Citation: Yiyang Zhang, Guangshu Yuan, Xiangkun Meng, Xu Zhang, Lei Yu. Promoting the catalytic activities of polyanilines for L-lactic acid condensation by calcium-doping: A biocompatible strategy[J]. Chinese Chemical Letters, ;2025, 36(12): 111069. doi: 10.1016/j.cclet.2025.111069 shu

Promoting the catalytic activities of polyanilines for L-lactic acid condensation by calcium-doping: A biocompatible strategy

Yiyang Zhang ^{a, b, *,} ,
Guangshu Yuan ^b ,
Xiangkun Meng ^b ,
Xu Zhang ^b ,
Lei Yu ^{a, b, *,}

a.
School of Mechanical Engineering, Yangzhou University, Yangzhou 225127, China
b.
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China

008011@yzu.edu.cn

yulei@yzu.edu.cn

Received Date: 25 December 2024
Revised Date: 9 March 2025
Accepted Date: 11 March 2025
Available Online: 13 March 2025

Figures(7)

Polyanilines (PANIs) are easily accessible materials that can be employed to prepare catalysts for a variety of useful reactions. Investigations in the field are of profound academic and industrial values. In this work, we unexpectedly found that, calcium-doping could enhance the specific surface area and pore volume of poly-p-anisidine (PANI-OMe), so that the catalytic activity of the material could be significantly improved. It is notable that Ca-doping significantly enhanced the pore size of the material to 291.5 nm, making it a macroporous material that can allow even more sufficient contact of the catalytically active sites of nitrogen to contact with the macromolecules such as the PLA oligomer. Thus, the Ca-doped PANI-OMe (PANI-OMe/Ca) could well catalyse the condensation reaction of L-lactic acid to synthesize L-lactide in 75.0% yield with 98.2% optical purity at kilogram reaction scale. Since Ca is a biocompatible element that widely exists in both human and animal bodies, the Ca-doping protocol provides a biocompatible catalyst for L-lactide production. This is an important progress because L-lactide is widely employed as the basic raw material to produce the environment-friendly bio-degradable materials and the biomedical polymers. It may also inspire new strategies for designing the catalyst for the reactions involving macromolecular intermediates.
- Calcium,
- Polyaniline,
- L-Lactic acid,
- Lactide,
- Biocompatible materials,
- Polymer
1. [1]
  Z. Li, B.H. Tan, T. Lin, C. He, Prog. Polym. Sci. 62 (2016) 22–72. doi: 10.1016/j.progpolymsci.2016.05.003
2. [2]
  M. Dusselier, P.V. Wouwe, A. Dewaele, et al., Science 349 (2015) 78–80. doi: 10.1126/science.aaa7169
3. [3]
  C. Li, C. Guo, V. Fitzpatrick, et al., Nat. Rev. Mater. 5 (2020) 61–81.
4. [4]
  P.V. Wouwe, M. Dusselier, E. Vanleeuw, B. Sels, ChemSusChem 9 (2016) 907–921. doi: 10.1002/cssc.201501695
5. [5]
  M. Tummalapalli, S. Anjum, S. Kumari, B. Gupta, Polym. Rev. 56 (2016) 607–630. doi: 10.1080/15583724.2015.1119163
6. [6]
  X. Meng, L. Yu, Y. Cao, et al., Org. Biomol. Chem. 19 (2021) 10288–10295. doi: 10.1039/d1ob01918j
7. [7]
