Citation: Jiao Cenlei, Wang Wei, Liu Jiao, Yuan Yaxian, Xu Minmin, Yao Jianlin. Surface Enhanced Raman Spectroscopy Coupled with High Performance Liquid Chromatography for Real-time Monitoring of Suzuki Coupling Reaction[J]. Acta Chimica Sinica, ;2018, 76(7): 526-530. doi: 10.6023/A18040163 shu

Surface Enhanced Raman Spectroscopy Coupled with High Performance Liquid Chromatography for Real-time Monitoring of Suzuki Coupling Reaction

College of Chemistry, Chemical Engineering and Materials Science of Soochow University, Suzhou 215123

Corresponding author: Yuan Yaxian, yuanyaxian@suda.edu.cn Yao Jianlin, jlyao@suda.edu.cn
Received Date: 20 April 2018
Available Online: 8 July 2018
Fund Project: the National Natural Science Foundation of China 21773166Project supported by the National Natural Science Foundation of China (Nos. 21673152, 21773166)the National Natural Science Foundation of China 21673152

Figures(5)

The surface enhanced Raman spectroscopy (SERS) has been employed in the structural characterization successfully due to its ultra-high sensitivity. However, it is still remained the significant difficulties in the precise interpretation of spectroscopy. Thus, it was not developed as the promising tool for monitoring the organic reaction directly. Herein, by using the two dimensional Au nanoparticles array film as substrate, the SERS was hyphenated with high performance liquid chromatography (HPLC). The individual advantages of high sensitivity of SERS and high efficiency in separation of HPLC were combined together, and it was extended successfully to real-time monitor of a Suzuki coupling reaction between 3-bromopyridine and phenylboronic acid. Firstly, the retention time and SERS spectra of standard solution of 3-bromopyridine and phenylboronic acid were performed respectively. It was beneficial for distinguishing the reactants of the current Suzuki reaction. After the reaction was proceeded for about 5 min, the mixture was sampled for the HPLC-SERS detection. It demonstrated that the chromatogram peaks located at 2.1 min and 2.8 min were contributed to phenylboronic acid and 3-bromopyridine, while 3.6 min and 15.3 min were originated from the reaction products. The solution collected at different retention times were then flowed through the catheter and dropped to the surface of Au nanoparticles arrays sequentially. The SERS spectra features were well agreement with that of 3-bromopyridine at 2.8 min, while the SERS spectra was absent for phenylboronic acid at 2.1 min due to its weak adsorption on Au surface. For the products, the typical vibrational modes of 3-phenylpyridine and diphenyl were observed in the SERS spectra, suggesting the composition of the product and byproduct. Meanwhile, the final product was confirmed by NMR spectroscopy, proving a structure of 3-phenylpyridine. Finally, the SERS results were well associated with the chromatographic peaks in a certain duration. It indicated that the HPLC-SERS technique would be a promising tool as a complementary approach to traditional techniques (such as LC-MS) for on line monitoring the organic reaction processes.
- surface enhanced Raman spectroscopy (SERS),
