Abstract
Ammonia-borane (AB) is one of the most promising fuel forms for the hydrogen economy, but the reaction requires a good catalyst to accelerate this hydrolysis reaction under ambient conditions. Here, H2 evolution upon hydrolysis of ammonia-borane catalyzed by tetra-(p-hydroxyphenyl) porphyrin (THPP) stabilized transition metal nanoparticles (RhNPs/THPP, RuNPs/THPP, PtNPs/THPP) has been reported for the first time. The as-synthesized nanocomposites (TMNPs/THPP) show high catalytic activity in the AB hydrolysis. Among these TMNPs/THPP, the RhNP-3/THPP exhibits the best catalytic activity with a TOF of 213.64 molH2 molcata−1 min−1. In addition, tandem reaction for 1,1-diphenylethylene hydrogenation has also confirmed the H2 evolution upon hydrolysis of ammonia-borane.
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Li Z, Xu Q (2017) Metal-nanoparticle-catalyzed hydrogen generation from formic acid. Acc Chem Res 50:1449–1458
Chen W, Shen J, Huang Y, Liu X, Astruc D (2020) Catalyzed hydrolysis of tetrahydroxydiboron by graphene quantum dots-stabilized transition metal nanoparticles for hydrogen evolution. ACS Sustain Chem Eng 8:7513–7522
Yang J, Sudik A, Wolverton C, Siegel D (2010) High capacity hydrogen storage materials: attributes for automotive applications and techniques for materials discovery. Chem Soc Rev 39:656–675
Huang Y, Zheng K, Liu X, Meng X, Astruc D (2020) Optimization of Cu catalysts for nitrophenol reduction, click reaction and alkyne coupling. Inorg Chem Front 7:939–945
Yu X, Tang Z, Sun D, Ouyang L, Zhu M (2017) Recent advances and remaining challenges of nanostructured materials for hydrogen storage applications. Prog Mater Sci 88:1–48
Chandra M, Xu Q (2006) A high-performance hydrogen generation system: transition metal-catalyzed dissociation and hydrolysis of ammonia-borane. J Power Sources 156:190–194
She X, Wu J, Zhong J, Xu H, Yang Y, Vajtai R (2016) Oxygenated monolayer carbon nitride for excellent photocatalytic hydrogen evolution and external quantum efficiency. Nano Energy 27:138–146
Khalily M, Eren H, Akbayrak S, Susapto H, Biyikli N, Özkar S (2016) Facile synthesis of three-dimensional Pt-TiO2 nano-networks: a highly active catalyst for the hydrolytic dehydrogenation of ammonia-borane. Angew Chem Int Ed 55:12257–12261
Wang C, Wang Q, Fu F, Astruc D (2020) Hydrogen generation upon nanocatalyzed hydrolysis of hydrogen-rich boron derivatives: recent developments. Acc Chem Res 53:2483–2493
Zhu Q-L, Li J, Xu Q (2013) Immobilizing metal nanoparticles to metal-organic frameworks with size and location control for optimizing catalytic performance. J Am Chem Soc 135:10210–10213
Chen W, Ji J, Feng X, Duan X, Qian G, Li P (2014) Mechanistic insight into size-dependent activity and durability in Pt/CNT catalyzed hydrolytic dehydrogenation of ammonia borane. J Am Chem Soc 136:16736–16739
Guo L, Cai Y, Ge J, Zhang Y, Gong L, Li X (2015) Multifunctional Au–Co@CN nanocatalyst for highly efficient hydrolysis of ammonia borane. ACS Catal 5:388–392
Wang C, Tuninetti J, Wang Z, Zhang C, Ciganda R, Salmon L (2017) Hydrolysis of ammonia-borane over Ni/ZIF-8 nanocatalyst: high efficiency, mechanism, and controlled hydrogen release. J Am Chem Soc 139:11610–11615
