Abstract
Magnetic mesoporous silica nanocomposite, Fe3O4-MCM-41, was functionalized with N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAPS) and then condensed with 5,5′-methylene bis(salicylaldehyde), followed by N(4)-phenylthiosemicarbazide to produce a ONS Schiff base grafted nanocomposite. Finally, by adding palladium(II) acetate, the palladium Schiff base complex was immobilized on magnetic nanocomposite. The characterization of new nanocomposites was carried out by means of several techniques such as FT-IR, XRD, FE-SEM, HRTEM, EDS, BET, VSM, XPS, DRS and TGA. The new nanocatalyst, Fe3O4@MCM-41-SB-Pd, was used in synthesis of symmetrical and unsymmetrical biaryl compounds via the Suzuki–Miyaura cross-coupling of phenylboronic acid with aryl halides. This catalyst was easily recovered by applying an external magnetic field and reused for several times without significant loss of its catalytic activity. Also the ability of synthesized mesoporous nanocomposites for enzyme immobilization was investigated and results showed that they efficiently immobilized α-amylase enzyme.
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ALOthman Z (2012) Materials 5:2874
Huang W, Zhang Y, Li D (2017) J Environ Manag 193:470
Cashin VB, Eldridge DS, Yu A, Zhao D (2018) Environ Sci 4:110
Paris JL, Cabañas MV, Manzano M, Vallet-Regí M (2015) ACS Nano 9:11023
Slowing II, Vivero-Escoto JL, Wu C-W, Lin VS-Y (2008) Adv Drug Deliv Rev 60:1278
Hasanzadeh M, Nahar AS, Hassanpour S, Shadjou N, Mokhtarzadeh A, Mohammadi J (2017) Enzyme Microb Technol 105:64
Nabavi ZPS, Åkerman Br (2017) J Phys Chem B 121:2575
Zheng G, Zhao R, Xu A, Shen Z, Chen X, Shao J (2018) Eur J Pharmacol Sci 111:492
Lee C-H, Lin T-S, Mou C-Y (2009) Nano Today 4:165
De Vos DE, Dams M, Sels BF, Jacobs PA (2002) Chem Rev 102:3615
Zucca P, Sanjust E (2014) Molecules 19:14139
Mirante F, Gomes N, Branco LC, Cunha-Silva L, Almeida PL, Pillinger M, Gago S, Granadeiro CM, Balula SS (2019) Microporous Mesoporous Mater 275:163
Sharma N, Ojha H, Bharadwaj A, Pathak DP, Sharma RK (2015) RSC Adv 5:53381
Chiang YD, Dutta S, Chen CT, Huang YT, Lin KS, Wu JC, Suzuki N, Yamauchi Y, Wu KCW (2015) Chemsuschem 8:789
Yang L, Peng C, Fang X, Cheng Z, Zhou Z (2019) Catal Commun 121:68
Nguyen-Huy C, Lee H, Lee J, Kwak JH, An K (2019) Appl Catal A 571:118
Pal N, Bhaumik A (2015) RSC Adv 5:24363
Hu J, Wu Q, Li K, Li W, Ma F, Zhang S, Su F, Guo Y, Wang Y (2010) Catal Commun 12:238
Gawande MB, Monga Y, Zboril R, Sharma R (2015) Coord Chem Rev 288:118
Xie W, Zang X (2016) Food Chem 194:1283
Singh H, Iyengar N, Rajput P, Sinha AK (2019) Mater Res Bull 112:363
Rezaei S, Ghorbani-Choghamarani A, Badri R (2016) Appl Organomet Chem 30:985
Manjunatha K, Koley TS, Kandathil V, Dateer RB, Balakrishna G, Sasidhar B, Patil SA, Patil SA (2018) Appl Organomet Chem 32:e4266
Ghorbani-Choghamarani A, Ghasemi B, Safari Z, Azadi G (2015) Catal Commun 60:70
Azar ARJ, Safaei E, Mohebbi S (2015) Mater Res Bull 70:753
Dhara K, Sarkar K, Srimani D, Saha SK, Chattopadhyay P, Bhaumik A (2010) Dalton Trans 39:6395
Rafiee F, Mehdizadeh N (2018) Catal Lett 1
Jana S, Dutta B, Bera R, Koner S (2008) Inorg Chem 47:5512
Kumari S, Layek S, Pathak DD (2017) New J Chem 41:5595
Tahmasbi L, Sedaghat T, Motamedi H, Kooti M (2018) J Solid State Chem 258:517
Pitzalis F, Monduzzi M, Salis A (2017) Microporous Mesoporous Mater 241:145
Liu LH, Shih YH, Liu WL, Lin CH, Huang HY (2017) Chem Sus Chem 10:1364
Ma X, Sánchez S (2017) Tetrahedron 73:4883
