AI Chat Paper
Note: Please note that the following content is generated by AMiner AI. SciOpen does not take any responsibility related to this content.
{{lang === 'zh_CN' ? '文章概述' : 'Summary'}}
{{lang === 'en_US' ? '中' : 'Eng'}}
Chat more with AI
Powered by AMiner. Clicking this button will take you away from SciOpen.
Home Paper and Biomaterials Article
PDF (870.6 KB)
Cite
EndNote(RIS) BibTeX
Collect
Submit Manuscript AI Chat Paper
Show Outline
Outline
Show full outline
Hide outline
Outline
Show full outline
Hide outline
Original Article | Open Access

Polyoxometalate-loaded Nanocellulose Sponge as a Novel Catalyst for the Regioselective Hydroboration of Phenylacetylene

GuoQing Yang1, CongCong Zhang1, BiJia Wang1,2( ), ZhiPing Mao1,2, Hong Xu1,2, Yi Zhong1,2, XueLing Feng1,2, XiaoFeng Sui1,2( )
Key Lab of Science and Technology of Eco-textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, China
Innovation Center for Textile Science and Technology of DHU, Donghua University, Shanghai, 201620, China
Show Author Information

Abstract

In this work, an amino-modified cellulose nanofiber sponge was prepared and used as a support for polyoxometalate (POM) catalysts with a high loading efficiency. Fourier transform infrared spectroscopy, thermogravimetric analysis, and energy-dispersive X-ray spectroscopy revealed that an Anderson-type POM, (NH4)4[CuMo6O18(OH)6]·5H2O was successfully immobilized on the sponge based on electrostatic interactions. Morphological analysis indicated that the POM-loaded sponge retained its porous structure and that the POM was homogeneously distributed on the sponge walls. The POM-loaded sponge exhibited excellent mechanical properties by recovering 79.9% of its original thickness following a 60% compression strain. The POM-loaded sponge was found to effectively catalyze the hydroboration of phenylacetylenes, yielding excellent conversion and regioselectivity of up to 96% and 99%, respectively. Its catalytic activity remained unchanged after five reuse cycles. These findings represent a scalable strategy for immobilizing POMs on porous supports.

Keywords

heterogeneous catalystpolyoxometalatescellulose nanofibercatalyst immobilizationhydroboration

References

[1]

Gamelas J A F, Evtyugina M G, Portugal I, et al. New polyoxometalate-functionalized cellulosic fibre/silica hybrids for environmental applications[J]. RSC Advances, 2012, 2(3): 831-839.
Crossref Google Scholar
[2]

Ji Y, Ma Y, Ma Y, et al. Water decontamination by polyoxometalate-functionalized 3D-printed hierarchical porous devices[J]. Chemical Communications, 2018, 54(24): 3018-3021.
Crossref Google Scholar
[3]

Sven H, Laura D M, Jesus M D L F, et al. Removal of multiple contaminants from water by polyoxometalate supported ionic liquid phases (POM-SILPs)[J]. Angewandte Chemie International Edition, 2017, 56(6): 1667-1670.
Crossref Google Scholar
[4]

Gamelas J A F, Oliveira F, Evtyugina M G, et al. Catalytic oxidation of formaldehyde by ruthenium multisubstituted tungstosilicic polyoxometalate supported on cellulose/silica hybrid[J]. Applied Catalysis A: General, 2015, DOI: 10.1016/j.apcata.2015.10.003.
Crossref Google Scholar
[5]

Yuan Y, Li G Z, Ding Y H, et al. Preparation of keggin-type polyoxometallate/polypyrrole composite microtubes and their assist-catalytic properties towards methanol oxidation[J]. Chem Electro Chem, 2018, 5(6): 964-967.
Crossref Google Scholar
[6]

Wu H, Yang H K, Wang W. Cova l ent ly-l inked polyoxometalate-polymer hybrids: optimizing synthesis, appealing structures and prospective applications[J]. New Journal of Chemistry, 2016, 40(2): 886-897.
Crossref Google Scholar
[7]

Chen L, Chen W L, Wang X L, et al. Polyoxometalates in dye-sensitized solar cells[J]. Chemical Society Reviews, 2019, 48(1): 260-284.
Crossref Google Scholar
[8]

