Citation: Hongwen Chen, Huaqiang Chen, Bo Zhang, Liming Jiang, Youqing Shen, Engang Fu, Dan Zhao, Zhuxian Zhou. Tuning the release rate of volatile molecules by pore surface engineering in metal-organic frameworks[J]. Chinese Chemical Letters, ;2021, 32(6): 1988-1992. doi: 10.1016/j.cclet.2020.10.035 shu

Tuning the release rate of volatile molecules by pore surface engineering in metal-organic frameworks

Hongwen Chen ^a ,
Huaqiang Chen ^c ,
Bo Zhang ^a ,
Liming Jiang ^b ,
Youqing Shen ^a ,
Engang Fu ^c ,
Dan Zhao ^d ,
Zhuxian Zhou ^{a, *,}

a.
Key Laboratory of Biomass Chemical Engineering of Ministry of Education and Center for Bionanoengineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
b.
Key Laboratory of Macromolecular Synthesis and Functionalization of Ministry of Education, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
c.
State Key Laboratory of Nuclear Physics and Technology, School of Physics, Peking University, Beijing 100871, China
d.
Department of Chemical & Biomolecular Engineering, National University of Singapore, Singapore 117585, Singapore

zhouzx@zju.edu.cn

Received Date: 21 September 2020
Revised Date: 16 October 2020
Accepted Date: 22 October 2020
Available Online: 23 October 2020

Figures(5)

