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★

doi:10.6023/A23050206

化学学报 ›› 2023, Vol. 81 ›› Issue (11): 1551-1565.DOI: 10.6023/A23050206 上一篇下一篇

所属专题：庆祝《化学学报》创刊90周年合辑

综述

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)

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摘要/Abstract

有机硼化合物是近年来广泛研究的一类非金属催化剂, 其在环氧烷烃参与的开环均聚合和共聚合方面展现了良好的适用性, 但二元亲电亲核双组分催化体系在加入大量的反应单体后由于稀释效应带来的熵不利因素往往导致活性减小或失活的问题, 同时也难以制备大分子量的聚合物材料. 基于此, 本文主要综述了本课题组设计的分子内同时含有亲电和亲核中心的双功能有机硼-季铵盐和有机硼-季鏻盐催化体系的研究进展, 重点梳理了此类双功能有机硼催化剂的设计脉络和设计原则, 对比了双功能和双组分有机硼催化体系之间的聚合反应机理, 总结了利用双功能有机硼催化剂在环氧烷烃开环聚合制备脂肪族聚醚、环氧烷烃和二氧化碳共聚合制备二氧化碳基聚碳酸酯、环氧烷烃和环状酸酐共聚合制备聚酯等方面的内容, 展望了有机硼催化剂在高分子合成化学方向的未来和趋势.

关键词: 有机硼, 路易斯酸碱对, 开环聚合, 二氧化碳, 催化剂

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

引用此文

杨贯文, 伍广朋. 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^★[J]. 化学学报, 2023, 81(11): 1551-1565.

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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图/表 24

图1. 本文作者参与研究的用于二氧化碳和环氧烷烃共聚合的双组分和双功能四齿席夫碱钴配合物催化体系[17-18]

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]

图2. 2016年Gnanou、Feng、Hadjichristidis等报道的三乙基硼烷/鎓盐双组分催化体系及其催化环氧烷烃与二氧化碳共聚合机理[19]

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]

图3. 我们报道的(a)动态路易斯酸碱有机硼氮和硼磷多核催化体系设计策略, (b)以季铵化(季鏻化)和硼氢化两步制备双功能有机硼催化剂, (c)代表性的单核、双核、三核与四核双功能有机硼氮和硼磷催化剂. 其中, A表示氮原子或磷原子; B为硼原子; X为卤素或其他酸根离子[25-26]

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]

图4. 用于环氧环己烷与二氧化碳共聚的单核硼双功能催化剂[27]

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

图5. (a)双组分催化体系8/BTEAB和双功能催化剂3b, (b)双组分催化体系8/BTEAB和双功能催化剂3b在不同投料量下的催化性能[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]

图6. 硼烷8, 双组分8/BTEAB体系(物质的量比为1/1)和双功能有机硼氮催化剂3b的核磁硼谱[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]

图7. 密度泛函理论计算模拟出的催化剂3b的稳定结构[27]

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

图8. 单核双功能有机硼氮催化剂催化的CHO与CO2共聚合反应机理[27]

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

图9. 催化剂9及其与CHO反应中间体的核磁硼谱[28]

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

图10. 单核有机硼催化剂催化β-丁内酯开环聚合机理[34]

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

图11. 用于环氧烷烃与CO2开环共聚合的单核有机硼催化剂10[37]

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

图12. 用于环氧烷烃开环聚合的双核有机硼催化剂11~13[49]

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

图13. (a)双功能催化剂、双组分对比催化剂及其催化PO开环均聚合活性, (b)核磁硼谱研究[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]

图14. 基于双功能有机硼催化剂调控的PO开环聚合提出的分子内铵阳离子辅助的链穿梭聚合机理[49]

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

图15. 双核有机硼催化剂结构优化[36]

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

图16. (a) CO2/PO共聚物可能的-ABB-单元结构, (b)聚合物水解-衍生化实验以及得到的化合物晶体结构[52] (a) CO2/PO共聚物可能的-ABB-单元结构, (b)聚合物水解-衍生化实验以及得到的化合物晶体结构[52]

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]

图17. (a) 23?2DMF、12?2DMF、24?2DMF和25?2DMF的晶体结构, (b) B…B距离(d)与B—N+—B夹角(θ)的线性关系, (c)聚合物结构单元选择性与B—N+—B夹角(θ)的线性关系[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]

图18. (a) ECH和CO2开环共聚及产物选择性, (b)双功能Salen-Co(III)催化剂, (c)环状碳酸酯的生成路线, (d) Salen-Co(III)催化的聚合反应溶液和纯化后的聚合物照片, (e)四核有机硼催化剂26的化学结构, (f) 26b?4DMF晶体结构, (g) 26催化的聚合反应溶液和纯化后的聚合物照片[59] (a) ECH和CO2开环共聚及产物选择性, (b)双功能Salen-Co(III)催化剂, (c)环状碳酸酯的生成路线, (d) Salen-Co(III)催化的聚合反应溶液和纯化后的聚合物照片, (e)四核有机硼催化剂26的化学结构, (f) 26b?4DMF晶体结构, (g) 26催化的聚合反应溶液和纯化后的聚合物照片[59]

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]

图19. 基于催化剂26调控的ECH和CO2开环共聚提出的分子内循环顺序聚合机理[59]

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

图20. 近期文献报道的多核双功能有机硼催化剂

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

图21. 单核有机硼-季鏻盐与有机硼-季铵盐催化剂催化CHO与PA开环共聚的活性对比[65]

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

图22. DFT计算优化的(a)有机硼-季鏻盐催化剂和(b)有机硼-季铵盐催化剂的结构[65]

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

图23. 埃克森美孚石油公司报道的含鏻盐的单核有机硼催化剂及其催化CHO与CO2共聚的过渡态结构[69]

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]

图24. 双核和三核有机硼-季鏻盐催化剂及有机硼-季铵盐催化剂的化学结构[65]

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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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^★