansen, C. M. W.; Debije, M. G.; Schenning, A. P. H. J. . Functional organic materials based on polymerized liquid-crystal monomers: supramolecular hydrogen-bonded systems . Angew. Chem. Int. Ed. , 2012 . 51 7102 - 7109 . DOI: 10.1002/anie.201200883 http://doi.org/10.1002/anie.201200883 .

Concellón, A.; Schenning, A. P. H. J.; Romero, P.; Marcos, M.; Serrano, J. L. . Size-selective adsorption in nanoporous polymers from coumarin photo-cross-linked columnar liquid crystals . Macromolecules , 2018 . 51 2349 - 2358 . DOI: 10.1021/acs.macromol.8b00067 http://doi.org/10.1021/acs.macromol.8b00067 .

Bogels, G. M.; Lugger, J. A. M.; Goor, O. J. G. M.; Sijbesma, R. P. . Size-selective binding of sodium and potassium ions in nanoporous thin films of polymerized liquid crystals . Adv. Funct. Mater. , 2016 . 26 8023 - 8030 . DOI: 10.1002/adfm.201603408 http://doi.org/10.1002/adfm.201603408 .

Bhattacharjee, S.; Lugger, J. A. M.; Sijbesma, R. P. . Tailoring pore size and chemical interior of near 1 nm sized pores in a nanoporous polymer based on a discotic liquid crystal . Macromolecules , 2017 . 50 2777 - 2783 . DOI: 10.1021/acs.macromol.7b00013 http://doi.org/10.1021/acs.macromol.7b00013 .

Sakamoto, T.; Ogawa, T.; Nada, H.; Nakatsuji, K.; Mitani, M.; Soberats, B.; Kawata, K.; Yoshio, M.; Tomioka, H.; Sasaki, T.; Kimura, M.; Henmi, M.; Kato, T. . Development of nanostructured water treatment membranes based on thermotropic liquid crystals: molecular design of sub-nanoporous materials . Adv. Sci. , 2018 . 5 1700405 DOI: 10.1002/advs.201700405 http://doi.org/10.1002/advs.201700405 .

Marets, N.; Kuo, D.; Torrey, J. R.; Sakamoto, T.; Henmi, M.; Katayama, H.; Kato, T. . Highly efficient virus rejection with self-organized membranes based on a crosslinked bicontinuous cubic liquid crystal . Adv. Healthc. Mater. , 2017 . 6 1700252 DOI: 10.1002/adhm.201700252 http://doi.org/10.1002/adhm.201700252 .

Feng, X. D.; Tousley, M. E.; Cowan, M. G.; Wiesenauer, B. R.; Nejati, S.; Choo, Y.; Noble, R. D.; Elimelech, M.; Gin, D. L.; Osuji, C. O. . Scalable fabrication of polymer membranes with vertically aligned 1 nm pores by magnetic field directed self-assembly . ACS Nano , 2014 . 8 11977 - 11986 . DOI: 10.1021/nn505037b http://doi.org/10.1021/nn505037b .

Feng, X. D.; Nejati, S.; Cowan, M. G.; Tousley, M. E.; Wiesenauer, B. R.; Noble, R. D.; Elimelech, M.; Gin, D. L.; Osuji, C. O. . Thin polymer films with continuous vertically aligned 1 nm pores fabricated by soft confinement . ACS Nano , 2016 . 10 150 - 158 . DOI: 10.1021/acsnano.5b06130 http://doi.org/10.1021/acsnano.5b06130 .

Li, C.; Cho, J.; Yamada, K.; Hashizume, D.; Araoka, F.; Takezoe, H.; Aida, T.; Ishida, Y. . Macroscopic ordering of helical pores for arraying guest molecules noncentrosymmetrically . Nat. Commun. , 2015 . 6 8418 - 8427 . DOI: 10.1038/ncomms9418 http://doi.org/10.1038/ncomms9418 .

Miyajima, D.; Araoka, F.; Takezoe, H.; Kim, J.; Kato, K.; Takata, M.; Aida, T. . Ferroelectric columnar liquid crystal featuring confined polar groups within core-shell architecture . Science , 2012 . 336 209 - 213 . DOI: 10.1126/science.1217954 http://doi.org/10.1126/science.1217954 .

Kato, T.; Yoshio, M.; Ichikawa, T.; Soberats, B.; Ohno, H.; Funahashi, M. . Transport of ions and electrons in nanostructured liquid crystals . Nat. Rev. Mater. , 2017 . 2 17001 DOI: 10.1038/natrevmats.2017.1 http://doi.org/10.1038/natrevmats.2017.1 .

Nickmans, K.; Bogels, G. M.; Sanchez-Somolinos, C.; Murphy, J. N.; Leclere, P.; Voets, I. K.; Schenning, A. P. H. J. . 3D orientational control in self-assembled thin films with sub-5 nm features by light . Small , 2017 . 13 1701043 DOI: 10.1002/smll.201701043 http://doi.org/10.1002/smll.201701043 .

Kwon, K.; Park, K.; Jung, H. T. . Long-range single domain array of a 5 nm pattern of supramolecules via solvent annealing in a double-sandwich cell . Nanoscale , 2018 . 10 8459 - 8470 . DOI: 10.1039/C8NR01291A http://doi.org/10.1039/C8NR01291A .

Kwon, K.; Ok, J. M.; Kim, Y. H.; Kim, J. S.; Jung, W. B.; Cho, S. Y.; Jung, H. T. . Direct observation of highly ordered dendrimer soft building blocks over a large area . Nano Lett. , 2015 . 15 7552 - 7557 . DOI: 10.1021/acs.nanolett.5b03284 http://doi.org/10.1021/acs.nanolett.5b03284 .

