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
1. [1]
  Xiaoyan Peng , Xuanhao Wu , Fan Yang , Yefei Tian , Mingming Zhang , Hongye Yuan . Gas sensors based on metal-organic frameworks: challenges and opportunities. Chinese Journal of Structural Chemistry, 2024, 43(3): 100251-100251. doi: 10.1016/j.cjsc.2024.100251
2. [2]
  Shengyong Liu , Hui Li , Wei Zhang , Yan Zhang , Yan Dong , Wei Tian . Multiple host-guest and metal coordination interactions induce supramolecular assembly and structural transition. Chinese Chemical Letters, 2025, 36(6): 110465-. doi: 10.1016/j.cclet.2024.110465
3. [3]
  Huipeng Li , Xue Yang , Minjie Sun . Self-strengthened cascade-explosive nanogel using host-guest interaction strategy for synergistic tumor treatment. Chinese Chemical Letters, 2025, 36(8): 110651-. doi: 10.1016/j.cclet.2024.110651
4. [4]
  Ran Zhu , Pan Zhang , Yitong Xu , Jiutong Ma , Qiong Jia . Design of host-guest interaction based molecularly imprinted polymers: Targeting recognition of the epitope of neuron-specific enolase via a SERS assay. Chinese Chemical Letters, 2025, 36(6): 110259-. doi: 10.1016/j.cclet.2024.110259
5. [5]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
6. [6]
  Lijun Mao , Shuo Li , Xin Zhang , Zhan-Ting Li , Da Ma . Cucurbit[n]uril-based nanostructure construction and modification. Chinese Chemical Letters, 2024, 35(8): 109363-. doi: 10.1016/j.cclet.2023.109363
7. [7]
  Saisai Yuan , Yiming Chen , Xijuan Wang , Degui Zhao , Tengyang Gao , Caiyun Wei , Chuanxiang Chen , Yang Yang , Wenjing Hong . Decouple the intermolecular interaction by encapsulating an insulating sheath. Chinese Chemical Letters, 2025, 36(6): 110816-. doi: 10.1016/j.cclet.2025.110816
8. [8]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
9. [9]
  Xiangjun Zhang , Xiaodi Yang , Yan Wang , Zhongping Xu , Sisi Yi , Tao Guo , Yue Liao , Xiyu Tang , Jianxiang Zhang , Ruibing Wang . A supramolecular nanoprodrug for prevention of gallstone formation. Chinese Chemical Letters, 2025, 36(2): 109854-. doi: 10.1016/j.cclet.2024.109854
10. [10]
  Yu-Hui Zhang , Ye Tian , Xianliang Sheng , Chen-Shuang Liu , Lu-Qiang Wei , Jie Wang , Yong Chen . Construction of a black phosphorous-based noncovalent multiple nanosupramolecular assembly for synergistic targeted photothermal and chemodynamic therapy. Chinese Chemical Letters, 2025, 36(4): 110193-. doi: 10.1016/j.cclet.2024.110193
11. [11]
  Linnan Jiang , Zhenkai Qian , Yong Chen , Xiaoyong Yu , Yugui Qiu , Wen-Wen Xu , Yonghui Sun , Xiufang Xu , Lihua Wang , Yu Liu . Double response reversible phosphorescence based on cyclodextrin supramolecular flexible elastic achieved multicolor delayed fluorescence. Chinese Chemical Letters, 2025, 36(8): 110676-. doi: 10.1016/j.cclet.2024.110676
12. [12]
  Lintao Wu , Yujia Meng , Xumei Zheng , Yiqiao Bai , Chun Han , Zhijun Wang , Jie Yang , Xiaobi Jing , Yong Yao . Pillar[5]arene based prodrug as a GSH-responsive SO₂ nanogenerator for effective gas cancer therapy. Chinese Chemical Letters, 2025, 36(9): 110808-. doi: 10.1016/j.cclet.2024.110808
13. [13]
  Xin Zhang , Zhihao Lu , Tianci Ren , Junxiang Tang , Shuo Li , Chenghao Zhu , Lijun Mao , Da Ma . Fluorescent "Texas-sized" macrocyclic receptors for the recognition and detection of nucleotides in water. Chinese Chemical Letters, 2025, 36(11): 110946-. doi: 10.1016/j.cclet.2025.110946
14. [14]
  Zhijuan Niu , Peizhe Sun , Kwangnak Koh , Changping Li . Ultrasensitive electrochemical sensor based on para-sulfonatocalix[4]arene functionalized gold nanoparticles for sulfamethazine detection. Chinese Chemical Letters, 2025, 36(11): 110844-. doi: 10.1016/j.cclet.2025.110844
15. [15]
  Yujuan Zhou , Kecheng Jie . Conformationally adaptive metal–organic cages for dynamic guest encapsulation. Chinese Chemical Letters, 2025, 36(6): 111007-. doi: 10.1016/j.cclet.2025.111007
16. [16]
  Ruolin CHENG , Yue WANG , Fei YANG , Huagen LIANG , Shijian LU . Application of metal-organic frameworks (MOFs) in photocatalytic CO₂ cycloaddition reaction: A mini review. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2429-2440. doi: 10.11862/CJIC.20250242
17. [17]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
18. [18]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
19. [19]
  Zeyuan Zhang , Zixuan Li , Chenjing Liu , Yali Hou , Ke Gao , Shijin Jian , Guoping Li , Gang He , Mingming Zhang . Porphyrin metallacage-based host-guest complexation for highly efficient photocatalytic hydrogen production. Chinese Chemical Letters, 2025, 36(12): 111322-. doi: 10.1016/j.cclet.2025.111322
20. [20]
  Ze Liu , Xiaochen Zhang , Jinlong Luo , Yingjian Yu . Application of metal-organic frameworks to the anode interface in metal batteries. Chinese Chemical Letters, 2024, 35(11): 109500-. doi: 10.1016/j.cclet.2024.109500

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1177)
HTML views(50)

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