Citation: Lu Chen, Kuan Hu, Si-Ting Sun, Hai Jiang, Dong Huang, Kun-Yu Zhang, Li Pan, Yue-Sheng Li. Toughening Poly(lactic acid) with Imidazolium-based Elastomeric Ionomers[J]. Chinese Journal of Polymer Science, ;2018, 36(12): 1342-1352. doi: 10.1007/s10118-018-2143-6 shu

Toughening Poly(lactic acid) with Imidazolium-based Elastomeric Ionomers

Lu Chen ¹ ,
Kuan Hu ¹ ,
Si-Ting Sun ² ,
Hai Jiang ² ,
Dong Huang ² ,
Kun-Yu Zhang ^2,, ,
Li Pan ¹ ,
Yue-Sheng Li ^1,3,,

a.
Tianjin Key Laboratory of Composite and Functional Materials, School of Materials Science and Engineering, Tianjin University, Tianjin 300350, China
b.
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
c.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China

Corresponding author: Kun-Yu Zhang, kyzhang@tju.edu.cn (K.Y.Z.) Yue-Sheng Li, ysli@tju.edu.cn (Y.S.L.)
Received Date: 27 March 2018
Revised Date: 11 April 2018
Accepted Date: 17 April 2018
Available Online: 11 May 2018

Imidazolium-based elastomeric ionomers (i-BIIR) were facilely synthesized by ionically modified brominated poly(isobutylene-co-isoprene) (BIIR) with different alkyl chain imidazole and thoroughly explored as novel toughening agents for poly(lactic acid) (PLA). The miscibility, thermal behavior, phase morphology and mechanical property of ionomers and blends were investigated through dynamic mechanical analyses (DMA), differential scanning calorimetry (DSC), scanning electron microscopy (SEM), tensile and impact testing. DMA and SEM results showed that better compatibility between the PLA and i-BIIR was achieved compared to the PLA/unmodified BIIR elastomer. A remarkable improvement in ductility with an optimum elongation at break up to 235% was achieved for the PLA/i-BIIR blends with 1-dodecylimidazole alkyl chain (i-BIIR-12), more than 10 times higher than that of pure PLA. The impact strengths of PLA were enhanced from 1.9 kJ/m² to 4.1 kJ/m² for the PLA/10 wt% i-BIIR-12 blend. Toughening mechanism had been established by systematical analysis of the compatibility, intermolecular interaction and phase structures of the blends. Interfacial cavitations initiated massive shear yielding of the PLA matrix owing to a suitable interfacial adhesion which played a key role in the enormous toughening effect in these blends. We believed that introducing imidazolium group into the BIIR elastomer was vital for the formation of a suitable interfacial adhesion.
- Imidazolium-based ionomer,
- Poly(lactic acid),
- Brominated poly(isobutylene-co-isoprene),
- Toughening,
- Blend
1. [1]
  Chen, G. Q.; Patel, M. K. Plastics derived from biological sources: present and future: a technical and environmental review. Chem. Rev. 2012, 112(4), 2082−2099 doi: 10.1021/cr200162d
2. [2]
  Zhang, X. Y.; Fevre, M.; Jones, G. O.; Waymouth, R. M. Catalysis as an enabling science for sustainable polymers. Chem. Rev. 2018, 118(2), 839−885 doi: 10.1021/acs.chemrev.7b00329
3. [3]
  Auras, R.; Harte, B.; Selke, S. An overview of polylactides as packaging materials. Macromol. Biosci. 2004, 4(9), 835−864 doi: 10.1002/(ISSN)1616-5195
4. [4]
  Farah, S.; Anderson, D. G.; Langer, R. Physical and mechanical properties of PLA, and their functions in widespread applications - a comprehensive review. Adv. Drug Deliv. Rev. 2016, 107(21), 367−392