Zhan W-W, Zhu Q-L, Xu Q (2016) Dehydrogenation of ammonia borane by metal nanoparticle catalysts. ACS Catal 6:6892–6905
Du C, Ao Q, Cao N, Yang L, Luo W, Cheng G (2015) Facile synthesis of monodisperse ruthenium nanoparticles supported on graphene for hydrogen generation from hydrolysis of ammonia borane. Int J Hydrogen Energy 40:6180–6187
Long Y, Song B, Shi C, Liu W, Gu H (2019) AuNPs composites of gelatin hydrogels crosslinked by ferrocene-containing polymer as recyclable supported catalysts. J Appl Polym Sci 137:48653
Liu F, Liu X, Astruc D, Gu H (2019) Dendronized triazolyl-containing ferrocenyl polymers as stabilizers of gold nanoparticles for recyclable two-phase reduction of 4-nitrophenol. J Colloid Interface Sci 533:161–210
Yang Q, Xu Q, Jiang H (2017) Metal–organic frameworks meet metal nanoparticles: synergistic effect for enhanced catalysis. Chem Soc Rev 46:4774–4808
Navalon S, Dhakshinamoorthy A, Alvaro M, Garcia H (2016) Metal nanoparticles supported on two-dimensional graphenes as heterogeneous catalysts. Coord Chem Rev 312:99–148
Haruta M (2014) Chance and necessity: my encounter with gold catalysts. Angew Chem Int Ed 53:52–56
Amiens C, Ciuculescu-Pradines D, Philippot K (2016) Controlled metal nanostructures: fertile ground for coordination chemists. Coord Chem Rev 308:409–432
Xia Y, Gilroy K, Peng H, Xia X (2017) Seed-mediated growth of colloidal metal nanocrystals. Angew Chem Int Ed 56:60–95
Chechik V, Crooks R (2000) Dendrimer-encapsulated Pd nanoparticles as fluorous phase-soluble catalysts. J Am Chem Soc 122:1243–1244
Wang D, Astruc D (2017) The recent development of efficient earth-abundant transition-metal nanocatalysts. Chem Soc Rev 46:816–854
Liu X, Hamon J-R (2019) Recent developments in penta-, hexa- and heptadentate Schiff base ligands and their metal complexes. Coord Chem Rev 389:94–118
Mu S, Liu W, Zhao L, Long Y, Gu H (2019) Antimicrobial AgNPs composites of gelatin hydrogels crosslinked by ferrocene-containing tetrablock terpolymer. Polymer 169:80–94
Liu X, Mu S, Long Y (2019) Gold nanoparticles stabilized by 1,2,3-triazolyl dendronized polymers as highly efficient nanoreactors for the reduction of 4-nitrophenol. Catal Lett 149:544–551
Zhang T, Yan J, Hu Y, Liu X, Wen L, Zheng K (2019) A simple central seven-membered BOPYIN: synthesis, structural, spectroscopic properties and cellular imaging application. Chem Eur J 25:9266–9271
Zhang N, Zhang T, Liu X, Liu G, Yan J, Zheng K (2019) Speed tunability of the excited-state intramolecular proton transfer process based on seven-membered ring pyrrole-indole H-bond systems. J Mol Liq 286:110887
Li M, Zheng K, Chen H, Liu X, Xiao S, Yan J (2019) A novel 2,5-bis(benzo[d]thiazol-2-yl)phenol scaffold-based ratiometric fluorescent probe for sensing cysteine in aqueous solution and serum. Spectrochim Acta A 217:1–7
Zhou Y, Yan J, Zhang N, Li D, Xiao S, Zheng K (2018) A ratiometric fluorescent probe for formaldehyde in aqueous solution, serum and air using aza-cope reaction. Sens. Actuators B-Chem 258:156–162.
