仿生材料聚多巴胺在有机转化中的应用进展

doi:10.6023/cjoc202502024

摘要/Abstract

聚多巴胺(PDA)作为“贻贝激发”的仿生材料, 具有无毒环保和稳定可回收等优势, 在催化领域拥有巨大应用潜力. 聚多巴胺分子包含大量儿茶酚结构, 可以将贵金属离子还原, 其广泛存在的邻二酚/邻醌结构也可以与廉价金属离子配位, 因此, 聚多巴胺能够负载金属构成异相催化剂(M@PDA). 同时, PDA结构中的酚羟基与氨基基团具有酸性和碱性作用, 其自身也可以作为催化剂使用. 综述了M@PDA与PDA在多种有机转化中的应用, 对催化效率和催化剂的循环次数进行了详细描述, 并指出该领域面临的问题与挑战, 期望为聚多巴胺材料在异相催化领域未来的发展提供有益指导.

关键词: 催化剂, 催化剂载体, 有机化合物, 聚多巴胺, 异相催化

Polydopamine (PDA), as a “mussel-inspired” biomimetic material, has great application potential in the field of catalysis because of its non-toxic, environmentally friendly, stable and recyclable advantages. PDA contains a large number of catechol structures, which can reduce noble metal ions. Its widespread o-diphenol/o-quinone structure can also coordinate with cheap metal ions. Therefore, PDA can support metal to form heterogeneous catalysts. Meanwhile, the phenolic hydroxyl groups and amino groups contained in the PDA structure have acidic and basic effects, and they can also be used as catalysts. The application of M@PDA and PDA in a variety of organic transformations is reviewed, describing the catalytic efficiency and the number of cycles of the catalysts in detail. Moreover, the problems and challenges in this field are pointed out, which is expected to provide useful guidance for the future development of polydopamine materials in the field of heterogeneous catalysis.

Key words: catalyst, catalyst support, organic compound, polydopamine, heterogeneous catalysis

引用此文

杨威, 王兵兵, 徐小惠, 孙钟, 唐翠曼, 刘佳琦. 仿生材料聚多巴胺在有机转化中的应用进展[J]. 有机化学, 2025, 45(9): 3314-3325.

Wei Yang, Bingbing Wang, Xiaohui Xu, Zhong Sun, Cuiman Tang, Jiaqi Liu. Recent Progress in the Application of Biomimetic Material Polydopamine in Organic Conversion[J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3314-3325.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 20

图1. PDA的合成与主要结构

Figure 1. Synthesis and main structures of PDA

图2. M@PDA催化剂的结构

Figure 2. Structure of the catalyst M@PDA

图式1. Pd@PDA-CL催化的Suzuki-Miyaura偶联反应[21]

Scheme 1. Suzuki-Miyaura coupling reactions catalyzed by Pd@PDA-CL[21]

图式2. 光照及PDA在催化偶联反应中的作用[21]

Scheme 2. Effects of light and PDA in the catalytic coupling reactions[21]

图式3. Pd/Fe3O4@PDA催化的Suzuki-Miyaura偶联反应及几种重要的沙坦类药物分子结构[55]

Scheme 3. Pd/Fe3O4@PDA catalyzed Suzuki-Miyaura coupling reactions and the structures of Sartans[55]

图式4. Heck偶联及串联的Heck偶联-催化转移加氢反应[57]

Scheme 4. Heck coupling and tandem Heck coupling-catalytic transfer hydrogenation reactions[57]

图式5. Pd/PDA催化的Suzuki偶联反应和串联的Suzuki偶联-催化转移加氢反应[58]

Scheme 5. Suzuki coupling reactions and tandem Suzuki-CTH reactions catalyzed by Pd/PDA[58]

图式6. 不同Pd催化剂催化的Suzuki-Miyaura偶联反应效率[58]

Scheme 6. Efficiency of Suzuki-Miyaura coupling reaction catalyzed by different Pd catalysts[58]

图式7. Pd催化的“非循环”体系下的Heck偶联反应[61]

Scheme 7. Pd catalyzed Heck coupling reaction in a“recycling-free”system[61]

图式8. Pd/Fe3O4@PDA催化的Ullmann偶联反应[62]

Scheme 8. Ullmann coupling reactions catalyzed by Pd/Fe3O4@PDA[62]

图式9. Fe3O4@PDA/Pd(II)催化的Buchwald-Hartwig偶联反应[63]

