间苯二酚保护的抗菌Pd纳米粒子催化C-C偶联反应活性

doi:10.1016/S1872-2067(15)61021-X

摘要/Abstract

摘要：

合成了新型四甲氧基间苯二酚-四酰肼(TMRTH), 并作为还原剂和封端剂用于合成水分散性稳定的Pd纳米粒子(PdNPs). 采用紫外-可见光谱、透射电镜、能量散射谱和粉末X射线衍射对所得TMRTH-PdNPs样品进行了表征. 结果表明, 所制纳米粒子具有多分散性, 粒径为5 ± 2 nm, 并在Suzuki-Miyuara交叉偶联反应中可重复使用5次, 具有较高的催化效率. 该纳米催化剂在反应时间、催化剂用量和可重复使用性能等方面优于常规Pd催化剂. 另外, TMRTH-PdNPs样品对革兰(氏)阳性菌具有较好的抗菌活性, 因而有望用于一些生物领域.

关键词: 钯纳米粒子, 间苯二酚杯芳烃, Suzuki-Miyuara交叉偶联反应, 纳米催化, 重复使用性能

Abstract:

Novel tetra-methoxy resorcinarene tetra-hydrazide (TMRTH) has been synthesized and used as a reducing agent and a capping agent for the synthesis of water-dispersible stable palladium nanoparticles (PdNPs). The TMRTH-PdNPs were characterized by UV-Vis spectroscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, and powder X-ray diffraction. The synthesized nanoparticles are polydispersible with a size of 5 ± 2 nm and were found to be recyclable over five cycles maintaining a catalytic activity in the Suzuki-Miyuara cross-coupling reaction. The nanocatalyst was superior in catalytic performance to conventional palladium catalysts with respect to reaction time, catalyst loading and recyclability. TMRTH-PdNPs show promise for their use in biological applications as they exhibit good antibacterial activity against gram-positive bacteria.

Key words: Palladium nanoparticle, Resorcinarene, Suzuki-Miyuara cross-coupling reaction, Nanocatalysis, Recyclability

Urvi Panchal, Krunal Modi, Manthan Panchal, Viren Mehta, Vinod K. Jain. 间苯二酚保护的抗菌Pd纳米粒子催化C-C偶联反应活性[J]. 催化学报, 2016, 37(2): 250-257.

Urvi Panchal, Krunal Modi, Manthan Panchal, Viren Mehta, Vinod K. Jain. Catalytic activity of recyclable resorcinarene-protected antibacterial Pd nanoparticles in C-C coupling reactions[J]. Chinese Journal of Catalysis, 2016, 37(2): 250-257.