5. [5]
  Hou, J. Z.; Sun, X. P.; Zhang, W. X.; Li, L. L.; Teng, H. Preparation and characterization of electrospun fibers based on poly(L-lactic acid)/cellulose acetate. Chinese J. Polym. Sci. 2012, 30(6), 916−922 doi: 10.1007/s10118-012-1191-6
6. [6]
  Yao, C.; Li, X. S.; Neoh, K. G.; Shi, Z. L.; Kang, E. T. Antibacterial poly(D,L-lactide) (PDLLA) fibrous membranes modified with quaternary ammonium moieties. Chinese J. Polym. Sci. 2010, 28(4), 581−588 doi: 10.1007/s10118-010-9094-x
7. [7]
  Wu, N. J.; Zhang, H.; Fu, G. L. Super-tough poly(lactide) thermoplastic vulcanizates based on modified natural rubber. ACS Sustain. Chem. Eng. 2017, 5(1), 78−84 doi: 10.1021/acssuschemeng.6b02197
8. [8]
  Wang, P.; Xu, P.; Wei, H. B.; Fang, H. G.; Ding, Y. S. Effect of block copolymer containing ionic liquid moiety on interfacial polarization in PLA/PCL blends. J. Appl. Polym. Sci. 2018, 10.1002/APP.46161 doi: 10.1002/APP.46161
9. [9]
  Delgado, P. A.; Hillmyer, M. A. Combining block copolymers and hydrogen bonding for poly(lactide) toughening. RSC Adv. 2014, 4(26), 13266−13273 doi: 10.1039/c4ra00150h
10. [10]
  Hao, Y. P.; Ge, H. H.; Han, L. J.; Zhang, H. L.; Dong, L. S.; Sun, S. L. Thermal and mechanical properties of polylactide toughened with a butyl acrylate-ethyl acrylate-glysidyl methacrylate copolymer. Chinese J. Polym. Sci. 2013, 31(11), 1519−1527 doi: 10.1007/s10118-013-1350-4
11. [11]
  Zhang, K. Toughened sustainable green composites from poly(3-hydroxybutyrate-co-3-hydroxyvalerate) based ternary blends and miscanthus biofiber. ACS Sustain. Chem. Eng. 2014, 2(10), 2345−2354 doi: 10.1021/sc500353v
12. [12]
  Yu, R. L.; Zhang, L. S.; Feng, Y. H.; Zhang, R. Y.; Zhu, J. Improvement in toughness of polylactide by melt blending with bio-based poly(ester)urethane. Chinese J. Polym. Sci. 2014, 32(8), 1099−1110 doi: 10.1007/s10118-014-1487-9
13. [13]
  Xing, Q.; Li, R. B.; Dong, X.; Zhang, X. Q.; Zhang, L. Y.; Wang, D. J. Phase morphology, crystallization behavior and mechanical properties of poly(L-lactide) toughened with biodegradable polyurethane: effect of composition and hard segment ratio. Chinese J. Polym. Sci. 2015, 33(9), 1294−1304 doi: 10.1007/s10118-015-1679-y
14. [14]
  Zhang, K. Y.; Ran, X. H.; Wang, X. M.; Han, C. Y.; Han, L. J.; Wen, X.; Zhuang, Y. G.; Dong, L. S. Improvement in toughness and crystallization of poly(L-lactic acid) by melt blending with poly(epichlorohydrin-co-ethylene oxide). Polym. Eng. Sci. 2011, 51(12), 2370−2380 doi: 10.1002/pen.v51.12
15. [15]
  Yuan, D. S.; Chen, Z. H.; Xu, C. H.; Chen, K. L.; Chen, Y. K. Fully biobased shape memory material based on novel cocontinuous structure in poly(lactic acid)/natural rubber TPVs fabricated via peroxide-induced dynamic vulcanization and in situ interfacial compatibilization. ACS Sustain. Chem. Eng. 2015, 3(11), 2856−2865 doi: 10.1021/acssuschemeng.5b00788
16. [16]
  Zhang, K. Y.; Nagarajan, V.; Misra, M.; Mohanty, A. K. Supertoughened renewable PLA reactive multiphase blends system: phase morphology and performance. ACS Appl. Mater. Interfaces 2014, 6(15), 12436−12448 doi: 10.1021/am502337u
17. [17]
  Dong, W. Y.; He, M. F.; Wang, H. T.; Ren, F. L.; Zhang, J. Q.; Zhao, X. W.; Li, Y. J. PLLA/ABS blends compatibilized by reactive comb polymers: double T_g depression and significantly improved toughness. ACS Sustain. Chem. Eng. 2015, 3(10), 2542−2550 doi: 10.1021/acssuschemeng.5b00740