Scheme 9. Fe3O4@PDA/Pd(II) catalyzed Buchwald-Hartwig coupling reactions[63]

图式10. Pd-PDA催化的硝基和羰基化合物的加氢反应[57]

Scheme 10. Pd-PDA catalyzed hydrogenation of nitro and carbonyl compounds[57]

图式11. Pd-PDA催化的羰基及双键的还原反应[45]

Scheme 11. Reduction of carbonyl group and double bond catalyzed by Pd-PDA[45]

图式12. Ag-PDA催化的对硝基苯酚的还原反应[64-65]

Scheme 12. Reduction of p-nitrophenol catalyzed by Ag- PDA[64-65]

图式13. ZSM-5-PDA/Ag催化的串联反应[66]

Scheme 13. ZSM-5-PDA/Ag catalyzed tandem reactions[66]

图式14. 不同体系下由苄胺合成苯并咪唑的催化效率[67]

Scheme 14. Catalytic efficiency of benzimidazole synthesis from benzylamine in different systems[67]

图式15. CuCl2@PDA催化的烯烃的双氧化反应[68]

Scheme 15. CuCl2@PDA catalyzed dioxygenation of alkenes[68]

图式16. PDA催化的Aldol反应[69]

Scheme 16. PDA catalyzed Aldol reactions[69]

图式17. PDA催化的环氧乙烷与二氧化碳合成环状碳酸酯的反应[70]

Scheme 17. PDA catalyzed synthesis of cyclic carbonates from ethylene oxide and carbon dioxide[70]

图式18. PDA催化的硫醇偶联反应[71]

Scheme 18. PDA catalyzed thiol coupling reactions[71]

