Amphiphilic Covalent Organic Framework Nanoparticles for Pickering Emulsion Catalysis with Size Selectivity
Corresponding Author
Prof. Houbing Zou
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Shanxi Research Institute of Huairou Laboratory, Taiyuan, 030032 China
Engineering Research Center of the Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Qibiao Li
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorRongyan Zhang
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorZeshan Xiong
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorBinghua Li
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Junhao Wang
Institute of Crystalline Materials, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Runwei Wang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Qianrong Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Hengquan Yang
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Shanxi Research Institute of Huairou Laboratory, Taiyuan, 030032 China
Engineering Research Center of the Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorCorresponding Author
Prof. Houbing Zou
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Shanxi Research Institute of Huairou Laboratory, Taiyuan, 030032 China
Engineering Research Center of the Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Qibiao Li
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorRongyan Zhang
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorZeshan Xiong
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorBinghua Li
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Junhao Wang
Institute of Crystalline Materials, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorProf. Runwei Wang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Qianrong Fang
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, 130012 China
Search for more papers by this authorCorresponding Author
Prof. Hengquan Yang
Shanxi Key Laboratory of Coal-based Value-added Chemicals Green Catalysis Synthesis, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006 China
Shanxi Research Institute of Huairou Laboratory, Taiyuan, 030032 China
Engineering Research Center of the Ministry of Education for Fine Chemicals, Shanxi University, Taiyuan, 030006 China
Search for more papers by this authorGraphical Abstract
Covalent organic framework (COF) nanoparticles constructed with highly hydrophobic monomers as linkers were demonstrated to show a superior amphiphilicity for the formation of stable Pickering emulsions. Because of the high surface areas and tunable pore diameters of COFs, Pickering emulsion catalysis with both a high reaction efficiency and a remarkable size selectivity was achieved.
Abstract
Exploiting advanced amphiphilic solid catalysts is crucial to the development of Pickering emulsion catalysis. Herein, covalent organic framework (COF) nanoparticles constructed with highly hydrophobic monomers as linkers were found to show superior amphiphilicity and they were then developed as a new class of solid emulsifiers for Pickering emulsion catalysis. Employing amphiphilic COFs as solid emulsifiers, Pickering emulsions with controllable emulsion type and droplet sizes were obtained. COF materials have also been demonstrated to serve as porous surface coatings to replace traditional surface modifications for stabilizing Pickering emulsions. After implanting Pd nanoparticles into amphiphilic COFs, the obtained catalyst displayed a 3.9 times higher catalytic efficiency than traditional amphiphilic solid catalysts with surface modifications in the biphasic oxidation reaction of alcohols. Such an enhanced activity was resulted from the high surface area and regular porous structure of COFs. More importantly, because of their tunable pore diameters, Pickering emulsion catalysis with remarkable size selectivity was achieved. This work is the first example that COFs were applied in Pickering emulsion catalysis, providing a platform for exploring new frontiers of Pickering emulsion catalysis.
Conflict of interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie202314650-sup-0001-misc_information.pdf3.9 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aS. Crossley, J. Faria, M. Shen, D. E. Resasco, Science 2010, 327, 68–72;
- 1bX. Yang, X. Wang, J. Qiu, Appl. Catal. A 2010, 382, 131–137;
- 1cM. Pera-Titus, L. Leclercq, J.-M. Clacens, F. De Campo, V. Nardello-Rataj, Angew. Chem. Int. Ed. 2015, 54, 2006–2021;
- 1dZ. Wu, L. Li, T. Liao, X. Chen, W. Jiang, W. Luo, J. Yang, Z. Sun, Nano Today 2018, 22, 62–82;
- 1eD. Dedovets, Q. Li, L. Leclercq, V. Nardello-Rata, J. Leng, S. Zhao, M. Pera-Titus, Angew. Chem. Int. Ed. 2022, 61, e202107537;
- 1fL. Ni, C. Yu, Q. Wei, J. Qiu, Angew. Chem. Int. Ed. 2022, 61, e202115885.
