Citation: Yan-Ning CHEN, Jing-Jun LI, Wei-Guang YANG, Shui-Ying GAO. Fabrication and Catalytic Properties of Films Based on Metal Ion-ligand Interaction between K₂PdCl₄ and 3-Amino-3-(4-pyridinyl)-propionitrile[J]. Chinese Journal of Structural Chemistry, ;2020, 39(3): 526-534. doi: 10.14102/j.cnki.0254–5861.2011–2427 shu

Fabrication and Catalytic Properties of Films Based on Metal Ion-ligand Interaction between K₂PdCl₄ and 3-Amino-3-(4-pyridinyl)-propionitrile

Yan-Ning CHEN ^{a, b} ,
Jing-Jun LI ^{a, b} ,
Wei-Guang YANG ^{a, b} ,
Shui-Ying GAO ^b,,

a.
College of Chemistry, Fuzhou University, Fuzhou 350002, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: Shui-Ying GAO, gaosy@fjirsm.ac.cn
Received Date: 24 April 2019
Accepted Date: 4 September 2019

Fund Project: National Key Research and Development Program of China 2017YFA0700100the NSFC 21520102001the NSFC 51572260the NSFC 21571177Strategic Priority Research Program of the Chinese Academy of Sciences XDB20000000Key Research Program of the Chinese Academy of Sciences QYZDJ-SSW-SLH045

Figures(8)

