Citation: Wei Zhao, Chuan-Yang Li, Chun-Ji Wu, Xin-Li Liu, Ze-Huai Mou, Chang-Guang Yao, Dong-Mei Cui. Synthesis of Ultraviolet Absorption Polylactide via Immortal Polymerization of rac-Lactide Initiated by a Salan-yttrium Catalyst[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 202-206. doi: 10.1007/s10118-018-2050-x shu

Synthesis of Ultraviolet Absorption Polylactide via Immortal Polymerization of rac-Lactide Initiated by a Salan-yttrium Catalyst

Wei Zhao ^a,c,† ,
Chuan-Yang Li ^a,b,† ,
Chun-Ji Wu ^a ,
Xin-Li Liu ^a ,
Ze-Huai Mou ^a,b ,
Chang-Guang Yao ^a,b ,
Dong-Mei Cui ^a,,

a.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
University of Chinese Academy of Sciences, Changchun Branch, Changchun 130022, China
c.
College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China

Corresponding author: Dong-Mei Cui, dmcui@ciac.ac.cn

^†

Received Date: 6 September 2017
Accepted Date: 22 September 2017
Available Online: 27 November 2017

A highly efficient strategy for the synthesis of polylactide with the UV absorption ability was established by employing a Salan-yttrium complex (acting as a fast runing catalyst) combined with large excess hydroxyl functionalized benzophenone, BP'-OH. During polymerization, BP'-OH, acting as the chain transfer agent, attached to the active rare-earth metal catalyst via a rapid-reversible exchange reaction to initiate the polymerization. Thus, more polyester chains appeared to grow from one active metal species, and the UV absorption fragments were incorporated into the polymer chains at specific sites, in situ. A high productivity up to 1000 mol_LA/mol_(Salan-Y) was successfully achieved and 100 BP'-labeled PLA chains grew from each active metal center.
- Yttrium catalyst,
- Ring-opening polymerization,
- Polylactide,
- Ultraviolet absorption
1. [1]
  Drumright R. E., Gruber P. R., Henton D. E.. Polylactic acid technology[J]. Adv. Mater., 2000,12:1841-1846. doi: 10.1002/(ISSN)1521-4095
2. [2]
  Mecking S.. Nature or Petrochemistry? Biologically degradable materials[J]. Angew. Chem. Int. Ed., 2004,43:1078-1085. doi: 10.1002/(ISSN)1521-3773
3. [3]
  Dattaa R., Tsaia S. P., Bonsignorea P., Moona S. H., Frank J. R.. Technological and economic potential of poly(lactic acid) and lactic acid derivatives[J]. FEMS Microbiol. Rev., 1995,16:221-231. doi: 10.1111/fmr.1995.16.issue-2-3
4. [4]
  Auras R., Harte B., Selke S.. An overview of polylactides as packaging materials[J]. Macromol. Biosci., 2004,4:835-864. doi: 10.1002/(ISSN)1616-5195
5. [5]
  Nelson K. H., Cathcart W. M.. Transmission of light through pigmented polyethylene milk bottles[J]. J. Food Prot., 1984,47:346-348. doi: 10.4315/0362-028X-47.5.346
6. [6]
  Erickson M. C.. Chemical and microbial stability of fluid milk in response to packaging and dispensing[J]. Int. J. Dairy Technol., 1997,50:107-111. doi: 10.1111/idt.1997.50.issue-3
7. [7]
  Bradley R. L.. Effect of light on alteration of nutritional value and flavor of milk:a review[J]. J. Food Prot., 1980,43:314-320. doi: 10.4315/0362-028X-43.4.314
8. [8]
  Xiao P., Shi S. Q., Nie J.. Synthesis and characterization of copolymerizable one-component type Ⅱ photoinitiator[J]. Polym. Adv. Technol.,, 2008,19:1305-1310. doi: 10.1002/pat.v19:9
9. [9]
  Wu Q. H., Qu B. J.. Photoinitiating characteristics of benzophenone derivatives as new initiators in the photocrosslinking of polyethylene[J]. Polym. Eng. Sci., 2001,41:1220-1226. doi: 10.1002/(ISSN)1548-2634
10. [10]
  Xiao P., Wang Y., Dai M., Shi S., Wu G., Nie J.. Synthesis and photopolymerization kinetics of polymeric one-component type Ⅱ photoinitiator containing benzophenone moiety and tertiary amine[J]. Polym. Eng. Sci., 2008,48:884-888. doi: 10.1002/(ISSN)1548-2634
11. [11]