- high performance liquid chromatography (HPLC),
- hyphenated technique,
- Suzuki reaction,
- real-time monitor
1. [1]
  Booth, S. L.; Davidson, K. W.; Sadowski, J. A. J. Agric. Food. Chem. 1994, 42, 295. doi: 10.1021/jf00038a013
2. [2]
  Liu, X. S.; Wu, Z. Z.; Yang, K.; Ding, H. Y.; Wu, Y. J. J. Pharmaceut. Biomed. 2013, 76, 70. doi: 10.1016/j.jpba.2012.12.013
3. [3]
  Wagner, K.; Miliotis, T.; Marko-Varga, G.; Bischoff, R.; Unger, K. K. Anal. Chem. 2002, 74, 809. doi: 10.1021/ac010627f
4. [4]
  Tang, A. N.; Jiang, D. Q.; Jiang, Y.; Wang, S. W.; Yan, X. P. J. Chromatogr. A 2004, 1036, 183. doi: 10.1016/j.chroma.2004.02.065
5. [5]
  Tomas-Barberan, F. A.; Gil, M. I.; Cremin, P.; Waterhouse, A. L.; Hess-Pierce, B.; Kader, A. A. J. Agric. Food. Chem. 2001, 49, 4748. doi: 10.1021/jf0104681
6. [6]
  Cowcher, D. P.; Jarvis, R.; Goodacre, R. Anal. Chem. 2014, 86, 9977. doi: 10.1021/ac5029159
7. [7]
  Jemal, M. Biomed. Chromatogr. 2000, 14, 422. doi: 10.1002/(ISSN)1099-0801
8. [8]
  Su, D.; Chan, C. T. Y.; Gu, C.; Lim, K. S.; Chionh, Y. H.; McBee, M. E.; Russell, B. S.; Babu, I. R.; Begley, T. J.; Dedon, P. C. Nat. Protoc. 2014, 9, 828. doi: 10.1038/nprot.2014.047
9. [9]
  Ebdon, L.; Hill, S.; Ward, R. W. Analyst 1986, 111, 1113. doi: 10.1039/an9861101113
10. [10]
  Zhao, H.; Hasi, W.; Bao, L.; Han, S.; Sha, X. Y.; Sun, J.; Lou, X. T.; Lin, D. Y.; Lv, Z. W. Chin. J. Chem. 2017, 35, 1522. doi: 10.1002/cjoc.v35.10
11. [11]
  Gao, Z. G.; Zheng, T. T.; Deng, J.; Li, X. R.; Qu, Y. Y.; Lu, Y.; Liu, T. J.; Luo, Y.; Zhao, W. J.; Lin, B. C. Acta Chim. Sinica 2017, 75, 355.
12. [12]
  Su, Y.; Peng, T.; Xing, F.; Li, D.; Fan, C. Acta Chim. Sinica 2017, 75, 1036.
13. [13]
  Leng, C. B.; Wang, C.; Xiu, H. X.; Qu, X. M.; Chen, L. Z.; Tang, Q.; Li, L. Chin. J. Chem. 2016, 34, 273. doi: 10.1002/cjoc.v34.3
14. [14]
  Fan, W.; Yue-E, M.; Ling, X.; Liu, T. Chin. J. Chem. 2016, 34, 73. doi: 10.1002/cjoc.201500585
15. [15]
  Cabalin, L. M.; Ruperez, A.; Laserna, J. J. Talanta 1993, 40, 1741. doi: 10.1016/0039-9140(93)80092-6
16. [16]
  Sagmuller, B.; Schwarze, B.; Brehm, G.; Trachta, G.; Schneider, S. J. Mol. Struct. 2003, 661, 279.
17. [17]
  Sheng, R.; Ni, F.; Cotton, T. M. Anal. Chem. 1991, 63, 437. doi: 10.1021/ac00005a010
18. [18]
  Carrillo-Carrion, C.; Simonet, B. M.; Valcarcel, M.; Lendl, B. J. Chromatogr. A 2012, 1225, 55. doi: 10.1016/j.chroma.2011.12.002
19. [19]
  Zhang, Z. M.; Liu, J. F.; Liu, R.; Sun, J. F.; Wei, G. H. Anal. Chem. 2014, 86, 7286. doi: 10.1021/ac5017387
20. [20]
  Wang, W.; Xu, M. M.; Guo, Q. H.; Yuan, Y. X.; Gu, R. A.; Yao, J. L. RSC Adv. 2015, 5, 47640. doi: 10.1039/C5RA05562H
21. [21]
  Zhang, C. J.; Zhang, J.; Lin, J. R.; Jin, Q.; Xu, M. M.; Yao, J. L. Acta Chim. Sinica 2017, 75, 860.
22. [22]
  Miyaura, N.; Suzuki, A. J. Chem. Soc. Chem. Commun. 1979, 866.
23. [23]
  Miyaura, N.; Kinji, Y.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437. doi: 10.1016/S0040-4039(01)95429-2
24. [24]
  Zhang, E.; Tang, J.; Li, S.; Wu, P.; Moses, J. E.; Sharpless, K. B. Chem. Eur. J. 2016, 22, 1. doi: 10.1002/chem.201504553
25. [25]
  Jacquemin, M.; Hauwaert, D.; Debecker, D. P.; Gaigneaux, E. M. J. Mol. Catal. 2016, 416, 47. doi: 10.1016/j.molcata.2016.02.022