This work presents a highly active and reusable heterogeneous film catalytic assembly for hydrogenation reduction of aromatic nitro compounds. The multilayer structures of PEI-(K₂PdCl₄-P1)_n-ﬁlm (PEI = polyethylenmine, P1 = 3-amino-3-(4-pyridinyl)-propionitrile) bound to quartz slides were fabricated by layer-by-layer (LbL) self-assembly method. Various characterization techniques including X-ray photoelectron spectroscopy (XPS), inductively coupled plasma OES spectrometer (ICP), UV-vis spectroscopy and atomic force microscopy (AFM) were employed to reveal the growth process of the resulting LbL multilayers in detail. Subsequent in situ reduction by H₂ produced Pd nanoparticles embedded in such films were used as catalyst for the hydrogenation of nitroarenes. The catalytic performance test shows that the thin film catalyst can be applied to the hydrogenation reaction of various substituted nitroaromatics, and exhibits good catalytic activity and good catalyst stability. It is worth mentioning that our catalytic films can be easily removed from the reaction system in any time during the reaction, and the catalytic activity could be fully recovered when reused directly in another catalytic cycle for five times.
- palladium,
- hydrogenation,
- nitroarenes,
- layer-by-layer,
- multilayer film
1. [1]
  Fernández, C.; Lujano, E.; Macias, U.; Marcano, J.; Baricelli, P. J.; Longo, C.; Moya, S. A.; Solórzano, M. G.; Ortega, M. C.; Pardey, A. J. Catalytic reduction of 4-nitrobenzoic acid by cis-[Rh(CO)₂(Amine)₂](PF₆) complexes under water-gas shift reaction conditions: kinetics study. Catal. Lett. 2004, 95, 143-150. doi: 10.1023/B:CATL.0000027287.78214.bf
2. [2]
  Dekamin, M. G.; Moghaddam, F. M.; Saeidian, H.; Mallakpour, S. The performance of phthalimide-n-oxyl anion. Monatsh. Chem. 2006, 137, 1591-1595. doi: 10.1007/s00706-006-0553-6
3. [3]
  Arul Dhas, N.; Cohen, H.; Gedanken, A. In situ preparation of amorphous carbon-activated palladium nanoparticles. J. Phys. Chem. B 1997, 101, 6834-6838. doi: 10.1021/jp971308o
4. [4]
  Jagadeesh, R. V.; Surkus, A. E.; Junge, H.; Pohl, M. M.; Radnik, J.; Rabeah, J.; Huan, H.; Schunemann, V.; Bruckner, A.; Beller, M. Nanoscale Fe₂O₃-based catalysts for selective hydrogenation of nitroarenes to anilines. Science 2013, 342, 1073-6. doi: 10.1126/science.1242005
5. [5]
  Nie, R.; Wang, J.; Wang, L.; Qin, Y.; Chen, P.; Hou, Z. Platinum supported on reduced graphene oxide as a catalyst for hydrogenation of nitroarenes. Carbon 2012, 50, 586-596. doi: 10.1016/j.carbon.2011.09.017
6. [6]
  Wienhofer, G.; Sorribes, I.; Boddien, A.; Westerhaus, F.; Junge, K.; Junge, H.; Llusar, R.; Beller, M. General and selective iron-catalyzed transfer hydrogenation of nitroarenes without base. J. Am. Chem. Soc. 2011, 133, 12875-12879. doi: 10.1021/ja2061038
7. [7]
  Yang, X.; Zhao, H.; Gao, S. Layer-by-layer self-assembly of Pd films and their catalytic properties toward nitroarenes hydrogenation. Ind. Eng. Chem. Res. 2017, 56, 3429-3435. doi: 10.1021/acs.iecr.6b04985
8. [8]
  Zapf, A.; Beller, M. Fine chemical synthesis with homogeneous palladium catalysts: examples, status and trends. Top. Catal. 2002, 19, 101-109. doi: 10.1023/A:1013889401432
9. [9]
  Cole-Hamilton, D. J. Homogeneous catalysis--new approaches to catalyst separation, recovery, and recycling. Science 2003, 299, 1702-6. doi: 10.1126/science.1081881
10. [10]
  Jessop, P. G.; Ikariya, T.; Noyori, R. Homogeneous catalysis in supercritical fluids. Chem. Rev. 1999, 99, 475-494. doi: 10.1021/cr970037a
11. [11]
  Larhed, M.; Moberg, C.; Hallberg, A. Microwave-accelerated homogeneous catalysis in organic chemistry. Accounts Chem. Res. 2002, 35, 717-727. doi: 10.1021/ar010074v
12. [12]
  Liu, T. T.; Lin, Z. J.; Shi, P. C.; Ma, T.; Huang, Y. B.; Cao, R. A metallosalen-based porous organic polymer for olefin epoxidation. ChemCatChem. 2015, 7, 2340-2345. doi: 10.1002/cctc.201500374
13. [13]
  Chen, Y.; Kanan, M. W. Tin oxide dependence of the CO₂ reduction efficiency on tin electrodes and enhanced activity for tin/tin oxide thin-film catalysts. J. Am. Chem. Soc. 2012, 134, 1986-9. doi: 10.1021/ja2108799
14. [14]
  van der Vliet, D.; Wang, C.; Debe, M.; Atanasoski, R.; Markovic, N. M.; Stamenkovic, V. R. Platinum-alloy nanostructured thin film catalysts for the oxygen reduction reaction. Electrochimica Acta 2011, 56, 8695-8699. doi: 10.1016/j.electacta.2011.07.063
15. [15]
  Patel, N.; Patton, B.; Zanchetta, C.; Fernandes, R.; Guella, G.; Kale, A.; Miotello, A. Pd-C powder and thin film catalysts for hydrogen production by hydrolysis of sodium borohydride. Int. J. Hydrogen Energy 2008, 33, 287-292. doi: 10.1016/j.ijhydene.2007.07.018
16. [16]
  Cao, G.; Hong, H. G.; Mallouk, T. E. Layered metal phosphates and phosphonates: from crystals to monolayers. Accounts Chem. Res. 2002, 25, 420-427.
17. [17]
  Luthra, S. Homogeneous phase transfer catalyst recovery and re-use using solvent resistant membranes. J Membrane. Sci. 2002, 201, 65-75. doi: 10.1016/S0376-7388(01)00704-9
18. [18]
  Li, J.; Srivastava, S.; Ok, J. G.; Zhang, Y.; Bedewy, M.; Kotov, N. A.; Hart, A. J. Multidirectional hierarchical nanocomposites made by carbon nanotube growth within layer-by-layer-assembled films. Chem. Mater. 2011, 23, 1023-1031. doi: 10.1021/cm1030443
19. [19]
  Ansell, M. A.; Cogan, E. B.; Page, C. J. Coordinate covalent cobalt-diisocyanide multilayer thin films grown one molecular layer at a time. Langmuir 2000, 16, 1172-1179. doi: 10.1021/la990180u
20. [20]
  Song, I. K.; Lee, W. Y. Heteropolyacid (HPA)-polymer composite films as heterogeneous catalysts and catalytic membranes. Appl. Catal. A-Gen. 2003, 256, 77-98. doi: 10.1016/S0926-860X(03)00390-9
21. [21]