  Han J. Y., Jiang S. L., Gao Y. J., Sun F.. Intramolecularinitiating photopolymerization behavior of nanogels with the capability of reducing shrinkage[J]. J. Mater. Chem. C, 2016,4:10675-10683. doi: 10.1039/C6TC03839E
12. [12]
  Gritsenko K. P., Krasovsky A. M.. Thin-film deposition of polymers by vacuum degradation[J]. Chem. Rev., 2003,103:3607-3650. doi: 10.1021/cr010449q
13. [13]
  Zhao W., Li C. Y., Liu B., Wang X., Li P., Wang Y., Wu C. J., Yao C. G., Liu X. L., Cui D. M.. A new strategy to access polymers with aggregation-induced emission characteristics[J]. Macromolecules, 2014,47:5586-5594. doi: 10.1021/ma500985j
14. [14]
  Liu X. L., Shang X. M., Tang T., Hu N. H., Pei F. K., Cui D. M., Chen X. S., Jing X. B.. Achiral lanthanide alkyl complexes bearing N, O multidentate ligands. synthesis and catalysis of highly heteroselective ring-opening polymerization of rac-lactide[J]. Organometallics, 2007,26:2747-2757. doi: 10.1021/om0700359
15. [15]
  Wang Y., Zhao W., Liu X. L., Cui D. M., Chen E. Y. X.. Ligand-free magnesium catalyst system:immortal polymerization of L-lactide with high catalyst efficiency and structure of active intermediates[J]. Macromolecules, 2012,45:6957-6965. doi: 10.1021/ma3007625
16. [16]
  Zhao W., Cui D. M., Liu X. L., Chen X. S.. Facile Synthesis of Hydroxyl-ended, highly stereoregular, star-shaped poly(lactide) from immortal ROP of rac-Lactide and kinetics study[J]. Macromolecules, 2010,43:6678-6684. doi: 10.1021/ma101202g
17. [17]
  Zhao W., Liu B., Liu X. L., Wang X., Wang Y., Yao C. G., Wu C. J., Cui D. M.. Neutral lutetium complex/polyamine mediated immortal ring-opening polymerization of rac-lactide:facile synthesis of well-defined hydroxyl-end and amide-core stereoregular star polylactide[J]. Polym. Chem,, 2015,6:7711-7716. doi: 10.1039/C5PY01164G
18. [18]
  Li C. Y., Liu X. L., He S. S., Huang Y. B., Cui D. M.. Synthesis and AIE properties of PEG-PLA-PMPC based triblock amphiphilic biodegradable polymers[J]. Polym. Chem,, 2016,7:1121-1128. doi: 10.1039/C5PY01849H
19. [19]
  Amgoune A., Thomas C. M., Roisnel T., Carpentier J. F.. Ring-opening polymerization of lactide with group 3 metal complexes supported by dianionic alkoxy-amino-bisphenolate ligands:combining high activity, productivity, and selectivity[J]. Chem. Eur. J., 2006,12:169-179. doi: 10.1002/(ISSN)1521-3765
20. [20]
  Ma H., Okuda J.. Kinetics and mechanism of L-lactide polymerization by rare earth metal silylamido complexes:effect of alcohol addition[J]. Macromolecules, 2005,38:2665-2673. doi: 10.1021/ma048284l
21. [21]
  Ajellal N., Lyubov D. M., Sinenkov M. A., Fukin G. K., Cherkasov A. V., Thomas C. M., Carpentier J. F., Trifonov A. A.. Bis(guanidinate) alkoxide complexes of lanthanides:synthesis, structures and use in immortal and stereoselective ring-opening polymerization of cyclic esters[J]. Chem. Eur. J., 2008,14:5440-5448. doi: 10.1002/(ISSN)1521-3765
22. [22]
  Cowman C. D., Padgett E., Tan K. W., Hovden R., Gu Y., Andrejevic N., Muller D., Coates G. W., Wiesner U.. Multicomponent nanomaterials with complex networked architectures from orthogonal degradation and binary metal backfilling in ABC triblock terpolymers[J]. J. Am. Chem. Soc., 2015,137:6026-6033. doi: 10.1021/jacs.5b01915
23. [23]
  Thevenon A., Romain C., Bennington M. S., White A. J. P., Davidson H. J., Brooker S., Williams C. K.. Dizinc lactide polymerization catalysts:hyperactivity by control of ligand conformation and metallic cooperativity[J]. Angew. Chem. Int. Ed., 2016,55:8680-8685. doi: 10.1002/anie.201602930
1. [1]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
2. [2]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
3. [3]