  X. Cui, X. Meng, Y. Chen, et al., Chin. J. Org. Chem. 42 (2022) 2954–2960. doi: 10.6023/cjoc202204045
8. [8]
  X. Meng, Z. Qi, L. Yu, Y. Zhang, Chin. J. Org. Chem. 43 (2023) 112–119. doi: 10.6023/cjoc202206051
9. [9]
  V. Botvin, S. Karaseva, V. Khasanov, Polym. Degrad. Stab. 182 (2020) 109382. doi: 10.1016/j.polymdegradstab.2020.109382
10. [10]
  W. Huang, Y. Qi, N. Cheng, et al., Polym. Degrad. Stab. 101 (2014) 18–23. doi: 10.1016/j.polymdegradstab.2014.01.022
11. [11]
  H.Y. Song, J. Jiang, C. Wu, et al., Green Chem. 25 (2023) 3292–3296. doi: 10.1039/d2gc04843d
12. [12]
  Z. Wei, M. Wan, Adv. Mater. 14 (2002) 1314–1317. doi: 10.1002/1521-4095(20020916)14:18<1314::AID-ADMA1314>3.0.CO;2-9
13. [13]
  C.O. Baker, X. Huang, W. Nelsonc, R.B. Kaner, Chem. Soc. Rev. 46 (2017) 1510–1525. doi: 10.1039/C6CS00555A
14. [14]
  J. Wu, Q. Zhang, J. Wang, et al., Energy Environ. Sci. 11 (2018) 1280–1286. doi: 10.1039/c8ee00078f
15. [15]
  Z. Duan, K. Deng, C. Li, et al., Chem. Eng. J. 428 (2022) 132646. doi: 10.1016/j.cej.2021.132646
16. [16]
  Z. Zeng, Y. Chen, X. Zhu, L. Yu, Chin. Chem. Lett. 34 (2023) 107728. doi: 10.1016/j.cclet.2022.08.008
17. [17]
  W. Li, F. Wang, Y. Shi, L. Yu, Chin. Chem. Lett. 34 (2023) 107505. doi: 10.1016/j.cclet.2022.05.019
18. [18]
  Y. Chen, Y. Zhang, H. Zhou, L. Yu, ACS Appl. Mater. Interfaces 16 (2024) 37906–37914. doi: 10.1021/acsami.4c05028
19. [19]
  Y. Liu, D. Tang, K. Cao, et al., J. Catal. 360 (2018) 250–260. doi: 10.1016/j.jcat.2018.01.026
20. [20]
  J. Xiong, Q. Wu, X. Mei, et al., ACS Catal. 8 (2018) 7915–7930. doi: 10.1021/acscatal.8b01924
21. [21]
  W. Li, Y. Tian, C. Zhao, et al., Chem. Eng. J. 303 (2016) 282–291. doi: 10.1016/j.cej.2016.06.022
22. [22]
  X. Meng, Y. Zhang, H. Zhou, L. Yu, ACS Sustain. Chem. Eng. 10 (2022) 7658–7663. doi: 10.1021/acssuschemeng.2c01540
23. [23]
  N. Wang, J. Feng, J. Chen, et al., Chem. Eng. J. 316 (2017) 33–40. doi: 10.1016/j.cej.2017.01.066
24. [24]
  H. Xu, J. Tang, Y. Chen, et al., J. Electron. Mater. 46 (2017) 6150–6157. doi: 10.1007/s11664-017-5638-y
25. [25]
  L. Shi, R.P. Liang, J.D. Qiu, J. Mater. Chem. 22 (2012) 17196–17203. doi: 10.1039/c2jm31859h
26. [26]
  F.Z. Kouidri, I. Moulefera, S. Bahoussi, et al., Colloid Polym. Sci. 299 (2021) 1075–1083. doi: 10.1007/s00396-021-04837-2
27. [27]
  G. Sharma, D. Pathania, M. Naushad, N.C. Kothiyal, Chem. Eng. J. 251 (2014) 413–421. doi: 10.1016/j.cej.2014.04.074
28. [28]
  Y. Chen, Q. Wu, Colloids Surf. A: Physicochem. Eng. Asp. 325 (2008) 33–37. doi: 10.1016/j.colsurfa.2008.04.041
29. [29]
  S.L. Patil, S.G. Pawar, M.A. Chougule, et al., Int. J. Polym. Mater. Polym. Biomater. 61 (2012) 809–820. doi: 10.1080/00914037.2011.610051
30. [30]
  H.C. Pant, M.K. Patra, S.C. Negi, et al., Bull. Mater. Sci. 29 (2006) 379–384. doi: 10.1007/BF02704139
31. [31]
  D. Balasubramanian, B. Raman, C. Sivakama Sundari, J. Am. Chem. Soc. 115 (1993) 74–77. doi: 10.1021/ja00054a010
32. [32]
  M. Niederberger, Acc. Chem. Res. 40 (2007) 793–800. doi: 10.1021/ar600035e