Encapsulation and controlled release of volatile molecules such as fragrances in a designed manner is important but challenging for the flavor and fragrance industry. Here, we report the tuning release of volatile molecules by postsynthetic modification of an amine-terminated metal-organic framework (MOF) MIL-101-NH₂. By amidation, we obtained three MIL-101 MOFs, the trimethylacetamide-terminated TC-MIL-101, the benzamide-terminated BC-MIL-101, and the oxalic acid monoamide-terminated OC-MIL-101. All the MOFs can efficiently encapsulate volatile molecules. Moreover, we demonstrate that the release profile of volatiles can be widely tuned to sustain the release in several days to months and even over a year using different modified MIL-101 MOFs. We show that the release profiles are correlated with the binding energies between the guest volatiles and pores in MOFs. The pore diffusion and the synergistic transport are the rate-limiting step of the guest molecules from the modified MOFs.
- Metal-organic frameworks (MOFs),
- Postsynthetic modification,
- Encapsulation and sustained-release,
- Fragrances,
- Host-guest interaction
1. [1]
  B. Adorjan, G. Buchbauer, Flavour Frag. J. 25 (2010) 407-426. doi: 10.1002/ffj.2024
2. [2]
  A. Haehner, H. Maass, I. Croy, T. Hummel, Flavour Frag. J. 32 (2017) 24-28. doi: 10.1002/ffj.3339
3. [3]
  C. Chrea, D. Grandjean, S. Delplanque, et al., Chem. Senses 34 (2009) 49-62.
4. [4]
  A. Herrmann, Angew. Chem. Int. Ed. 46 (2007) 5836-5863. doi: 10.1002/anie.200700264
5. [5]
  B. Pena, C. Panisello, G. Areste, R. Garcia-Valls, T. Gumi, Chem. Eng. J. 179 (2012) 394-403. doi: 10.1016/j.cej.2011.10.090
6. [6]
  Y. Liu, K. Liu, M. Zhao, et al., React. Funct. Polym. 132 (2018) 138-144. doi: 10.1016/j.reactfunctpolym.2018.09.021
7. [7]
  R. Tekin, N. Bac, J. Warzywoda, A. Sacco, Microporous Mesoporous Mater. 215 (2015) 51-57. doi: 10.1016/j.micromeso.2015.05.020
8. [8]
  B. Strzemiecka, M. Kasperkowiak, M. Lozynski, D. Paukszta, A. Voelkel, Microporous Mesoporous Mater. 161 (2012) 106-114. doi: 10.1016/j.micromeso.2012.05.024
9. [9]
  Y. Liu, Y. Wang, J. Huang, et al., AlChE J. 65 (2019) 491-499. doi: 10.1002/aic.16461
10. [10]
  B. Zhang, J. Huang, K. Liu, et al., Ind. Eng. Chem. Res. 58 (2019) 19767-19777. doi: 10.1021/acs.iecr.9b04214
11. [11]
  A.M. Shultz, O.K. Farha, J.T. Hupp, S.T. Nguyen, J. Am. Chem. Soc. 131 (2009) 4204-4205. doi: 10.1021/ja900203f
12. [12]
  A. Schneemann, V. Bon, I. Schwedler, et al., Chem. Soc. Rev. 43 (2014) 6062-6096. doi: 10.1039/C4CS00101J
13. [13]
  Z. Han, W. Shi, P. Cheng, Chin. Chem. Lett. 29 (2018) 819-822. doi: 10.1016/j.cclet.2017.09.050
14. [14]
  X. Wang, W. Chen, H. Qi, et al., Chem. Eur. J. 23 (2017) 7990-7996. doi: 10.1002/chem.201700474
15. [15]
  Z. Hu, B.J. Deibert, J. Li, Chem. Soc. Rev. 43 (2014) 5815-5840. doi: 10.1039/C4CS00010B
16. [16]
  K. Sheng, H. Lu, A. Sun, et al., Chin. Chem. Lett. 30 (2019) 895-898. doi: 10.1016/j.cclet.2019.01.027
17. [17]
  D. Zhao, S. Tan, D. Yuan, et al., Adv. Mater. 23 (2011) 90-93. doi: 10.1002/adma.201003012
18. [18]
  Z. Dong, Y. Sun, J. Chu, X. Zhang, H. Deng, J. Am. Chem. Soc. 139 (2017) 14209-14216. doi: 10.1021/jacs.7b07392
19. [19]
  J. Della Rocca, D. Liu, W. Lin, Acc. Chem. Res. 44 (2011) 957-968. doi: 10.1021/ar200028a
20. [20]
  X. Cui, K. Chen, H. Xing, et al., Science 353 (2016) 141-144. doi: 10.1126/science.aaf2458
21. [21]
  X. Kong, H. Deng, F. Yan, et al., Science 341 (2013) 882-885. doi: 10.1126/science.1238339
22. [22]
  M. Ding, X. Cai, H.L. Jiang, Chem. Sci. 10 (2019) 10209-10230. doi: 10.1039/C9SC03916C
23. [23]
  S. Yang, L. Peng, D. Sun, et al., Chem. Sci. 10 (2019) 4542-4549. doi: 10.1039/C9SC00135B
24. [24]
  H. Jiang, D. Feng, T. Liu, J. Li, H. Zhou, J. Am. Chem. Soc. 134 (2012) 14690-14693. doi: 10.1021/ja3063919
25. [25]
  N.C. Burtch, H. Jasuja, K.S. Walton, Chem. Rev. 114 (2014) 10575-10612. doi: 10.1021/cr5002589
26. [26]
  M. Kim, J.F. Cahill, H. Fei, K.A. Prather, S.M. Cohen, J. Am. Chem. Soc. 134 (2012) 18082-18088. doi: 10.1021/ja3079219
27. [27]
  K.K. Tanabe, S.M. Cohen, Chem. Soc. Rev. 40 (2011) 498-519. doi: 10.1039/C0CS00031K
28. [28]
  F. Zhou, J. Zhou, X. Gao, C. Kong, L. Chen, RSC Adv. 7 (2017) 3713-3719. doi: 10.1039/C6RA25396B
29. [29]
  Z. Wang, K.K. Tanabe, S.M. Cohen, Chem. Eur. J. 16 (2010) 212-217. doi: 10.1002/chem.200902158
30. [30]
  J. Wang, X. Huang, H. Gao, A. Li, C. Wang, Chem. Eng. J. 350 (2018) 164-172. doi: 10.1016/j.cej.2018.05.190
31. [31]
  Y. Lin, C. Kong, L. Chen, RSC Adv. 2 (2012) 6417-6419. doi: 10.1039/c2ra20641b
32. [32]
  H. Liu, D. Ramella, P. Yu, Y. Luan, RSC Adv. 7 (2017) 22353-22359. doi: 10.1039/C7RA00296C
33. [33]
  H. Hintz, S. Wuttke, Chem. Mater. 26 (2014) 6722-6728. doi: 10.1021/cm502920f
34. [34]
  Q. Xie, Y. Li, Z. Lv, et al., Sci. Rep. 7 (2017) 3316. doi: 10.1038/s41598-017-03526-x
35. [35]
  P. Karthik, R. Vinoth, P. Zhang, et al., ACS Appl. Energy Mater. 1 (2018) 1913-1923. doi: 10.1021/acsaem.7b00245
36. [36]
  S. Plimpton, J. Comput. Phys. 117 (1995) 1-19. doi: 10.1006/jcph.1995.1039
37. [37]
  J. Huang, B. Wu, Z. Zhou, et al., Nanomedicine 21 (2019) 102058. doi: 10.1016/j.nano.2019.102058
38. [38]
  R.W. Korsmeyer, R. Gurny, E. Doelker, P. Buri, N.A. Peppas, Int. J. Pharm. 15 (1983) 25-35. doi: 10.1016/0378-5173(83)90064-9
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