  Hod, I.; Sampson, M. D.; Deria, P.; Kubiak, C. P.; Farha, O. K.; Hupp, J. T. Fe-porphyrin-based metal-organic framework films as high-surface concentration, heterogeneous catalysts for electrochemical reduction of CO₂. ACS Catal. 2015, 5, 6302-6309. doi: 10.1021/acscatal.5b01767
22. [22]
  Ren, Z.; Wang, H. L.; Cai, Y. Q.; Chen, M.; Qian, D. J. Construction of Pd(Ⅱ)-poly(4-vinylpyridine) multilayers on quartz substrate surface as heterogeneous catalyst for selective hydrogenation of aromatic conjugated alkenes. Mater. Chem. Phys. 2011, 127, 310-315. doi: 10.1016/j.matchemphys.2011.02.011
23. [23]
  Crespo-Biel, O.; Dordi, B.; Reinhoudt, D. N.; Huskens, J. Supramolecular layer-by-layer assembly: alternating adsorptions of guest-and host-functionalized molecules and particles using multivalent supramolecular interactions. J. Am. Chem. Soc. 2005, 127, 7594-600. doi: 10.1021/ja051093t
24. [24]
  Panella, B.; Vargas, A.; Baiker, A. Magnetically separable Pt catalyst for asymmetric hydrogenation. Journal of Catalysis 2009, 261, 88-93. doi: 10.1016/j.jcat.2008.11.002
25. [25]
  Zhao, M.; Crooks, R. M. Homogeneous hydrogenation catalysis with monodisperse, dendrimer-encapsulated Pd and Pt nanoparticles. Angew. Chem. Int. Edit. 1999, 38, 364-366. doi: 10.1002/(SICI)1521-3773(19990201)38:3<364::AID-ANIE364>3.0.CO;2-L
26. [26]
  Mandal, S.; Roy, D.; Chaudhari, R. V.; Sastry, M. Pt and Pd nanoparticles immobilized on amine-functionalized zeolite: excellent catalysts for hydrogenation and heck reactions. Chem. Mater. 2004, 16, 3714-3724. doi: 10.1021/cm0352504
27. [27]
  Guin, D.; Baruwati, B.; Manorama, S. V. Pd on amine-terminated ferrite nanoparticles: a complete magnetically recoverable facile catalyst for hydrogenation reactions. Org. Lett. 2007, 9, 1419-21. doi: 10.1021/ol070290p
28. [28]
  Wang, Y.; Yao, J.; Li, H.; Su, D.; Antonietti, M. Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media. J. Am. Chem. Soc. 2011, 133, 2362-5. doi: 10.1021/ja109856y
29. [29]
  Gao, S.; Cao, M.; Li, W.; Cao, R. Palladium nanoparticles in situ generated in metal-organic films for catalytic applications. J. Mater. Chem. A 2014, 2, 12185-12193. doi: 10.1039/C4TA01592D
30. [30]
  Chhiba, V.; Bode, M. L.; Mathiba, K.; Kwezi, W.; Brady, D. Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870. J. Mol. Catal. B: Enzym. 2012, 76, 68-74. doi: 10.1016/j.molcatb.2011.12.005
31. [31]
  Lakshmi, K. M.; Parsharamulu, T.; Manorama, S. V.; Lakshmi, K. M.; Parsharamulu, T.; Manorama, S. V. Layered double hydroxides supported nano palladium: an efficient catalyst for the chemoselective hydrogenation of olefinic bonds. J. Mol. Catal. A: Chem. 2012, 365, 115-119. doi: 10.1016/j.molcata.2012.08.017
32. [32]
  Park, J.; Won, S. W.; Mao, J.; Kwak, I. S.; Yun, Y. S. Recovery of Pd(Ⅱ) from hydrochloric solution using polyallylamine hydrochloride-modified Escherichia coli biomass. J. Hazard. Mater. 2010, 181, 794-800. doi: 10.1016/j.jhazmat.2010.05.083
33. [33]
  Shams-nateri, A. Scattering behavior of nonabsorbing metallic nanoparticles. Opt. Laser Technol. 2012, 44, 1670-1674. doi: 10.1016/j.optlastec.2012.01.013
34. [34]
  Son, S. U.; Jang, Y.; Yoon, K. Y.; Kang, E.; Hyeon, T. Facile synthesis of various phosphine-stabilized monodisperse palladium nanoparticles through the understanding of coordination chemistry of the nanoparticles. Nano. Lett. 2004, 4, 1147-1151. doi: 10.1021/nl049519+
1. [1]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
2. [2]
  Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
3. [3]
  Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoS_x assembled from [Mo₃S₁₃]^2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
4. [4]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
5. [5]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
6. [6]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
7. [7]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
8. [8]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
9. [9]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
10. [10]
  Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051
11. [11]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
12. [12]
  Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
13. [13]
  Yanrui Liu , Paramaguru Ganesan , Peng Gao . Harnessing d-f transition rare earth complexes for single layer white organic light emitting diodes. Chinese Journal of Structural Chemistry, 2024, 43(9): 100369-100369. doi: 10.1016/j.cjsc.2024.100369
14. [14]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
15. [15]
  Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
16. [16]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
17. [17]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
18. [18]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
19. [19]
  Shuo Zhang , Haitao Liao , Zhi-Qun Liu , Chong Yan , Jia-Qi Huang . Re-evaluating the nano-sized inorganic protective layer on Cu current collector for anode free lithium metal batteries. Chinese Chemical Letters, 2024, 35(7): 109284-. doi: 10.1016/j.cclet.2023.109284
20. [20]
  Yuhuan Meng , Long Zhang , Lequan Wang , Junming Kang , Hongbin Lu . 20 nm-ultra-thin fluorosiloxane interphase layer enables dendrite-free, fast-charging, and flexible aqueous zinc metal batteries. Chinese Chemical Letters, 2024, 35(12): 110025-. doi: 10.1016/j.cclet.2024.110025

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(300)
HTML views(6)

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

Fabrication and Catalytic Properties of Films Based on Metal Ion-ligand Interaction between K2PdCl4 and 3-Amino-3-(4-pyridinyl)-propionitrile

Metrics

通讯作者: 陈斌, bchen63@163.com

Fabrication and Catalytic Properties of Films Based on Metal Ion-ligand Interaction between K₂PdCl₄ and 3-Amino-3-(4-pyridinyl)-propionitrile