Yoshio, M.; Kagata, T.; Hoshino, K.; Mukai, T.; Ohno, H.; Kato, T. . One-dimensional ion-conductive polymer films: alignment and fixation of ionic channels formed by self-organization of polymerizable columnar liquid crystals . J. Am. Chem. Soc. , 2006 . 128 5570 - 5577 . DOI: 10.1021/ja0606935 http://doi.org/10.1021/ja0606935 .

Lugger, J. A. M.; Mulder, D. J.; Bhattacharjee, S.; Sijbesma, R. P. . Homeotropic self-alignment of discotic liquid crystals for nanoporous polymer films . ACS Nano , 2018 . 12 6714 - 6724 . DOI: 10.1021/acsnano.8b01822 http://doi.org/10.1021/acsnano.8b01822 .

Feng, X. D.; Kawabata, K.; Kaufman, G.; Elimelech, M.; Osuji, C. O. . Highly selective vertically aligned nanopores in sustainably derived polymer membranes by molecular templating . ACS Nano , 2017 . 11 3911 - 3921 . DOI: 10.1021/acsnano.7b00304 http://doi.org/10.1021/acsnano.7b00304 .

Xiong, J. F.; Luo, S. H.; Huo, J. P.; Liu, J. Y.; Chen, S. X.; Wang, Z. Y. . Design, synthesis, and characterization of 1,3,5-tri(1 H -benzo[ d ]imidazol-2-yl)benzene-based fluorescent supramolecular columnar liquid crystals with a broad mesomorphic range . J. Org. Chem. , 2014 . 79 8366 - 8373 . DOI: 10.1021/jo5016954 http://doi.org/10.1021/jo5016954 .

Biedermann, F.; Schneider, H. . Experimental binding energies in supramolecular complexes . Chem. Rev. , 2016 . 116 5216 - 5300 . DOI: 10.1021/acs.chemrev.5b00583 http://doi.org/10.1021/acs.chemrev.5b00583 .

Beginn, U. . Thermotropic columnar mesophases from N–H···O, and N···H–O hydrogen bond supramolecular mesogenes . Prog. Polym. Sci. , 2003 . 28 1049 - 1105 . DOI: 10.1016/S0079-6700(02)00150-8 http://doi.org/10.1016/S0079-6700(02)00150-8 .

Bogels, G. M.; van Kuringen, H. P. C.; Shishmanova, I. K.; Voets, I. K.; Schenning, A. P. H. J.; Sijbesma, R. P. . Selective absorption of hydrophobic cations in nanostructured porous materials from crosslinked hydrogen-bonded columnar liquid crystals . Adv. Mater. Interfaces , 2015 . 2 1500022 DOI: 10.1002/admi.201500022 http://doi.org/10.1002/admi.201500022 .

Pisula, W.; Kastler, M.; El Hamaoui, B.; Garcia-Gutierrez, M. C.; Davies, R. J.; Riekel, C.; Mullen, K. . Dendritic morphology in homeotropically aligned discotic films . ChemPhysChem , 2007 . 8 1025 - 1028 . DOI: 10.1002/cphc.200600787 http://doi.org/10.1002/cphc.200600787 .

Pisula, W.; Tomović, Ž.; El Hamaoui, B.; Watson, M. D.; Pakula, T.; Müllen, K. . Control of the homeotropic order of discotic hexa-peri-hexabenzocoronenes . Adv. Funct. Mater. , 2005 . 15 893 - 904 . DOI: 10.1002/adfm.200400391 http://doi.org/10.1002/adfm.200400391 .

Zhuang, Y.; Yu, F.; Chen, J.; Ma, J. . Batch and column adsorption of methylene blue by graphene/alginate nanocomposite: comparison of single-network and double-network hydrogels . J. Environ. Chem. Eng. , 2016 . 4 147 - 156 . DOI: 10.1016/j.jece.2015.11.014 http://doi.org/10.1016/j.jece.2015.11.014 .

Li, Y.; Du, Q.; Liu, T.; Sun, J.; Wang, Y.; Wu, S.; Wang, Z.; Xia, Y.; Xia, L. . Methylene blue adsorption on graphene oxide/calcium alginate composites . Carbohydr. Polym. , 2013 . 95 501 - 507 . DOI: 10.1016/j.carbpol.2013.01.094 http://doi.org/10.1016/j.carbpol.2013.01.094 .

Wang, G.; Garvey, C. J.; Zhao, H.; Huang, K.; Kong, L. . Toward the fabrication of advanced nanofiltration membranes by controlling morphologies and mesochannel orientations of hexagonal lyotropic liquid crystals . Membranes (Basel) , 2017 . 7 37 - 57 . DOI: 10.3390/membranes7030037 http://doi.org/10.3390/membranes7030037 .

Stevens, D. M.; Shu, J. Y.; Reichert, M.; Roy, A. . Next-generation nanoporous materials: progress and prospects for reverse osmosis and nanofiltration . Ind. Eng. Chem. Res. , 2017 . 56 10526 - 10551 . DOI: 10.1021/acs.iecr.7b02411 http://doi.org/10.1021/acs.iecr.7b02411 .

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Effects of Side Chains with Similar Lengths and Different Structures of Polyimides on Liquid Crystal Alignment Behavior

Squaramide-directed Cooperative One-dimensional Assembly in Telechelic Polydimethylsiloxane for Hierarchical Network Formation

Regulation of Microphase Separation in Bio-based Thermoplastic Polyurethanes Driven by Hard Segment Content

Hydrogen Bonding in Gel Polymer Electrolyte Enables High Performance High-mass-loading Silicon Anode

Anti-biofouling Hydrogels: Surface Hydration, Classification, and Biomedical Applications