参考文献 71

[36]	Cao, E.; Duan, W.; Wang, F.; Wang, A.; Zheng, Y. Carbohydr. Polym. 2017, 158, 44.
[37]	Du, L.; Guo, A.; Cai, A. Micro Nano Lett. 2018, 13, 518.
[38]	Zeng, Y.; Liu, W.; Wang, Z.; Singamaneni, S.; Wang, R. Langmuir 2018, 34, 4036. doi: 10.1021/acs.langmuir.8b00509 pmid: 29528233
[39]	Song, Y.; Jiang, H.; Wang, B.; Kong, Y.; Chen, J. ACS Appl. Mater. Interfaces 2018, 10, 1792.
[40]	Das, T. K.; Ganguly, S.; Bhawal, P.; Remanan, S.; Mondal, S.; Das, N. C. Appl. Nanosci. 2018, 8, 173.
[41]	Ma, J. X.; Yang, H.; Li, S.; Ren, R.; Li, J.; Zhang, X.; Ma, J. RSC Adv. 2015, 5, 97520.
[42]	Xi, J.; Xiao, J.; Xiao, F.; Jin, Y.; Dong, Y.; Jing, F.; Wang, S. Sci. Rep. 2016, 6, 21904.
[43]	Liu, Y.; Li, G.; Qin, R.; Chen, D. Langmuir 2016, 32, 13675.
[44]	Chen, S.; Liu, H. Colloids Surf., A 2022, 635, 128038.
[45]	Fu, P.; Xiao, Z.; Liu, Y.; Wang, L.; Zhang, X.; Li, G. ChemistrySelect 2018, 3, 3351.
[46]	Bian, S. W.; Liu, S.; Chang, L. J. J. Mater. Sci. 2016, 51, 3643.
[47]	Li, Y.; Xie, Y.; Wang, Z.; Zang, N.; Carniato, F.; Huang, Y.; Andolina, C. M.; Parent, L. R.; Ditri, T. B.; Walter, E. D.; Botta, M.; Rinehart, J. D.; Gianneschi, N. C. ACS Nano 2016, 10, 10186.
[48]	Ang, J. M.; Du, Y.; Tay, B. Y.; Zhao, C.; Kong, J.; Stubbs, L. P.; Lu, X. Langmuir 2016, 32, 9265.
[49]	Li, H.; Xi, J.; Donaghue, A. G.; Keum, J.; Zhao, Y.; An, K.; McKenzie, E. R.; Ren, F. Sci. Rep. 2020, 10, 10416.
[50]	Wang, Z.; Xie, Y.; Li, Y.; Huang, Y.; Parent, L. R.; Ditri, T.; Zang, N.; Rinehart, J. D.; Gianneschi, N. C. Chem. Mater. 2017, 29, 8195.
[1]	Waite, J. H. Nat. Mater. 2008, 7, 8.
[2]	Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Science 2007, 318, 426.
[3]	Liu, Y.; Ai, K.; Lu, L. Chem. Rev. 2014, 114, 5057.
[4]	Ryu, J. H.; Messersmith, P. B.; Lee, H. ACS Appl. Mater. Interfaces 2018, 10, 7523.
[5]	Schanze, K. S.; Lee, H.; Messersmith, P. B. ACS Appl. Mater. Interfaces 2018, 10, 7521.
[6]	Cui, X.; Yin, Y.; Ma, Z.; Yin, Y.; Guan, Y.; Rong, S.; Gao, J.; Niu, Y.; Li, M. Nano 2015, 10, 1530003.
[7]	Yang, J.; Stuart, M. A. C.; Kamperman, M. Chem. Soc. Rev. 2014, 43, 8271.
[8]	Lynge, M. E.; van der Westen, R.; Postma, A.; Städler, B. Nanoscale 2011, 3, 4916.
[9]	Liu, M.; Zeng, G.; Wang, K.; Wan, Q.; Tao, L.; Zhang, X.; Wei, Y. Nanoscale 2016, 8, 16819.
[51]	Hemmati, S.; Zangeneh, M. M.; Zangeneh, A. Polyhedron 2020, 117, 114327.
[52]	Yeroslavsky, G.; Richman, M.; Dawidowicz, L.; Rahimipour, S. Chem. Commun. 2013, 49, 5721.
[53]	Li, H.; Marshall, T.; Aulin, Y. V.; Thenuwara, A. C.; Zhao, Y.; Borguet, E.; Strongin, D. R.; Ren, F. J. Mater. Sci. 2019, 54, 6393.
[54]	Kunfia, A.; London, G. Synthesis 2019, 51, 2829.
[55]	Dubey, A. V.; Kumar, V. RSC Adv. 2016, 6, 46864.
[56]	dos Santos, B. F.; da Silva, B. A. L.; de Oliveira, A. R.; Sarragiotto, M. H.; Domingues, N. L. C. Synthesis 2021, 53, 933.
[57]	Kunfi, A.; Szabó, V.; Mastalir, Á.; Bucsi, I.; Mohai, M.; Németh, P.; Bertóti, I.; London, G. ChemCatChem 2017, 9, 3236.
[58]	Kunfi, A.; May, Z.; Németh, P.; London, G. J. Catal. 2018, 361, 84.
[10]	Solano, F. Int. J. Mol. Sci. 2017, 18, 1561.
[11]	Batul, R.; Tamanna, T.; Khaliq, A.; Yu, A. Biomater. Sci. 2017, 5, 1204.
[12]	Wang, B.; Wang, G.; Zhao, B.; Chen, J.; Zhang, X.; Tang, R. Chem. Sci. 2014, 5, 3463.
[13]	Dreyer, D. R.; Miller, D. J.; Freeman, B. D.; Paul, D. R.; Bielawski, C. W. Langmuir 2012, 28, 6428.