Romanenko I, Lechner M, Wendler F, et al. POMbranes: polyoxometalate-functionalized block copolymer membranes for oxidation catalysis[J]. Journal of Materials Chemistry A, 2017, 5(30): 15789-15796.
Crossref Google Scholar
[9]

Chen Q, Goshorn D P, Scholes C P, et al. Coordination compounds of polyoxovanadates with a hexametalate core. Chemical and structural characterization of [VⅤ6O13[(OCH2)3CR]2]2-, [VⅤ6O11(OH)2[(OCH2)3CR]2], [VⅣ4VⅤ2O9(OH)4[(OCH2)3CR]2]2-, and [VⅣ6O7(OH)6](OCH2)3CR]2]2-[J]. Journal of the American Chemical Society, 1992, 114(12): 4667-4681.
Crossref Google Scholar
[10]

Sebulsky R T, Henke A M. Alkylation of benzene with dodecene-1 catalyzed by supported silicotungstic acid[J]. Industrial & Engineering Chemistry Process Design and Development, 1971, 10(2): 272-279.
Crossref Google Scholar
[11]

Izumi Y, Urabe K. Catalysis of heteropoly acids entrapped in activated carbon[J]. Chemistry Letters, 1981, 10(5): 663-666.
Crossref Google Scholar
[12]

Wei Y, Xu B, Barnes C L, et al. An efficient and convenient reaction protocol to organoimido derivatives of polyoxometalates[J]. Journal of the American Chemical Society, 2001, 123(17): 4083-4084.
Crossref Google Scholar
[13]

Hu J, Ji Y, Chen W, et al. "Wiring" redox-active polyoxometalates to carbon nanotubes using a sonication-driven periodic functionalization strategy[J]. Energy & Environmental Science, 2016, 9(3): 1095-1101.
Crossref Google Scholar
[14]

Herrmann S, Ritchie C, Streb C. Polyoxometalate-conductive polymer composites for energy conversion, energy storage and nanostructured sensors[J]. Dalton Trans, 2015, 44(16): 7092-7104.
Crossref Google Scholar
[15]

Panchenko V N, BORBÁTH I, TIMOFEEVA M N, et al. Amine-modified silica NH2—(CH2)x—SiO2 (x=0, 2, 3) as support for cobalt-substituted polyoxometalate TBA4HPW11CoO39: Effect of the nature of the support on the oxidation activity[J]. Journal of Molecular Catalysis A: Chemical, 2010, 319(1): 119-125.
Crossref Google Scholar
[16]

Wang L, Xu X, Feng Z, et al. WO3-x based composite material with chitosan derived nitrogen doped mesoporous carbon as matrix for oxygen vacancy induced organic pollutants catalytic reduction and IR driven H2 production[J]. Journal of Solid State Chemistry, 2018, 266: 23-30.
Crossref Google Scholar
[17]

Zhang Z, Zhao W, Ma B, et al. The epoxidation of olefins catalyzed by a new heterogeneous polyoxometalate-based catalyst with hydrogen peroxide[J]. Catalysis Communications, 2010, 12(4): 318-322.
Crossref Google Scholar
[18]

Rezvani M A, Asli M A N, Oveisi M, et al. An organic-inorganic hybrid based on an Anderson-type polyoxometalate immobilized on PVA as a reusable and efficient nanocatalyst for oxidative desulphurization of gasoline[J]. RSC Advances, 2016, 6(58): 53069-53079.
Crossref Google Scholar
[19]

Xu L, Boring E, Hill C L. Polyoxometalate-modified fabrics: new catalytic materials for low-temperature aerobic oxidation[J]. Journal of Catalysis, 2000, 195(2): 394-405.
Crossref Google Scholar
[20]

Li Y, Xu L, Xu B, et al. Cellulose sponge supported palladium nanoparticles as recyclable cross-coupling catalysts[J]. ACS Appl Mater Interfaces, 2017, 9(20): 17155-17162.
Crossref Google Scholar
[21]

Cheng H, Du Y, Wang B, et al. Flexible cellulose-based thermoelectric sponge towards wearable pressure sensor and energy harvesting[J]. Chem Eng J, 2018, 338: 1-7.
Crossref Google Scholar
[22]