Zhang T, Li Y, Yan J, Liang Y, Xu B, Zheng K (2018) Syntheses and spectroscopic properties of substituted diazaborepins with large stokes shift. Tetrahedron Lett 74:2807–2811
Zhang N, Chen J, Cheng K, Li Y, Wang L, Zheng K (2016) Synthesis and photoelectric property of N-confused porphyrins bearing an ethynylbenzoic and benzoic acid moiety. Res Chem Intermed 43:2921–2929
Li Y, Yan J, Xiao S, Zhang B, Lu F, Cheng K (2016) A novel synthesis of stable 3H-pyrrolizine fused diazaborepin. Tetrahedron Lett 57:3226–3230
Li Y, Yan J, Cheng K, Kong S, Zheng K, Wang L (2017) One-pot synthesis of 5,6-disubstituted 3H-pyrrolizines organocatalyzed by piperidinium acetate. Res Chem Intermed 43:5337–5344
Zhang N, Wen L, Yan J, Liu G, Zhang T, Wang Y (2019) A facile synthesis of seven-membered N, O-ligands and their optical properties. J Mol Struct 1197:714–718
Zhang N, Wen L, Liu X, Chen W, Yan J (2020) One pot synthesis N-confused porphyrin-dipyrrin conjugates and their optical properties. Spectrochim. Acta A. 227:117661
Zhang T, Wen L, Liu G, Yan J, Liu X, Zheng K (2019) A stable AIEgen cis-diarylethene-based ‘ESIPT’ benchmark. Chem Commun 55:13713–13716
Yan J, Liu G, Li N, Zhang N, Liu X (2019) Porphyrin-stabilized transition metal nanoparticles and their applications in the reduction of 4-nitrophenol and the generation of hydroxyl radicals. Eur J Inorg Chem 2019:2806–2810
Hou Z, Dehaen W, Lyskawa J, Woisel P, Hoogenboom R (2017) A supramolecular miktoarm star polymer based on porphyrin metal complexation in water. Chem Commun 53:8423–8426
Wang Q, Fu F, Escobar A, Moya S, Ruiz J, Astruc D (2018) “Click” dendrimer-stabilized nanocatalysts for efficient hydrogen release upon ammonia-borane hydrolysis. ChemCatChem 10:2673–2680
Wang Q, Fu F, Yang S, Martinez M, Ramirez M, Moya S (2019) Dramatic synergy in CoPt nanocatalysts stabilized by “click” dendrimers for evolution of hydrogen from hydrolysis of ammonia borane. ACS Catal 9:1110–1119
Akbayrak S, Tonbul Y, Özkar S (2016) Ceria supported rhodium nanoparticles: superb catalytic activity inhydrogen generation from the hydrolysis of ammonia borane. Appl Catal B 198:162–170
Akbayrak S, Özkar S (2012) Ruthenium(0) nanoparticles supported on multiwalled carbon nanotube as highly active catalyst for hydrogen generation from ammonia-borane. ACS Appl Mater Interfaces 4:6302–6310
Gao Y, Zhang H, Han A, Wang J, Tan H, Tok E, Jaenicke S, Chuah G (2018) Ru/ZrO2 catalysts for transfer hydrogenation of levulinic acid with formic acid/formate mixtures: importance of support stability. Chem Select 3:1343–1351
Li Z, He T, Matsumura D, Miao S, Wu A, Liu L, Wu G, Chen P (2017) Atomically dispersed Pt on the surface of Ni particle: synthesis and catalytic function in hydrogen generation from aqueous ammonia borane. ACS Catal 10:6762–6769
Aijaz A, Karkamkar A, Choi Y, Tsumori N, Rönnebro E, Autrey T, Shioyama H, Xu Q (2012) Immobilizing highly catalytically active Pt nanoparticles inside the pores of metal−organic framework: a double solvents approach. J Am Chem Soc 134:13926–13929
Acknowledgements
Financial support from the National Natural Science Foundation of China (Nos. 21606145, 21805166), the 111 Project (No. D20015), State Key Laboratory of Coordination Chemistry Foundation of Nanjing University (No. SKLCC1811), the Engineering Research Center of Eco-environment in Three Gorges Reservoir Region, Ministry of Education, China Three Gorges University (KF2019-05) and the outstanding young and middle-aged science and technology innovation teams, Ministry of Education, Hubei province, China (T2020004) and China Three Gorges University is gratefully acknowledged.
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Zhang, N., Liu, G., Sun, Y. et al. H2 Evolution Upon Hydrolysis of Ammonia-Borane Catalyzed by Porphyrin Stabilized Nanocatalysts. Catal Lett 151, 2272–2278 (2021). https://doi.org/10.1007/s10562-020-03501-8
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DOI: https://doi.org/10.1007/s10562-020-03501-8