- 2
- 2aT. Yang, L. Wei, L. Jing, J. Liang, X. Zhang, M. Tang, M. J. Monteiro, Y. Chen, Y. Wang, S. Gu, D. Zhao, H. Yang, J. Liu, G. Q. M. Lu, Angew. Chem. Int. Ed. 2017, 56, 8459–8463;
- 2bT. Zhao, X. Zhu, C. Hung, P. Wang, A. Elzatahry, A. Al-Khalaf, W. Hozzein, F. Zhang, X. Li, D. Zhao, J. Am. Chem. Soc. 2018, 140, 10009–10015;
- 2cQ. Wei, C. Yu, X. Song, Y. Zhong, L. Ni, Y. Ren, W. Guo, J. Yu, J. Qiu, J. Am. Chem. Soc. 2021, 143, 6071–6078;
- 2dY. Xi, B. Liu, S. Wang, X. Huang, H. Jiang, S. Yin, T. Ngai, X. Yang, Chem. Sci. 2021, 12, 3885–3889;
- 2eZ. Sun, R. Hübner, J. Li, C. Wu, Nat. Commun. 2022, 13, 3142;
- 2fK. Li, H. Zou, R. Ettelaie, J. Zhang, H. Yang, Angew. Chem. Int. Ed. 2023, 62, e202300794.
- 3
- 3aW. Zhou, L. Fang, Z. Fan, B. Albela, L. Bonneviot, F. De Campo, M. Pera-Titus, J. Clacens, J. Am. Chem. Soc. 2014, 136, 4869–4872;
- 3bW. Zhang, L. Fu, H. Yang, ChemSusChem 2014, 7, 391–396;
- 3cZ. Chen, L. Zhou, W. Bing, Z. Zhang, Z. Li, J. Ren, X. Qu, J. Am. Chem. Soc. 2014, 136, 7498–7504;
- 3dS. Yan, H. Zou, S. Chen, N. Xue, H. Yang, Chem. Commun. 2018, 54, 10455–10458;
- 3eZ. Sun, U. Glebe, H. Charan, A. Böker, C. Wu, Angew. Chem. Int. Ed. 2018, 57, 13810–13814.
- 4
- 4aH. Zou, H. Shi, S. Hao, Y. Hao, J. Yang, X. Tian, H. Yang, J. Am. Chem. Soc. 2023, 145, 2511–2522;
- 4bY. Zhang, R. Ettelaie, B. Binks, H. Yang, ACS Catal. 2021, 11, 1485–1494;
- 4cP. Hao, D. Schwartz, J. Medlin, ACS Catal. 2018, 8, 11165–11173.
- 5
- 5aM. Zhang, L. Wei, H. Chen, Z. Du, B. P. Binks, H. Yang, J. Am. Chem. Soc. 2016, 138, 10173–10183;
- 5bM. Zhang, R. Ettelaie, T. Yan, S. Zhang, F. Cheng, B. P. Binks, H. Yang, J. Am. Chem. Soc. 2017, 139, 17387–17396;
- 5cX. Zhang, Y. Hou, R. Ettelaie, R. Guan, M. Zhang, Y. Zhang, H. Yang, J. Am. Chem. Soc. 2019, 141, 5220–5230;
- 5dM. Zhang, R. Ettelaie, L. Dong, X. Li, T. Li, X. Zhang, B. P. Binks, H. Yang, Nat. Commun. 2022, 13, 475;
- 5eW. Wei, R. Ettelaie, X. M. Zhang, M. Fan, Y. Dong, Z. B. Li, H. Q. Yang, Angew. Chem. Int. Ed. 2022, 61, e202211912.
- 6
- 6aB. Binks, P. Fletcher, Langmuir 2001, 17, 4708–4710;
- 6bK. Du, E. Glogowski, T. Emrick, T. Russell, A. Dinsmore, Langmuir 2010, 26, 12518–12522;
- 6cS. Shi, T. Russell, Adv. Mater. 2018, 30, 1800714.
- 7
- 7aH. Yang, T. Zhou, W. Zhang, Angew. Chem. Int. Ed. 2013, 52, 7455–7459;
- 7bJ. Huang, F. Cheng, B. P. Binks, H. Yang, J. Am. Chem. Soc. 2015, 137, 15015–15025.
- 8
- 8aP. Zapata, J. Faria, M. Ruiz, R. Jentoft, D. Resasco, J. Am. Chem. Soc. 2012, 134, 8570–8578;
- 8bW. Jing, Y. Wang, Z. Shi, B. L. Peng, J. Luo, R. Wang, S. Qiu, Z. Zhang, ACS Appl. Mater. Interfaces 2020, 12, 40684–40691.
- 9
- 9aY. Zhao, X. Zhang, J. Sanjeevi, Q. Yang, J. Catal. 2016, 334, 52–59;
- 9bF. Xue, Y. Thang, F. Zhang, X. Ren, H. Yang, ACS Appl. Mater. Interfaces 2017, 9, 8403–8412;
- 9cL. Tao, M. Zhong, J. Chen, S. Jayakumar, L. Liu, H. Li, Q. Yang, Green Chem. 2018, 20, 188–196.