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参考文献

[1] R. Tatumi, T. Akita, H. Fujihara, Chem. Commun., 2006, 3349-3351.
[2] S. Olveira, S. P. Forster, S. Seeger, J. Nanotechnol., 2014, 2014, Article ID 324089.
[3] S. Mandal, D. Roy, R. V. Chaudhari, M. Sastry, Chem. Mater., 2004, 16, 3714-3724.
[4] G. Collins, M. Schmidt, C. O'Dwyer, G. McGlacken, J. D. Holmes, ACS Catal., 2014, 4, 3105-3111.
[5] C. Petrucci, M. Cappelletti, O. Piermatti, M. Nocchetti, M. Pica, F. Pizzo, L. Vaccaro, J. Mol. Catal. A, 2015, 401, 27-34.
[6] A. Khalafi-Nezhad, F. Panahi, ACS Sustainable Chem. Eng., 2014, 2, 1177-1186.
[7] M. Nasrollahzadeh, S. M. Sajadi, E. Honarmand, M. Maham, New J. Chem., 2015, 39, 4745-4752.
[8] J. Sun, X. J. Feng, Z. R. Zhao, Y. Yamamoto, M. Bao, Tetrahedron, 2014, 70, 7166-7171.
[9] Q. M. Kainz, R. Linhardt, R. N. Grass, G. Vilé, J. Pérez-Ramírez, W. J. Stark, O. Reiser, Adv. Funct. Mater., 2014, 24, 2020-2027.
[10] R. Long, Z. L. Rao, K. K. Mao, Y. Li, C. Zhang, Q. L. Liu, C. M. Wang, Z. Y. Li, X. J. Wu, Y. J. Xiong, Angew. Chem. Int. Ed., 2015, 54, 2425-2430.
[11] S. S. Gujral, S. Khatri, P. Riyal, V. Gahlot, Indo. Global. J. Pharm. Sci., 2013, 2, 351-367.
[12] V. Polshettiwar, C. Len, A. Fihri, Coord. Chem. Rev., 2009, 253, 2599-2626.
[13] J. W. Sun, Y. S. Fu, G. Y. He, X. Q. Sun, X. Wang, Appl. Catal. B, 2015, 165, 661-667.
[14] G. D. Ding, W. T. Wang, T. Jiang, B. T. Han, Green Chem., 2013, 15, 3396-3403.
[15] T. Sun, Z. Y. Zhang, J. W. Xiao, C. Chen, F. Xiao, S. Wang, Y. Q. Liu, Sci. Rep., 2013, 3, 2527.
[16] H. Y. Shen, C. Shen, C. Chen, A. M. Wang, P. F. Zhang, Catal. Sci. Technol., 2015, 5, 2065-2071.
[17] P. D. Burton, T. J. Boyle, A. K. Datye, J. Catal., 2011, 280, 145-149.
[18] J. Cookson, Platinum Metals Rev., 2012, 56(2), 83-98.
[19] V. Huc, K. Pelzer, J. Colloid Interface Sci., 2008, 318, 1-4.
[20] H. Imahori, Y. Kashiwagi, Y. Endo, T. Hanada, Y. Nishimura, I. Yamazaki, Y. Araki, O. Ito, S. Fukuzumi, Langmuir, 2004, 20, 73-81.
[21] J. D. Senra, L. F. B. Malta, M. E. H. M. da Costa, R. C. Michel, L. C. S. Aguiar, A. B. C. Simas, O. A. C. Antunes, Adv. Synth. Catal., 2009, 351, 2411-2422.
[22] B. A. Makwana, D. J. Vyas, K. D. Bhatt, V. K. Jain, Y. K. Agrawal, Spectrochim. Acta A, 2015, 134, 73-80.
[23] V. K. Jain, P. H. Kanaiya, Russ. Chem. Rev., 2011, 80, 75-102.
[24] L. Sapozhnikova, O. Altshuler, N. Malyshenko, G. Shkurenko, E. Ostapova, B. Tryasunov, H. Altshuler, Int. J. Hydrogen Energy, 2011, 36, 1259-1263.
[25] Y. Sun, Y. Yao, C. G. Yan, Y. Han, M. Shen, ACS Nano, 2010, 4, 2129-2141.
[26] M. Luostarinen, K. Salorinne, H. Lähteenmäki, H. Mansikkamäki, C. A. Schalley, M. Nissinen, K. Rissanen, J. Inclusion Phenomena Macrocyclic. Chem., 2007, 58, 71-80.
[27] D. J. Vyas, B. A. Makwana, H. S. Gupte, K. D. Bhatt, V. K. Jain, J. Nanosci. Nanotechnol., 2012, 12, 3781-3787.
[28] D. R. Mishra, S. M. Darjee, K. D. Bhatt, K. M. Modi, V. K. Jain, J. Inclusion Phenomena Macrocyclic. Chem., 2015, 82, 425-436.
[29] J. Athilakshmi, D. K. Chand, J. Chem. Sci., 2011, 123, 875-881.
[30] T. Teranishi, M. Miyake, Chem. Mater., 1998, 10, 594-600.
[31] S. Navaladian, B. Viswanathan, T. K. Varadarajan, R. P. Viswanath, Nanoscale Res. Lett., 2009, 4, 181-186.
[32] P. Puthiaraj, W. S. Ahn, Catal. Commun., 2015, 65, 91-95.
[33] E. E. Kalu, M. Daniel, M. R. Bockstaller, Int. J. Electrochem. Sci., 2012, 7, 5297-5313.
[34] Y. L. Cui, X. N. Guo, Y. Y. Wang, X. Y. Guo, Chin. J. Catal., 2015, 36, 322-327.
[35] J. L. Zhang, L. Zhao, M. P. Song, T. C. W. Mak, Y. J. Wu, J. Organometal. Chem., 2006, 691, 1301-1306.
[36] F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron, 2008, 64, 3047-3101.
[37] A. Mousa, Synthesis and Reactivity of (PCNMe) Pincer Palladium Complexes, Lund University, Lund, 2013.
[38] B. Spellberg, J. H. Powers, E. P. Brass, L. G. Miller, J. E. Edwards Jr., Clin. Infect. Diseases, 2004, 38, 1279-1286.
[39] T. Sibanda, A. I. Okoh, Afr. J. Biotechnol., 2007, 6, 2886-2896.
[40] K. Bush, M. Macielag, Curr. Opinion Chem. Biology, 2000, 4, 433-439.
[41] A. F. Elhusseiny, H. H. A. M. Hassan, Spectrochim. Acta A, 2013, 103, 232-245.
[42] S. Y. Park, S. Y. Ryu, S. Y. Kwak, in: 2010 International Conference on Biology, Environment and Chemistry, Hong Kong, 2010.
[43] S. Kang, M. Herzberg, D. F. Rodrigues, M. Elimelech, Langmuir, 2008, 24, 6409-6413.
[44] N. C. Desai, P. N. Shihora, D. L. Moradia, Indian J. Chem. B, 2007, 46, 550-553.
[45] K. Sztanke, T. Tuzimski, J. Rzymowska, K. Pasternak, M. Kandefer-Szerszeń, Eur. J. Med. Chem., 2008, 43, 404-419.
[46] V. K. Tandon, D. B. Yadav, A. K. Chaturvedi, P. K. Shukla, Bioorg. Med. Chem. Lett., 2005, 15, 3288-3291.