Kumar A, Park GD, Patel SKS, Kondaveeti S, Otari S, Anwar MZ, Kalia VC, Singh Y, Kim SC, Cho B-K, Sohn J-H, Kim DR, Kang YC, Lee J-K (2019) Chem Eng J 359:1252
Liu J, Liu Y, Jin D, Meng M, Jiang Y, Ni L, Liu Z (2019) Solid State Sci 89:15
Cacicedo ML, Manzo RM, Municoy S, Bonazza HL, Islan GA, Desimone M, Bellino M, Mammarella EJ, Castro GR (2019) Chapter 7—immobilized enzymes and their applications. In: Singh RS, Singhania RR, Pandey A, Larroche C (eds) Advances in enzyme technology, 169. Elsevier, New York
Marvel C, Tarköy N (1957) J Am Chem Soc 79:6000
Zhu J, He J, Du X, Lu R, Huang L, Ge X (2011) Appl Surf Sci 257:9056
Kooti M, Afshari M (2012) Mater Res Bull 47:3473
Wang Y, Li B, Zhang L, Li P, Wang L, Zhang J (2011) Langmuir 28:1657
Lei B, Li B, Zhang H, Lu S, Zheng Z, Li W, Wang Y (2006) Adv Funct Mater 16:1883
Deng Y, Qi D, Deng C, Zhang X, Zhao D (2008) J Am Chem Soc 130:28
Wang Y, Li B, Zhang L, Song H (2013) Langmuir 29:1273
Jang J, Lim H (2010) Microchem J 94:148
Wang P, Lu Q, Li J (2010) Mater Res Bull 45:129
Ghorbani-Vaghei R, Hemmati S, Veisi H (2014) J Mol Catal A 393:240
Zhang G, Wang P, Wei X (2013) Catal Lett 143:1188
Baran T (2019) Int J Biol Macromol 127:232
Gogoi N, Bora U, Borah G, Gogoi PK (2017) Appl Organomet Chem 31:e3686
Kunfi A, May Z, Németh P, London G (2018) J Catal 361:84
Yuan L, Chen W, Hu J, Zhang JZ, Yang D (2013) Langmuir 29:734
Yuan L, Tang Q, Yang D, Zhang JZ, Zhang F, Hu J (2011) J Phys Chem C 115:9926
Carniato F, Bisio C, Paul G, Gatti G, Bertinetti L, Coluccia S, Marchese L (2010) J Mater Chem 20:5504
Miyasaka K, Neimark AV, Terasaki O (2008) J Phys Chem C 113:791
Cai Y, Ling L, Li X, Chen M, Su L (2015) J Solid State Chem 226:179
Shen L, Wu Y, Ma W (2015) Spectrochim Acta A 138:348
Zhang D, Wang X, Qiao Z-A, Tang D, Liu Y, Huo Q (2010) J PhysChem C 114:12505
Hajjami M, Ghorbani F, Bakhti F (2014) Appl Catal A 470:303
Tang D, Zhang L, Zhang Y, Qiao Z-A, Liu Y, Huo Q (2012) J Colloid Interface Sci 369:338
Liu C-C, Lin T-S, Chan SI, Mou C-Y (2015) J Catal 322:139
Tukhani M, Panahi F, Khalafi-Nezhad A (2017) ACS Sustain Chem Eng 6:1456
Firuzabadi FD, Asadi Z, Panahi F (2016) RSC Adv 6:101061
Sadhasivam V, Balasaravanan R, Siva A (2019) Appl Organomet Chem e4994
Meng X, Zhang Z (2017) Appl Catal B 209:383
Islam SM, Roy AS, Mondal P, Salam N (2012) Appl Organomet Chem 26:625
Niakan M, Asadi Z, Masteri-Farahani M (2018) Colloids Surf A 551:117
Trivedi M, Singh G, Kumar A, Rath NP (2016) Inorg Chim Acta 449:1
Sun C, Sun K, Tang S (2018) Mater Chem Phys 207:181
Sarmah C, Sahu D, Das P (2012) Catal Today 198:197
Li W, Zhang B, Li X, Zhang H, Zhang Q (2013) Appl Catal A 459:65
Pourjavadi A, Motamedi A, Marvdashti Z, Hosseini SH (2017) Catal Commun 97:27
Veisi H, Najafi S, Hemmati S (2018) Int J Biol Macromol 113:186
Hartmann M, Jung D (2010) J Mater Chem 20:844
Liu W, Wang L, Jiang R (2012) Top Catal 55:1146
Sheldon RA (2007) Adv Synth Catal 349:1289
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Support of this work by Shahid Chamran University of Ahvaz, Iran (Grant No. 1397) is gratefully acknowledged.
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Ahmadi, A., Sedaghat, T., Azadi, R. et al. Magnetic Mesoporous Silica Nanocomposite Functionalized with Palladium Schiff Base Complex: Synthesis, Characterization, Catalytic Efficacy in the Suzuki–Miyaura Reaction and α-Amylase Immobilization. Catal Lett 150, 112–126 (2020). https://doi.org/10.1007/s10562-019-02913-5
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DOI: https://doi.org/10.1007/s10562-019-02913-5