Wu C N, Fuh S C, Lin S P, et al. TEMPO-oxidized Bacterial cellulose pellicle with silver nanoparticles for wound dressing[J]. Biomacromolecules, 2018, 19(2): 544-554.
Crossref Google Scholar
[23]

Sundararajan S, Samui A B, Kulkarni P S. Shape-stabilized poly(ethylene glycol) (PEG)-cellulose acetate blend preparation with superior PEG loading via microwave-assisted blending[J]. Solar Energy, 2017, 144: 32-39.
Crossref Google Scholar
[24]

Zhang C, Zhou M, Liu S, et al. Copper-loaded nanocellulose sponge as a sustainable catalyst for regioselective hydroboration of alkynes[J]. Carbohydrate Polymers, 2018, 191: 17-24.
Crossref Google Scholar
[25]

Liu H, Rong L, Wang B, et al. Facile synthesis of cellulose derivatives based on cellulose acetoacetate[J]. Carbohydrate Polymers, 2017, 170: 117-123.
Crossref Google Scholar
[26]

Lu J, Askeland P, Drzal L T. Surface modification of microfibrillated cellulose for epoxy composite applications[J]. Polymer, 2008, 49(5): 1285-1296.
Crossref Google Scholar
[27]

Zhang Z, Sèbe G, Rentsch D, et al. Ultralightweight and flexible silylated nanocellulose sponges for the selective removal of oil from water[J]. Chemistry of Materials, 2014, 26(8): 2659-2668.
Crossref Google Scholar
[28]

Cheng H, Li Y, Wang B, et al. Chemical crosslinking reinforced flexible cellulose nanofiber-supported cryogel[J]. Cellulose, 2018, 25(1): 573-582.
Crossref Google Scholar
[29]

Gorgas N, Alves L G, Stöger B, et al. Stable, yet highly reactive nonclassical iron(Ⅱ) polyhydride pincer complexes: Z-selective dimerization and hydroboration of terminal alkynes[J]. Journal of the American Chemical Society, 2017, 139(24): 8130-8133.
Crossref Google Scholar
[30]

Obligacion J V, Neely J M, Yazdani A N, et al. Cobalt catalyzed Z-selective hydroboration of terminal alkynes and elucidation of the origin of selectivity[J]. Journal of the American Chemical Society, 2015, 137(18): 5855-5858.
Crossref Google Scholar
[31]

Gunanathan C, Hölscher M, Pan F, et al. Ruthenium catalyzed hydroboration of terminal alkynes to Z-vinylboronates[J]. Journal of the American Chemical Society, 2012, 134(35): 14349-14352.
Crossref Google Scholar
[32]

Wei Y G, Yu H, Zhai Y Y, et al. Transition-metal-controlled inorganic ligand-supported non-precious metal catalysts for the aerobic oxidation of amines to imines[J]. Chemistry-A European Journal, 2017, 23(56): 13883-13887.
Crossref Google Scholar
[33]

Wu PF, Yin P C, Zhang J, et al. Single-side organically functionalized anderson-type polyoxometalates[J]. Chemistry: A European Journal, 2011, 17(43): 12002-12005.
Crossref Google Scholar
[34]

Zhang J, Cheng Y, Tebyetekerwa M, et al. "Stiff-Soft" binary synergistic aerogels with superflexibility and high thermal insulation performance[J]. Advanced Functional Materials, 2019, DOI: 10.1002/adfm.201806407.
Crossref Google Scholar
Paper and Biomaterials
Volume 4 Issue 2,
April 2019
Pages 1-9
DOI: 10.26599/PBM.2019.9260009
Cite this article:
Yang G, Zhang C, Wang B, et al. Polyoxometalate-loaded Nanocellulose Sponge as a Novel Catalyst for the Regioselective Hydroboration of Phenylacetylene. Paper and Biomaterials, 2019, 4(2): 1-9. https://doi.org/10.26599/PBM.2019.9260009

480

Views

12

Downloads

0

Crossref

0

Scopus

Altmetrics
Received: 21 February 2019
Accepted: 19 March 2019
Published: 01 April 2019
© 2019 Paper and Biomaterials Editorial Board

This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/)
Return