Abstract
The development of new proton-conducting materials through a convenient and low-cost method is crucial in fuel cell technology. Supramolecular hydrogen-bonded organic networks (SHONs) are constructed by self-assembly of multi-component organic molecules through hydrogen bond interactions, in which the intermolecular hydrogen bond bridge constructed by Brønsted acid–base pairs and water molecules can accelerate the process of protonation and deprotonation for efficient proton conduction. The particle state and hydrophilicity of SHONs directly affect the grain boundary conductivity and the stability of the hydrogen bond network, which play a decisive role in the proton conduction. In this study, cellulose fibers were used as carrier to induce the in-situ growth of SHONs, constructed by melamine and 1,2-ethanedisulfonic acid, to prepare composite paper for a promising proton exchange membrane. Cellulose fibers exhibited significant regulation on the particle state and hydrophilicity of SHONs. Scanning electron microscopy and surface area analysis showed that the introduction of cellulose fiber changed the particle state of SHONs. Compared with pure SHONs, SHONs grown in-situ on cellulose fibers exhibited a smaller particle size and a more continuous arrangement, which was beneficial to improve the grain boundary conductivity. Contact angle measurements proved that the introduction of cellulose fibers improved the hydrophilicity of SHONs. This contributed to improving the stability of the hydrogen bond networks and the smoothness of the proton conduction channel. The regulation effect of cellulose fibers on SHONs improved the proton conduction efficiency of SHONs. The formed composite paper with SHONs grown in-situ on cellulose fibers exhibited a proton conduction value of up to 6.46 × 10–2 S cm−1 at 75 °C and 85% RH. This work provides a novel strategy for preparing highly efficient proton conducting composite paper for potential application in proton-exchange membrane fuel cells.
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References
Artz J, Palkovits R (2018) Cellulose-based platform chemical: the path to application. Curr Opin Green Sust 14:14–18. https://doi.org/10.1016/j.cogsc.2018.05.005
Bayer T, Cunning BV, Selyanchyn R, Nishihara M, Fujikawa S, Sasaki K, Lyth SM (2016) High temperature proton conduction in nanocellulose membranes: paper fuel cells. Chem Mater 28(13):4805–4814. https://doi.org/10.1021/acs.chemmater.6b01990
Chand S, Pal SC, Pal A, Ye Y, Lin Q, Zhang Z, Xiang S, Das MC (2019) Metalo hydrogen-bonded organic frameworks (MHOFs) as new class of crystalline materials for protonic conduction. Chem Eur J 25(7):1691–1695. https://doi.org/10.1002/chem.201805177
Chen Y, Chelgani SC, Bu X, Xie G (2021) Effect of the ultrasonic standing wave frequency on the attractive mineralization for fine coal particle flotation. Ultrason Sonochem 77:105682. https://doi.org/10.1016/j.ultsonch.2021.105682
Chithambharan A, Pottail L, Sharma SC, Kumaraswamy BE (2021) FT-IR fingerprinting as an Analytical tool for determination of Melamine leaching from Melamine tablewares and their Biological implications. J Food Sci Technol 58(3):855–861. https://doi.org/10.1007/s13197-020-04599-9