18. [18]
  Lin, Y.; Zhang, K. Y.; Dong, Z. M.; Dong, L. S.; Li, Y. S. Study of hydrogen-bonded blend of polylactide with biodegradable hyperbranched poly(ester amide). Macromolecules 2007, 40(17), 6257−6267 doi: 10.1021/ma070989a
19. [19]
  Han, S. I.; Yoo, Y. T; Kim, D. K.; Im, S. S. Biodegradable aliphatic polyester ionomers. Macromol. Biosci. 2004, 4(3), 199−207 doi: 10.1002/(ISSN)1616-5195
20. [20]
  Park, S. B.; Hwang, S. Y.; Moon, C. W.; Im, S. S. Plasticizer effect of novel PBS ionomer in PLA/PBS ionomer blends. Macromol. Res. 2010, 18(5), 463−471 doi: 10.1007/s13233-010-0512-2
21. [21]
  Liu, H. Z.; Chen, F.; Liu, B.; Estep, G.; Zhang, J. W. Super toughened poly(lactic acid) ternary blends by simultaneous dynamic vulcanization and interfacial compatibilization. Macromolecules 2010, 43(14), 6058−6066 doi: 10.1021/ma101108g
22. [22]
  Liu, H. Z.; Song, W. J.; Chen, F.; Guo, L.; Zhang, J. W. Interaction of microstructure and interfacial adhesion on impact performance of polylactide (PLA) ternary blends. Macromolecules 2011, 44(6), 1513−1522 doi: 10.1021/ma1026934
23. [23]
  Liu, H. Z.; Guo, X. J.; Song, W. J.; Zhang, J. W. Effects of metal ion type on ionomer-assisted reactive toughening of poly(lactic acid). Ind. Eng. Chem. Res. 2013, 52(13), 4787−4793 doi: 10.1021/ie303317k
24. [24]
  Megevand, B.; Pruvost, S.; Lins, L. C.; Livil, S.; Gérard, J. F.; Duchet-Rumeau, J. Probing nanomechanical properties with AFM to understand the structure and behavior of polymer blends compatibilized with ionic liquids. RSC Adv. 2016, 6(98), 96421−96430 doi: 10.1039/C6RA18492H
25. [25]
  Lins, L. C.; Livi, S.; Duchet-Rumeau, J.; Gérard, J. F. Phosphonium ionic liquids as new compatibilizing agents of biopolymer blends composed of poly(butylene-adipate-co-terephtalate)/poly(lactic acid) (PBAT/PLA). RSC Adv. 2015, 5(73), 59082−59092 doi: 10.1039/C5RA10241C
26. [26]
  Wang, P.; Zhang, D.; Zhou, Y. Y.; Li, Y.; Fang, H. G.; Wei, H. B.; Ding, Y. S. A well-defined biodegradable 1,2,3-triazolium-functionalized PEG-b-PCL block copolymer: facile synthesis and its compatibilization for PLA/PCL blends. Ionics 2018, 10.1007/s11581-017-2234-3 doi: 10.1007/s11581-017-2234-3
27. [27]
  Jérémy, O.; Jean-Marie, R.; Cédric, S.; Sophie, B.; Apostolos, E.; Dubois, P.; Giannelis, E. P. Shape-memory behavior of polylactide/silica ionic hybrids. Macromolecules 2017, 50(7), 2896−2905 doi: 10.1021/acs.macromol.7b00195
28. [28]
  Livi, S.; Duchet-Rumeau, J.; Gérard, J. F.; Pham, T. N. Polymers and ionic liquids: a successful wedding. Macromol. Chem. Phys. 2015, 216(4), 359−368 doi: 10.1002/macp.v216.4
29. [29]
  Chen, B. K.; Wu, T. Y.; Chang, Y. M.; Chen, A. F. Ductile polylactic acid prepared with ionic liquids. Chem. Eng. J. 2013, 215-216, 886−893 doi: 10.1016/j.cej.2012.11.078
30. [30]
  Gardella, L.; Furfaro, D.; Galimberti, M.; Monticelli, O. On the development of facile approach based on the use of ionic liquids: preparation of PLLA (sc-PLA)/high surface area nano-graphite systems. Green Chem. 2015, 17(7), 4082−4088 doi: 10.1039/C5GC00964B
31. [31]