[14]	Liebscher, J.; Mrówczynski, R.; Scheidt, H. A.; Filip, C.; Hădade, N. D.; Turcu, R.; Bende, A.; Beck, S. Langmuir 2013, 29, 10539. doi: 10.1021/la4020288 pmid: 23875692
[15]	Hong, S.; Na, Y. S.; Choi, S.; Song, I. T.; Kim, W. Y.; Lee, H. Adv. Funct. Mater. 2012, 22, 4711.
[16]	Ding, Y.; Weng, L. T.; Yang, M.; Yang, Z.; Lu, X.; Huang, N.; Leng, Y. Langmuir 2014, 30, 12258.
[17]	Cîrcu, M.; Filip, C. Polym. Chem. 2018, 9, 3379.
[59]	Ma, R.; Yang, P.; Ma, Y.; Bian, F. ChemCatChem 2018, 10, 1446.
[60]	Farzad, E.; Veisi, H. J. Ind. Eng. Chem. 2018, 60, 114.
[61]	Fei, X.; Kong, W.; Chen, X.; Jiang, X.; Shao, Z.; Lee, J. Y. ACS Catal. 2017, 7, 2412.
[62]	Dubey, A. V.; Kumar, A. V. Appl. Organomet. Chem. 2020, 34, e5570.
[63]	Veisi, H.; Sarachegol, P.; Hemmati, S. Polyhedron 2018, 156, 64.
[64]	Zhang, L.; Liu, Z.; Wang, Y.; Xie, R.; Ju, X.-J.; Wang, W.; Lin, L.-G.; Chu, L.-Y. Chem. Eng. J. 2017, 309, 691.
[65]	Wang, K.; Zhu, X.; Yang, Y.; Ye, D.; Chen, R.; Liao, Q. J. Environ. Chem. Eng. 2022, 10, 108253.
[66]	GhavamiNejad, A.; Kalantarifard, A.; Yang, G. S.; Kim, C. S. Microporous Mesoporous Mater. 2016, 225, 296.
[18]	Chen, C. T.; Martin-Martinez, F. J.; Jung, G. S.; Buehler, M. J. Chem. Sci. 2017, 8, 1631.
[19]	Liebscher, J. Eur. J. Org. Chem. 2019, 2019, 4976. doi: 10.1002/ejoc.201900445
[20]	Molnár, A. ChemCatChem 2020, 12, 2649.
[21]	Xie, A.; Zhang, K.; Wu, F.; Wang, N.; Wang, Y.; Wang, M. Catal. Sci. Technol. 2016, 6, 1764.
[22]	Zeng, T.; Zhang, X.; Niu, H.; Li, W.; Cai, Y. App. Catal. B 2013, 134-135, 26.
[23]	Liu, R.; Guo, Y.; Odusote, G.; Qu, F.; Priestley, R. D. ACS Appl. Mater. Interfaces 2013, 5, 9167.
[24]	Luo, J.; Zhang, N.; Liu, R.; Liu, X. RSC Adv. 2014, 4, 64816.
[25]	Kim, I.; Son, H. Y.; Yang, M. Y.; Nam, Y. S. ACS Appl. Mater. Interfaces 2015, 7, 14415.
[26]	Cao, J.; Mei, S.; Jia, H.; Ott, A.; Ballauff, M.; Lu, Y. Langmuir 2015, 31, 9483.
[27]	Zhao, Y.; Yeh, Y.; Liu, R.; You, Y.; Qu, F. Solid State Sci. 2015, 45, 9.
[28]	Ni, Y.; Tong, G.; Wang, J.; Li, H.; Chen, F.; Yu, C.; Zhou, Y. RSC Adv. 2016, 6, 40698.
[29]	Wei, Q.; Shi, R.; Lu, D.; Lei, Z. RSC Adv. 2016, 6, 29245.
[30]	Wu, Z.; Lin, H.; Wang, Y.; Yu, X.; Li, J.; Xiong, Z.; Wang, Y.; Huang, Y.; Chen, T.; Liu, F. RSC Adv. 2016, 6, 62302.
[31]	Yu, J.; Lu, S.; Xu, W.; He, G.; He, D. Appl. Organomet. Chem. 2017, 31, e3785.
[32]	Zhang, J.; Fang, Q.; Duan, J.; Xu, H.; Xu, H.; Xuan, S. Langmuir 2018, 34, 4298.
[33]	Zeng, Z.; Wen, M.; Yu, B.; Ye, G.; Huo, X.; Lu, Y.; Chen, J. ACS Appl. Mater. Interfaces 2018, 10, 14735.
[34]	Choi, G. H.; Rhee, D. K.; Park, A. R.; Oh, M. J.; Hong, S.; Richardson, J. J.; Guo, J.; Caruso, F.; Yoo, P. J. ACS Appl. Mater. Interfaces 2016, 8, 3250.
[35]	Lu, S.; Yu, J.; Cheng, Y.; Wang, Q.; Barras, A.; Xu, W.; Szunerits, S.; Cornu, D.; Boukherroub, R. Appl. Surf. Sci. 2017, 411, 163.
[67]	Badbedast, M.; Khalili, D.; Abdolmaleki, A.; Norouzi, F. Appl. Organomet. Chem. 2023, 37, e7197.
[68]	Yang, W.; Liu, J.; Wang, B.; Xu, X.; Sun, Z. Sustainable Chem. Pharm. 2024, 40, 101652.
[69]	Mrowczynski, R.; Bunge, A.; Liebscher, J. Chem.-Eur. J. 2014, 20, 8647.
[70]	Yang, Z.; Sun, J.; Liu, X.; Su, Q.; Liu, Y.; Li, Q.; Zhang, S. Tetrahedron Lett. 2014, 55, 3239.
[71]	Du, Y.; Yang, H.-C.; Xu, X.-L.; Wu, J.; Xu, Z.-K. ChemCatChem 2015, 7, 3822.