Chu ZT, Li RY, Zhou CC, Liu HT, Lu J, Wang SN, Li YW (2021) Two acidic coordination polymers containing uncoordinated carboxyl groups: syntheses, crystal structures and proton conductivities in Nafion composite membranes. J Solid State Chem 295:121932. https://doi.org/10.1016/j.jssc.2020.121932
Dang X, Chen H, Shan Z, Zhen W, Yang M (2018) The oxidation of potato starch by electro-Fenton system in the presence of Fe(II) ions. Int J Biol Macromol 121:113–119. https://doi.org/10.1016/j.ijbiomac.2018.10.012
Daud WRW, Rosli RE, Majlan EH, Hamid SAA, Mohamed R, Husaini T (2017) PEM fuel cell system control: A review. Renew Energ 113:620–638. https://doi.org/10.1016/j.renene.2017.06.027
Dong XY, Wang JH, Liu SS, Han Z, Tang QJ, Li FF, Zang SQ (2018) Synergy between Isomorphous Acid and Basic Metal-Organic Frameworks for Anhydrous Proton Conduction of low-cost hybrid membranes at high temperatures. ACS Appl Mater Inter 10(44):38209–38216. https://doi.org/10.1021/acsami.8b12846
Escorihuela J, Narducci R, Compañ V, Costantino F (2019) Proton conductivity of composite polyelectrolyte membranes with metal-organic frameworks for fuel cell applications. Adv Mater Interfaces 6(2):1801146. https://doi.org/10.1002/admi.201801146
Hu F, Liu C, Wu M, Pang J, Jiang F, Yuan D, Hong M (2017) An ultrastable and easily regenerated hydrogen-bonded organic molecular framework with permanent porosity. Angew Chem Int Ed 56(8):2101–2104. https://doi.org/10.1002/anie.201610901
Ji NN, Shi ZQ, Xie XX, Li G (2020) Polyoxometalate-based hydrogen-bonded organic frameworks as a new class of proton conducting materials. CrystEngComm 22(47):8161–8165. https://doi.org/10.1039/D0CE01578D
Jiang GP, Zhang J, Qiao JL, Jiang YM, Zarrin H, Chen Z, Hong F (2015) Bacterial nanocellulose/Nafion composite membranes for low temperature polymer electrolyte fuel cells. J Power Sources 273:697–706. https://doi.org/10.1016/j.jpowsour.2014.09.145
Karim MR, Hatakeyama K, Koinuma M, Hayami S (2017) Proton conductors produced by chemical modifications of carbon allotropes, perovskites and metal organic frameworks. J Mater Chem A 5(16):7243–7256. https://doi.org/10.1039/C6TA10923C
Kusoglu A, Weber AZ (2017) New insights into perfluorinated sulfonic-acid ionomers. Chem Rev 117(3):987–1104. https://doi.org/10.1021/acs.chemrev.6b00159
Lee CM, Kubicki JD, Fan B, Zhong L, Jarvis MC, Kim SH (2015) Hydrogen-bonding network and OH stretch vibration of cellulose: comparison of computational modeling with polarized IR and SFG spectra. J Phys Chem B 119(49):15138–15149. https://doi.org/10.1021/acs.jpcb.5b08015
Liu M, Chen L, Lewis S, Chong SY, Little MA, Hasell T, Aldous IM, Brown CM, Smith MW, Morrison CA, Hardwick LJ, Cooper AI (2016) Three-dimensional protonic conductivity in porous organic cage solids. Nat Commun 7(1):1–9. https://doi.org/10.1038/ncomms12750
Lü J, Cao R (2016) Porous organic molecular frameworks with extrinsic porosity: a platform for carbon storage and separation. Angew Chem Int Ed 55(33):9474–9480. https://doi.org/10.1002/anie.201602116
Pal SC, Mukherjee D, Sahoo R, Mondal S, Das MC (2021) Proton-conducting hydrogen-bonded organic frameworks. ACS Energy Lett 6:4431–4453. https://doi.org/10.1021/acsenergylett.1c02045
Saedi S, Garcia CV, Kim JT, Shin GH (2021) Physical and chemical modifications of cellulose fibers for food packaging applications. Cellulose 28(14):8877–8897. https://doi.org/10.1007/s10570-021-04086-0
