Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance★

doi:10.6023/A23050206

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (11): 1551-1565.DOI: 10.6023/A23050206 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

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模块化双功能有机硼氮和硼磷催化体系的设计及其催化转化^★

杨贯文, 伍广朋^*()

浙江大学高分子科学与工程学系杭州 310058

投稿日期:2023-05-05 发布日期:2023-07-20

作者简介:

杨贯文, 博士, 浙江大学高分子系副研究员. 本科毕业于济南大学; 硕士毕业于大连理工大学徐铁齐教授课题组; 博士毕业于浙江大学, 导师为伍广朋教授. 在浙江大学化学流动站完成博士后研究后, 加入浙江大学高分子系开展可降解高分子材料的无金属化合成方面的学术研究.

伍广朋, 浙江大学求是特聘教授, 国家杰出青年基金获得者, 教育部青年长江学者. 本科毕业于山东轻工业学院(齐鲁工业大学), 博士毕业于大连理工大学, 师从吕小兵教授; 之后在美国得州农工大学、芝加哥大学经历两站博士后研究, 2015年9月加入浙江大学高分子系, 目前主要开展高分子合成化学、可降解高分子材料、光刻胶等方面的研究.

^★庆祝《化学学报》创刊90周年.

基金资助:
国家自然科学基金(22101253); 国家杰出青年科学基金(T2225004)

Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance^★

Guan-Wen Yang, Guang-Peng Wu()

Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310058

Received:2023-05-05 Published:2023-07-20
Contact: *E-mail: gpwu@zju.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(22101253); National Science Fund for Distinguished Young Scholars(T2225004)

Organoboron compounds are a class of non-metallic catalysts that have been extensively studied in recent years and have shown excellent applicability for ring-opening homopolymerization of epoxides and copolymerization of epoxides with other comonomers. However, the binary electrophile/nucleophile catalytic systems often have reduced activity or be deactivated due to the entropic disadvantage under dilute conditions, and it is also difficult to afford polymer materials with high molecular weight. This paper reviews the progress of bifunctional organoboron-quaternary ammonium/phosphonium salt catalytic systems containing both electrophilic and nucleophilic centers in one molecule that was designed by our group, focuses on the design concepts and principles of such bifunctional organoboron catalysts, compares the polymerization mechanisms between bifunctional and binary organoboron catalytic systems, and summarizes the use of bifunctional organoboron catalysts in the ring-opening polymerization of epoxides to prepare aliphatic polyethers, the copolymerization of epoxides and carbon dioxide/cyclic anhydride to prepare polycarbonates/polyesters. The future and trend of organoboron catalysts in polymer chemistry were prospected.

Key words: organoboron, Lewis pair, ring-opening polymerization, carbon dioxide, catalyst

Cite this article

Guan-Wen Yang, Guang-Peng Wu. Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance^★[J]. Acta Chimica Sinica, 2023, 81(11): 1551-1565.

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Fig. & Tab. 24

Figure 1. The binary and bifunctional Schiff base cobalt complex catalytic systems that the author has participated in regarding copolymerization of carbon dioxide and epoxides[17-18]

Figure 2. Gnanou, Feng, Hadjichristidis et al. reported triethylborane/onium salt binary catalytic system for epoxides-carbon dioxide copolymerization and the involved catalytic mechanism[19]

Figure 3. We reported (a) the design strategy for dynamic Lewis multicore system (DLMCS) systems, (b) synthetic steps, and (c) the representative mono-, di, tri- and tetranuclear bifunctional organoborane catalyst system. A represents the nitrogen or phosphorus atom; B represents the boron atom; X represents the halogen ions or other anions[25-26]

Figure 4. The mononuclear bifunctional organoboron catalysts for the copolymerization of cyclohexane epoxide with carbon dioxide[27]

Figure 5. (a) The binary catalytic system 8/BTEAB and the bifunctional catalyst 3b. (b) The catalytic performances of 8/BTEAB and 3b at different catalyst loadings[27]

Figure 6. The 11B NMR spectra for borane 8, the binary 8/BTEAB catalyst system (1/1, mole ratio) and the bifunctional catalyst 3b[27]

Figure 7. The optimized structure of catalyst 3b determined by DFT computational study[27]

Figure 8. Proposed mechanism based on mononuclear bifunctional organoboron-mediated CO2/CHO copolymerization[27]

Figure 9. The 11B NMR spectra of catalyst 9 and its intermediate reacting with CHO[28]

Figure 10. The proposed mechanism of the mononuclear organoboron catalyst-mediated ROP of BBL[34]

Figure 11. The mononuclear organoboron catalyst 10 for ROCOP of epoxides with CO2[37]

Figure 12. The dinuclear organoboron catalysts 11~13 for ROP of epoxides[49]

Figure 13. (a) The bifunctional and the control binary catalysts and the comparison of their catalytic activities for the ROP of PO. (b) 11B NMR spectra study[49]

Figure 14. The proposed intramolecular ammonium cation (N+) assisted SN2 mechanism based on the dinuclear organoboron-mediated ROP of PO[49]

Figure 15. Structure optimization of binuclear organoborane catalysts[36]

Figure 16. (a) The possible -ABB- linkage of CO2/PO copolymer. (b) Polymer hydrolysis-derived experiment and the crystalline structure of the obtained compounds[52] (a) The possible -ABB- linkage of CO2/PO copolymer. (b) Polymer hydrolysis-derived experiment and the crystalline structure of the obtained compounds[52]

Figure 17. (a) Crystal structures of 23?2DMF, 12?2DMF, 24?2DMF and 25?2DMF. (b) The relationship between B…B separation (d) and B—N+—B angle (θ). (c) The linear correlations between polymer sequence selectivity and B—N+—B angle (θ)[52]

Figure 18. (a) The ROCOP of ECH and CO2 and product selectivity. (b) The bifunctional Salen-Co (III) catalyst. (c) The formation route of cyclic carbonate. (d) Photographs of the crude polymer solution and the purified polymer using Salen-Co(III). (e) Chemical structure of the tetranuclear organoboron catalyst 26. (f) Crystal structure of 26b?4DMF. (g) Photographs of the crude polymer solution and the purified polymer using catalyst 26[59]

Figure 19. The proposed cyclically sequential copolymerization mechanism based on catalyst 26-mediated ROCOP of ECH with CO2[59]

Figure 20. The multinuclear bifunctional organoboron catalysts reported in recent literatures

Figure 21. The comparison of catalytic activity of organoboron-phos- phonium and organoboron-ammonium catalysts for the ROCOP of CHO with PA[65]

Figure 22. The optimized structures of (a) organoboron-phosphonium catalyst and (b) organoboron-ammonium catalyst determined by the DFT computational study[65]

Figure 23. The mononuclear organoboron catalyst containing phosphonium salt and its transition state structure of the copolymerization of CHO with CO2 as reported by Exxon Mobil Corporation[69]

Figure 24. The chemical structures of di- and tri-nuclear organoboron-phosphonium and organoboron-ammonium catalysts[65]

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模块化双功能有机硼氮和硼磷催化体系的设计及其催化转化^★

Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance^★

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模块化双功能有机硼氮和硼磷催化体系的设计及其催化转化★

Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance★

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References 73

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模块化双功能有机硼氮和硼磷催化体系的设计及其催化转化^★

Modular Bifunctional Organoboron-ammonium/phosphonium Catalysts: Design and Catalytic Performance^★