33. [33]
  J. Yue, A.J. Epstein, Macromolecules 24 (1991) 4441–4445. doi: 10.1021/ma00015a030
34. [34]
  E. Kang, K. Neoh, K.L. Tan, Polym. Commun. 32 (1991) 412–414.
35. [35]
  F.Y. Chuang, S.M. Yang, J. Colloid Interface Sci. 320 (2008) 194–201. doi: 10.1016/j.jcis.2008.01.015
36. [36]
  X.L. Wei, M. s Fahlman, A.J. Epstein, Macromolecules 32 (1999) 3114–3117. doi: 10.1021/ma981386p
37. [37]
  G. Kowalski, J. Pielichowski, M. Grzesik, Sci. World J. 2014 (2014) 648949.
38. [38]
  B. Jiang, X. Tantai, L. Zhang, et al., RSC Adv. 5 (2015) 50747–50755. doi: 10.1039/C5RA05073A
39. [39]
  M. Ghadamyari, S. Chaemchuen, K. Zhou, et al., Catal. Commun. 114 (2018) 33–36. doi: 10.1016/j.catcom.2018.06.003
40. [40]
  Y. Zhang, Y. Qi, Y. Yin, et al., ACS Sustain. Chem. Eng. 8 (2020) 2865–2873. doi: 10.1021/acssuschemeng.9b06987
41. [41]
  J.C. Hou, W. Cai, H.T. Ji, et al., Chin. Chem. Lett. 36 (2025) 110469. doi: 10.1016/j.cclet.2024.110469.crossref.org/guestquery?queryType=xml&restype=unixref&xml=|Physics of Plasmas||18|11|113502|2011|||
42. [42]
  H.T. Ji, Y.H. Lu, Y.T. Liu, et al., Chin. Chem. Lett. 36 (2025) 110568. doi: 10.1016/j.cclet.2024.110568
43. [43]
  Y.H. Lu, C. Wu, J.C. Hou, ACS Catal. 13 (2023) 13071–13076. doi: 10.1021/acscatal.3c02268
1. [1]
  Huimin Gao , Zhuochen Yu , Xuze Zhang , Xiangkun Yu , Jiyuan Xing , Youliang Zhu , Hu-Jun Qian , Zhong-Yuan Lu . A mini review of the recent progress in coarse-grained simulation of polymer systems. Chinese Journal of Structural Chemistry, 2024, 43(5): 100266-100266. doi: 10.1016/j.cjsc.2024.100266
2. [2]
  Guanxiong Yu , Chengkai Xu , Huaqiang Ju , Jie Ren , Guangpeng Wu , Chengjian Zhang , Xinghong Zhang , Zhen Xu , Weipu Zhu , Hao-Cheng Yang , Haoke Zhang , Jianzhao Liu , Zhengwei Mao , Yang Zhu , Qiao Jin , Kefeng Ren , Ziliang Wu , Hanying Li . Key progresses of MOE key laboratory of macromolecular synthesis and functionalization in 2023. Chinese Chemical Letters, 2024, 35(11): 109893-. doi: 10.1016/j.cclet.2024.109893
3. [3]
  Yuhan Wu , Qing Zhao , Zhijie Wang . Layered vanadium oxides: Promising cathode materials for calcium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(5): 100271-100271. doi: 10.1016/j.cjsc.2024.100271
4. [4]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
5. [5]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
6. [6]
  Xiaoyi Sun , Duohang Bi , Hankun Qiao , Yijing Liu , Jintao Zhu . Painless Injection: Microneedles Revolutionizing Beauty and Health Brought. University Chemistry, 2025, 40(10): 166-174. doi: 10.12461/PKU.DXHX202411006
7. [7]
  Wen-Bing Hu . Systematic Introduction of Polymer Chain Structures. University Chemistry, 2025, 40(4): 15-19. doi: 10.3866/PKU.DXHX202401014
8. [8]
  Haiyang Peng , Zhipeng Xie , Shuiqing Lu , Da Zhang , Bin Yang , Feng Liang . Dual-functionality composites of polyaniline-coated oxidized carbon nanohorns: Efficient wave absorption and enhanced corrosion resistance. Chinese Chemical Letters, 2025, 36(6): 110818-. doi: 10.1016/j.cclet.2025.110818