Shi ZQ, Ji NN, Guo KM, Li G (2020) Crystalline hydrogen-bonded supramolecular frameworks (HSFs) as new class of proton conductive materials. Appl Surf Sci 504:144484. https://doi.org/10.1016/j.apsusc.2019.144484
Shin DW, Guiver MD, Lee YM (2017) Hydrocarbon-based polymer electrolyte membranes: importance of morphology on ion transport and membrane stability. Chem Rev 117(6):4759–4805. https://doi.org/10.1021/acs.chemrev.6b00586
Singh B, Ghosh S, Aich S, Roy B (2017) Low temperature solid oxide electrolytes (LT-SOE): a review. J Power Sources 339:103–135. https://doi.org/10.1016/j.jpowsour.2016.11.019
Smolarkiewicz I, Rachocki A, Pogorzelec-Glaser K, Pankiewicz R, Ławniczak P, Łapiński A, Jarek M, Tritt-Goc J (2015) Proton-conducting microcrystalline cellulose doped with imidazole Thermal and Electrical Properties. Electrochim Acta 155:38–44. https://doi.org/10.1016/j.electacta.2014.11.205
Sun B, Hou Q, Liu Z, Ni Y (2015) Sodium periodate oxidation of cellulose nanocrystal and its application as a paper wet strength additive. Cellulose 22(2):1135–1146. https://doi.org/10.1007/s10570-015-0575-5
Sun M, Zhai LF, Li WW, Yu HQ (2016) Harvest and utilization of chemical energy in wastes by microbial fuel cells. Chem Soc Rev 45(10):2847–2870. https://doi.org/10.1039/C5CS00903K
Vanderfleet OM, Cranston ED (2021) Production routes to tailor the performance of cellulose nanocrystals. Nat Rev Mater 6(2):124–144. https://doi.org/10.1038/s41578-020-00239-y
Wang S, Lu A, Zhang L (2016) Recent advances in regenerated cellulose materials. Prog Polym Sci 53:169–206. https://doi.org/10.1016/j.progpolymsci.2015.07.003
Wang S, Wahiduzzaman M, Davis L, Tissot A, Shepard W, Marrot J, Martineau-Corcos C, Hamdane D, Maurin G, Devautous-Vinot S, Serre C (2018) A robust zirconium amino acid metal-organic framework for proton conduction. Nat Commun 9(1):1–8. https://doi.org/10.1038/s41467-018-07414-4
Wang L, Deng N, Wang G, Ju J, Cheng B, Kang W (2019) Constructing amino-functionalized flower-like metal–organic framework nanofibers in sulfonated poly (ether sulfone) proton exchange membrane for simultaneously enhancing interface compatibility and proton conduction. ACS Appl Mater Inter 11(43):39979–39990. https://doi.org/10.1021/acsami.9b13496
Wang Y, Zhang M, Yang Q, Yin J, Liu D, Shang Y, Kang Z, Wang R, Sun D, Jiang J (2020) Single-crystal-to-single-crystal transformation and proton conductivity of three hydrogen-bonded organic frameworks. Chem Comm 56(99):15529–15532. https://doi.org/10.1039/D0CC05402J
Wang Y, Yin J, Liu D, Gao C, Kang Z, Wang R, Sun D, Jiang J (2021) Guest-tuned proton conductivity of a porphyrinylphosphonate-based hydrogen-bonded organic framework. J Mater Chem A 9(5):2683–2688. https://doi.org/10.1039/D0TA07207A
Wei MJ, Gao Y, Li K, Li B, Fu JQ, Zang HY, Shao KZ, Su ZM (2019) Supramolecular hydrogen-bonded organic networks through acid–base pairs as efficient proton-conducting electrolytes. CrystEngComm 21(33):4996–5001. https://doi.org/10.1039/C9CE00762H
Widelicka M, Pogorzelec-Glaser K, Pietraszko A, Ławniczak P, Pankiewicz R, Łapiński A (2017) Order–disorder phase transition in an anhydrous pyrazole-based proton conductor: the enhancement of electrical transport properties. Phys Chem Chem Phys 19(37):25653–25661. https://doi.org/10.1039/C7CP05708C