26. [26]
  Pahlevanneshan, Z.; Moghadam, M.; Mirkhani, V.; Tangestaninejad, S.; Mohammadpoore-Baltork, I.; Loghmani-Khouzani, H. J. Organomet. Chem. 2016, 809, 31. doi: 10.1016/j.jorganchem.2016.02.019
27. [27]
  Guo, Q. H.; Xu, M. M.; Yuan, Y. X.; Gu, R. A.; Yao, J. L. Langmuir 2016, 32, 4530. doi: 10.1021/acs.langmuir.5b04393
28. [28]
  Liu, C.; Han, N.; Song, X. X.; Qiu, J. S. Eur. J. Org. Chem. 2010, 5548.
29. [29]
  Wei, J. F.; Jiao, J.; Feng, J. J.; Lv, J.; Zhang, X. R.; Shi, X. Y.; Chen, Z. G. J. Org. Chem. 2009, 74, 6283. doi: 10.1021/jo900481y
30. [30]
  Frens, G. Nat. Phys. Sci. 1973, 241, 20. doi: 10.1038/physci241020a0
31. [31]
  Fang, P. P.; Li, J. F.; Yang, Z. L.; Li, L. M.; Ren, B.; Tian, Z. Q. J. Raman Spectrosc. 2008, 39, 1679. doi: 10.1002/jrs.v39:11
32. [32]
  Zhang, E.; Tang, J.; Li, S.; Wu, P.; Moses, J. E.; Sharpless, K. B. Chem. Eur. J. 2016, 22, 5692. doi: 10.1002/chem.201600167
1. [1]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
2. [2]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
3. [3]
  Siyu Zhang , Kunhong Gu , Bing'an Lu , Junwei Han , Jiang Zhou . Hydrometallurgical Processes on Recycling of Spent Lithium-lon Battery Cathode: Advances and Applications in Sustainable Technologies. Acta Physico-Chimica Sinica, 2024, 40(10): 2309028-. doi: 10.3866/PKU.WHXB202309028
4. [4]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
5. [5]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
6. [6]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
7. [7]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
8. [8]
  Jiao CHEN , Yi LI , Yi XIE , Dandan DIAO , Qiang XIAO . Vapor-phase transport of MFI nanosheets for the fabrication of ultrathin b-axis oriented zeolite membranes. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 507-514. doi: 10.11862/CJIC.20230403
9. [9]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
10. [10]
  Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
11. [11]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
12. [12]
  Zizheng LU , Wanyi SU , Qin SHI , Honghui PAN , Chuanqi ZHAO , Chengfeng HUANG , Jinguo PENG . Surface state behavior of W doped BiVO₄ photoanode for ciprofloxacin degradation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 591-600. doi: 10.11862/CJIC.20230225
13. [13]
  Xinlong WANG , Zhenguo CHENG , Guo WANG , Xiaokuen ZHANG , Yong XIANG , Xinquan WANG . Enhancement of the fragile interface of high voltage LiCoO₂ by surface gradient permeation of trace amounts of Mg/F. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 571-580. doi: 10.11862/CJIC.20230259
14. [14]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
15. [15]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
16. [16]
  Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
17. [17]
  Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
18. [18]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
19. [19]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
20. [20]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1291)
HTML views(344)

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