  Feng Zhao , Hongyu Ding , Ting Sun , Chao Shen , Zu-Li Wang , Wei Wei , Dong Yi . Visible-light-promoted multi-component carbene transfer reactions of diazo compounds via ring-opening of cyclic ethers. Chinese Chemical Letters, 2026, 37(2): 111834-. doi: 10.1016/j.cclet.2025.111834
4. [4]
  Junqi Su , Wenhao Liu , Jianjun Wang , Weifen Luo , Yangyang Ma , Leiyang Lv , Zhiping Li . Palladium-catalyzed ring-opening defluorinative cross-coupling of gem-difluorocyclopropanes with fluoromalonates or fluorobis(phenylsulfonyl)methane. Chinese Chemical Letters, 2026, 37(3): 111288-. doi: 10.1016/j.cclet.2025.111288
5. [5]
  Rong-Nan Yi , Jun Jiang , Wei-Min He . Pd/NHC-catalyzed ring-opening cross-coupling of gem-difluorocyclopropanes via a 3,3′-reductive elimination pathway. Chinese Chemical Letters, 2026, 37(4): 112163-. doi: 10.1016/j.cclet.2025.112163
6. [6]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
7. [7]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
8. [8]
  Jumei Zhang , Ziheng Zhang , Gang Li , Hongjin Qiao , Hua Xie , Ling Jiang . Ligand-mediated reactivity in CO oxidation of yttrium-nickel monoxide carbonyl complexes. Chinese Chemical Letters, 2025, 36(2): 110278-. doi: 10.1016/j.cclet.2024.110278
9. [9]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
10. [10]
  Sajid Hussain , Omer M.A. Dagah , Essam A.M.S Obaid , Peng Jin , Ovas Ahmed Dar , Muhammd Irfan , Yiming Qi , Qinghua Wu , Ming Jin , Tengli Zhang , Lei Luo . Chitosan as oral absorption enhancer and inhibitor: A comprehensive review. Chinese Chemical Letters, 2026, 37(1): 111273-. doi: 10.1016/j.cclet.2025.111273
11. [11]
  Cuiwu MO , Gangmin ZHANG , Chao WU , Zhipeng HUANG , Chi ZHANG . A(NH₂SO₃) (A=Li, Na): Two ultraviolet transparent sulfamates exhibiting second harmonic generation response. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1387-1396. doi: 10.11862/CJIC.20240045
12. [12]
  Hongyuan Sha , Dongling Yang , Yanran Shang , Zujian Wang , Rongbing Su , Chao He , Xiaoming Yang , Xifa Long . Trithionic guanidine: A novel semi-organic short-wave ultraviolet nonlinear optical sulfate with dimeric heteroleptic tetrahedra. Chinese Chemical Letters, 2025, 36(4): 109730-. doi: 10.1016/j.cclet.2024.109730
13. [13]
  Yangfeifei Ou , Xiao-Liang Zhou , You-Zhao Lan , Jian-Wen Cheng . Borosilicates as deep-ultraviolet transparent nonlinear optical crystals: Structural motifs, performance limits and future directions. Chinese Journal of Structural Chemistry, 2025, 44(9): 100708-100708. doi: 10.1016/j.cjsc.2025.100708
14. [14]
  Bing Zhang , Guoqing Jiang , Wenxin Shi , Yanei Xue , Wenjun Sun . Vacuum-ultraviolet technology photolysis of aqueous reaction systems for organic pollutants abatement. Chinese Chemical Letters, 2026, 37(2): 111371-. doi: 10.1016/j.cclet.2025.111371
15. [15]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
16. [16]
  Kang Wang , Qinglin Zhou , Weijin Li . Conductive metal-organic frameworks for electromagnetic wave absorption. Chinese Journal of Structural Chemistry, 2024, 43(10): 100325-100325. doi: 10.1016/j.cjsc.2024.100325
17. [17]
  Ju Wang , Yongbing Sun , Lingbang Meng , Jianfang Feng , Meng Cheng , Liangxing Tu . Intestinal transporters and oral absorption enhancing strategies based on these transporters. Chinese Chemical Letters, 2025, 36(5): 110529-. doi: 10.1016/j.cclet.2024.110529
18. [18]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
19. [19]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
20. [20]
  Lu Li , Suticha Chunta , Xianzi Zheng , Haisheng He , Wei Wu , Yi Lu . β-Lactoglobulin stabilized lipid nanoparticles enhance oral absorption of insulin by slowing down lipolysis. Chinese Chemical Letters, 2024, 35(4): 108662-. doi: 10.1016/j.cclet.2023.108662

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1920)
HTML views(52)

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