  Cui, J.; Nie, F. M.; Yang, J. X.; Pan, L.; Ma, Z.; Li, Y. S. Novel imidazolium-Based poly(ionic liquid)s with different counter ions for self-healing. J. Mater. Chem. A 2017, 5, 25220−25229 doi: 10.1039/C7TA06793C
32. [32]
  Le, H. H.; Das, A. Triggering the self-healing properties of modifed bromobutyl rubber by intrinsically electrical heating. Macromol. Mater. Eng. 2017, 302, 1600385 doi: 10.1002/mame.201600385
33. [33]
  Das, A.; Sallat, A.; Böhme, F.; Suckow, M.; Basu, D.; Wießner, S.; Stöckelhuber, K. W.; Voit, B.; Heirich, G. Ionic modification turns commercial rubber into a self-healing material. ACS Appl. Mater. Interfaces 2015, 7(37), 20623−20630 doi: 10.1021/acsami.5b05041
34. [34]
  Suckow, M.; Mordvinkin, A.; Roy, M.; Singha, N. K.; Heinrich, G.; Voit, B.; Saalwächter, K.; Böhme, F. Tuning the properties and self-healing behavior of ionically modified poly(isobutylene-co-isoprene) rubber. Macromolecules 2018, 51(2), 468−479 doi: 10.1021/acs.macromol.7b02287
35. [35]
  Meng, Q. Q.; Wang, B.; Pan, L.; Li, Y. S.; Ma, Z. Synthesis and properties of isotactic polypropylene ionomers containing ammonium Ions. Acta Polymerica Sinica (in Chinese) 2017, 11, 1762−1772
36. [36]
  Lee, M.; Choi, U. H.; Wi, S.; Slebodnick, C.; Colby, R. H.; Gibson, H. W. 1,2-Bis[N-(N′-alkylimidazolium)] ethane salts: a new class of organic ionic plastic crystals. J. Mater. Chem. 2011, 21(33), 12280−12287 doi: 10.1039/c1jm10995b
37. [37]
  Dakin, J. M.; Shanmugam, K. V. S.; Twigg, C.; Whitney, R. A.; Parent, J. S. Isobutylene-rich macromonomers: dynamics and yields of peroxide-initiated crosslinking. Polym. Chem. 2015, 53(1), 123−132 doi: 10.1002/pola.27462
38. [38]
  Parent, J. S.; Porter, A. M. J.; Kleczek, M. R.; Whitney, R. A. Imidazolium bromide derivatives of poly(isobutylene-co-isoprene): a new class of elastomeric ionomers. Polymer 2011, 52(24), 5410−5418 doi: 10.1016/j.polymer.2011.10.021
39. [39]
  Kim, A.; Miller, K. M. Synthesis and thermal analysis of crosslinked imidazolium-containing polyester networks prepared by Michael addition polymerization. Polymer 2012, 53(25), 5666−5674 doi: 10.1016/j.polymer.2012.10.040
40. [40]
  Ye, Y. S.; Sharick, S.; Davis, E. M.; Winey, K. I.; Elabd, Y. A. High hydroxide conductivity in polymerized ionic liquid block copolymers. ACS Macro Lett. 2013, 2(7), 575−580 doi: 10.1021/mz400210a
41. [41]
  Nykaza, J. R.; Ye, Y. S.; Elabd, Y. A. Polymerized ionic liquid diblock copolymers with long alkyl side-chain length. Polymer 2014, 55(16), 3360−3369 doi: 10.1016/j.polymer.2014.04.003
42. [42]
  Wu, J. R.; Huang, G. S.; Pan, Q. Y.; Zheng, J.; Zhu, Y. C.; Wang, B. An investigation on the molecular mobility through the glass transition of chlorinated butyl rubber. Polymer 2007, 48(26), 7653−7659 doi: 10.1016/j.polymer.2007.11.006
43. [43]
  Mora-Barrantes, I.; Malmierica, M. A.; Valentin, J. L.; Rodriguez, A.; Ibarra, L. Effect of covalent cross-links on the network structure of thermo-reversible ionic elastomers. Soft Matter 2012, 8(19), 5201−5213 doi: 10.1039/c2sm06975j
44. [44]
  Marin, N.; Favis, B. D. Co-continuous morphology development in partially miscible PMMA/PC blends. Polymer 2002, 43(17), 4723−4731 doi: 10.1016/S0032-3861(02)00280-X
45. [45]
  Harrats, C.; Thomas, S. and Groeninckx, G. " Micro- and nanostructured multiphase polymer blends system”, CRC Press, 2006, p. 4-33.