- 10
- 10aJ. Kim, L. J. Cote, F. Kim, W. Yuan, K. R. Shull, J. Huang, J. Am. Chem. Soc. 2010, 132, 8180–8186;
- 10bJ. Shao, W. Lv, Q. Yang, Adv. Mater. 2014, 26, 5586–5612;
- 10cF. Xi, J. Zhao, C. Shen, J. He, J. Chen, Y. Yan, K. Li, J. Liu, P. Chen, Carbon 2019, 153, 127–135.
- 11
- 11aJ. Xu, M. Antonietti, J. Am. Chem. Soc. 2017, 139, 6026–6029;
- 11bJ. Xu, C. Han, P. Meng, E. Waclawik, C. Zhang, X. Li, H. Yang, M. Antonietti, Angew. Chem. Int. Ed. 2018, 57, 14857–14861;
- 11cY. Hao, S. Hao, Q. Li, X. Liu, H. Zou, H. Yang, ACS Appl. Mater. Interfaces 2021, 13, 47236–47243.
- 12
- 12aC. S. Diercks, O. M. Yaghi, Science 2017, 355, eaal1585;
- 12bX. Y. Guan, F. Q. Chen, Q. R. Fang, S. L. Qiu, Chem. Soc. Rev. 2020, 49, 1357–1384;
- 12cK. Geng, T. He, R. Liu, S. Dalapati, K. Tan, Z. Li, S. Tao, Y. Gong, Q. Jiang, D. Jiang, Chem. Rev. 2020, 120, 8814–8933;
- 12dX. Guan, F. Chen, S. Qiu, Q. Fang, Angew. Chem. Int. Ed. 2023, 62, e202213203;
- 12eC. Wang, Z. Lv, W. Yang, X. Feng, B. Wang, Chem. Soc. Rev. 2023, 52, 1382–1427.
- 13
- 13aX. Guan, Q. Fang, Y. Yan, S. Qiu, S. Acc, Chem. Res. 2022, 55, 1912–1927;
- 13bN. Huang, R. Krishna, D. Jiang, J. Am. Chem. Soc. 2015, 137, 7079–7082;
- 13cQ. Lu, Y. Ma, H. Li, X. Guan, Y. Yusran, M. Xue, Q. Fang, Y. Yan, S. Qiu, V. Valtchev, Angew. Chem. Int. Ed. 2018, 57, 6042–6048.
- 14M. Feng, Z. Niu, C. Xing, Y. Jin, X. Feng, Y. Zhang, B. Wang, Angew. Chem. Int. Ed. 2023, 62, e202306621.
- 15
- 15aZ. Xiong, B. Sun, H. Zou, R. Wang, Q. Fang, Z. Zhang, S. Qiu, J. Am. Chem. Soc. 2022, 144, 6583–6593;
- 15bW. Ma, Q. Zheng, Y. He, G. Li, W. Guo, Z. Lin, L. Zhang, J. Am. Chem. Soc. 2019, 141, 18271–18277.
- 16
- 16aS.-Y. Ding, J. Gao, Q. Wang, Y. Zhang, W.-G. Song, C.-Y. Su, W. Wang, J. Am. Chem. Soc. 2011, 133, 19816–19822;
- 16bJ. Dong, Y. Wang, G. Liu, Y. Cheng, D. Zhao, CrystEngComm 2017, 19, 4899–4904.
- 17
- 17aH. Zou, J. Dai, J. Suo, R. Ettelaie, Y. Li, N. Xue, R. Wang, H. Yang, Nat. Commun. 2021, 12, 4968;
- 17bY. Pi, L. Cui, W. Luo, H. Li, Y. Ma, N. Ta, X. Wang, R. Gao, D. Wang, Q. Yang, J. Liu, Angew. Chem. Int. Ed. 2023, 62, e202307096.
- 18
- 18aT. Yang, L. Wei, L. Jing, J. Liang, X. Zhang, M. Tang, M. Monteiro, Y. Chen, Y. Wang, S. Gu, D. Zhao, H. Yang, J. Liu, G. Q. M. Lu, Angew. Chem. Int. Ed. 2017, 56, 8459–8463;
- 18bG. Chen, J. Han, Z. Niu, P. She, L. Li, B. Guan, J. Yu, J. Am. Chem. Soc. 2023, 145, 9021–9028.