Xi Y, Li DS, Newbloom GM, Tatum WK, O’Donnell M, Luscombe CK, Pozzo LD (2018) Sonocrystallization of conjugated polymers with ultrasound fields. Soft Matter 14(24):4963–4976. https://doi.org/10.1039/C8SM00905H
Xie X, Zhang Z, Zhang J, Hou L, Li Z, Li G (2019) Impressive proton conductivities of two highly stable metal–organic frameworks constructed by substituted imidazoledicarboxylates. Inorg Chem 58(8):5173–5182. https://doi.org/10.1021/acs.inorgchem.9b00274
Xing G, Yan T, Das S, Ben T, Qiu S (2018) Synthesis of crystalline porous organic salts with high proton conductivity. Angew Chem Int Ed 57(19):5345–5349. https://doi.org/10.1002/anie.201800423
Xu XQ, Cao LH, Yang Y, Zhao F, Bai XT, Zang SQ (2021) Hybrid nafion membranes of ionic hydrogen-bonded organic framework materials for proton conduction and PEMFC applications. ACS Appl Mater Inter 13(47):56566–56574. https://doi.org/10.1021/acsami.1c15748
Yan GY, Qian ZJ, Rouhani F, Kaviani H, Hashemi L, Bigdeli F, Gao XM, Qiao LP, Liu KG, Morsali A, Liu T (2021) Engineered design of a new HOF by simultaneous monitoring of reaction environment conductivity. J Solid State Chem 307:122834. https://doi.org/10.1016/j.jssc.2021.122834
Yang D, Kumar V (2012) Preparation and characterization of novel oxidized cellulose acetate methyl esters. Carbohydr Polym 90(4):1486–1493. https://doi.org/10.1016/j.carbpol.2012.07.019
Yang Q, Wang Y, Shang Y, Du J, Yin J, Liu D, Kang Z, Wang R, Sun D, Jiang J (2020) Three hydrogen-bonded organic frameworks with water-induced Single-Crystal-to-Single-Crystal transformation and high proton conductivity. Cryst Growth Des 20(5):3456–3465. https://doi.org/10.1021/acs.cgd.0c00235
Yang Y, Zhang P, Hao L, Cheng P, Chen Y, Zhang Z (2021) Grotthuss proton-conductive covalent organic frameworks for efficient proton pseudocapacitors. Angew Chem 133(40):22009–22016. https://doi.org/10.1002/ange.202105725
Ye Y, Gong L, Xiang S, Zhang Z, Chen B (2020) Metal–organic frameworks as a versatile platform for proton conductors. Adv Mater 32(21):1907090. https://doi.org/10.1002/adma.201907090
Yue L, Xie Y, Zheng Y, He W, Guo S, Sun Y, Zhang T, Liu S (2017) Sulfonated bacterial cellulose/polyaniline composite membrane for use as gel polymer electrolyte. Compos Sci Technol 145:122–131. https://doi.org/10.1016/j.compscitech.2017.04.002
Zhang C, Mo J, Fu Q, Liu Y, Wang S, Nie S (2021) Wood-cellulose-fiber-based functional materials for triboelectric nanogenerators. Nano Energy 81:105637. https://doi.org/10.1016/j.nanoen.2020.105637
Zhu W, Liu L, Liao Q, Chen X, Qian Z, Shen J, Liang J, Yao J (2016) Functionalization of cellulose with hyperbranched polyethylenimine for selective dye adsorption and separation. Cellulose 23(6):3785–3797. https://doi.org/10.1007/s10570-016-1045-4
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This work was financially supported by the National Natural Science Foundation of China (Grant No. 22108029), the Fundamental Research Funds for the Central Universities (2572019BB01), and the Young Elite Scientists Sponsorship Program by CAST (2018QNRC001).
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Li, X., Xiang, Y., Huang, X. et al. Supramolecular hydrogen-bonded organic networks grown on cellulose fibers for efficient proton conduction. Cellulose 29, 6247–6259 (2022). https://doi.org/10.1007/s10570-022-04658-8
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DOI: https://doi.org/10.1007/s10570-022-04658-8