46. [46]
  Phetwarotai, W.; Tanrattanakul, V.; Phusunti, N. Synergistic effect of nucleation and compatibilization on the polylactide and poly(butylene adipate-co-terephthalate) blend films. Chinese J. Polym. Sci. 2016, 34(9), 1129−1140 doi: 10.1007/s10118-016-1834-0
47. [47]
  Nagarajan, V. Overcoming the fundamental challenges in improving the impact strength and crystallinity of PLA biocomposites: influence of nucleating agent and mold temperature. ACS Appl. Mater. Interfaces 2015, 7(21), 11203−11214 doi: 10.1021/acsami.5b01145
48. [48]
  Yu, F.; Huang, H. X. Simultaneously toughening and reinforcing poly(lactic acid)/thermoplastic polyurethane blend via enhancing interfacial adhesion by hydrophobic silica nanoparticles. Polym. Test. 2015, 45, 107−113 doi: 10.1016/j.polymertesting.2015.06.001
49. [49]
  Zhang, K. Y.; Mohanty, A. K.; Misra, M. Fully biodegradable and biorenewable ternary blends from polylactide, poly(3-hydroxybutyrate-co-hydroxyvalerate) and poly(butylene succinate) with balanced properties. ACS Appl. Mater. Interfaces 2012, 4(6), 3091−3101 doi: 10.1021/am3004522
50. [50]
  Zhang, K. Y.; Nagarajan, V.; Misra, M.; Mohanty, A. K. Super toughened renewable PLA reactive multiphase blends system: phase morphology and performance. ACS Appl. Mater. Interfaces 2014, 6(15), 12436−12448 doi: 10.1021/am502337u
1. [1]
  Weijian Zhang , Xianyu Deng , Liying Wang , Jian Wang , Xiuting Guo , Lianggui Huang , Xinyi Wang , Jun Wu , Linjia Jiang . Poly(ferulic acid) nanocarrier enhances chemotherapy sensitivity of acute myeloid leukemia by selectively targeting inflammatory macrophages. Chinese Chemical Letters, 2024, 35(9): 109422-. doi: 10.1016/j.cclet.2023.109422
2. [2]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
3. [3]
  Shuxin Liu , Jinjuan Ma , Aiguo Wang , Nan Zheng . Decomposable and sono-enzyme co-triggered poly(sonosensitizers) for precise and hypotoxic sonodynamic therapy. Chinese Chemical Letters, 2025, 36(4): 110032-. doi: 10.1016/j.cclet.2024.110032
4. [4]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
5. [5]
  Xinyu Liu , Jialin Yang , Zonglin He , Jiaoyan Ai , Lina Song , Baohua Liu . Linear polyurethanes with excellent comprehensive properties from poly(ethylene carbonate) diol. Chinese Chemical Letters, 2025, 36(1): 110236-. doi: 10.1016/j.cclet.2024.110236
6. [6]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
7. [7]
  Di Wang , Qing-Song Chen , Yi-Ran Lin , Yun-Xin Hou , Wei Han , Juan Yang , Xin Li , Zhen-Hai Wen . Tuning strategies and electrolyzer design for Bi-based nanomaterials towards efficient CO2 reduction to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(8): 100346-100346. doi: 10.1016/j.cjsc.2024.100346
8. [8]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
9. [9]
  Mengyuan Li , Xitong Ren , Yanmei Gao , Mengyao Mu , Shiping Zhu , Shufang Tian , Minghua Lu . Constructing bifunctional magnetic porous poly(divinylbenzene) polymer for high-efficient removal and sensitive detection of bisphenols. Chinese Chemical Letters, 2024, 35(12): 109699-. doi: 10.1016/j.cclet.2024.109699
10. [10]
  Haibo Ye , Qianyu Li , Juan Li , Didi Li , Zhimin Ao . Review on the abiotic degradation of biodegradable plastic poly(butylene adipate-terephthalate): Mechanisms and main factors of the degradation. Chinese Chemical Letters, 2025, 36(1): 109861-. doi: 10.1016/j.cclet.2024.109861
11. [11]
  Yaxuan Jin , Chao Zhang , Guigang Zhang . Atomically dispersed low-valent Au on poly(heptazine imide) boosts photocatalytic hydroxyl radical production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100414-100414. doi: 10.1016/j.cjsc.2024.100414
12. [12]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
13. [13]
  Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H₂O₂ photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
14. [14]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
15. [15]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
16. [16]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
17. [17]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
18. [18]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
19. [19]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
20. [20]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(898)
HTML views(38)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142