9. [9]
  Xiujuan Qiao , Zhenying Xu , Zhen Wei , Yiting Hou , Fengxian Gao , Xijuan Yu , Xiliang Luo . A wearable electrochemical biosensor based on antifouling and conducting polyaniline hydrogel for cortisol detection in sweat. Chinese Chemical Letters, 2025, 36(11): 110884-. doi: 10.1016/j.cclet.2025.110884
10. [10]
  Yunzhe Du , Siliu Cheng , Shuyi Li , Junping Niu , Yuan Gou , Ligang Yan , Tian-Xing Zhang , Ruijun Xie , Limin Han , Tiezheng Jia , Ning Zhu . C2-Transformation of calcium carbide trigered by hydrogen sulfide. Chinese Chemical Letters, 2025, 36(12): 111233-. doi: 10.1016/j.cclet.2025.111233
11. [11]
  Xinyu You , Xin Zhang , Shican Jiang , Yiru Ye , Lin Gu , Hexun Zhou , Pandong Ma , Jamal Ftouni , Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265
12. [12]
  Haoyu Luo , Jinsong Chen , Mengfei Luo , Hui Ma , Shengyan Pu . Heterogeneous Fenton catalytic degradation of nitrobenzene by controlled-release nano calcium peroxide. Chinese Chemical Letters, 2025, 36(6): 110367-. doi: 10.1016/j.cclet.2024.110367
13. [13]
  Xiaoman Dang , Zhiying Wu , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Highly robust supramolecular polymer networks crosslinked by metallacycles. Chinese Chemical Letters, 2024, 35(12): 110208-. doi: 10.1016/j.cclet.2024.110208
14. [14]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
15. [15]
  Yi Cao , Xiaojiao Ge , Yuanyuan Wei , Lulu He , Aiguo Wu , Juan Li . Tumor microenvironment-activatable neuropeptide-drug conjugates enhanced tumor penetration and inhibition via multiple delivery pathways and calcium deposition. Chinese Chemical Letters, 2024, 35(4): 108672-. doi: 10.1016/j.cclet.2023.108672
16. [16]
  Mimi Wu , Shoufeng Tang , Zhibin Wang , Qingrui Zhang , Deling Yuan . Molybdenum carbide activated calcium sulfite for antibiotic decontamination at near-neutral pH: Dissolved oxygen promoted bisulfite adsorption for singlet oxygen generation. Chinese Chemical Letters, 2025, 36(8): 110613-. doi: 10.1016/j.cclet.2024.110613
17. [17]
  Tiankai Sun , Hui Min , Zongsu Han , Liang Wang , Peng Cheng , Wei Shi . Rapid detection of nanoplastic particles by a luminescent Tb-based coordination polymer. Chinese Chemical Letters, 2024, 35(5): 108718-. doi: 10.1016/j.cclet.2023.108718
18. [18]
  Mengjun Sun , Zhi Wang , Jvhui Jiang , Xiaobing Wang , Chuang Yu . Gelation mechanisms of gel polymer electrolytes for zinc-based batteries. Chinese Chemical Letters, 2024, 35(5): 109393-. doi: 10.1016/j.cclet.2023.109393
19. [19]
  Dong Lv , Xuelei Liu , Wei Li , Qiang Zhang , Xinhong Yu , Yanchun Han . Single droplet formation by controlling the viscoelasticity of polymer solutions during inkjet printing. Chinese Chemical Letters, 2024, 35(6): 109401-. doi: 10.1016/j.cclet.2023.109401
20. [20]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(18)
HTML views(8)

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