Research Progress in Metal-Porous Organic Cage Nanocomposites

doi:10.6023/cjoc202207020

Abstract

Porous organic molecular cage (POC) is a kind of discrete molecule with specific sized cavities. Due to stable pore structure, high specific surface area, and good solubility, POC is emerging as a promising multi-functional material by accepting specific-sized molecules or ions within the cavity. In addition, derived from the stable and open pores, POCs can be utilized to a variety of applications, such as gas separation and storage, sensors, drug delivery, and so on, which is becoming a research hotspot at home and abroad. At present, given to the strong binding sites with metal nanoparticles (MNPs) and spatial confinement effect within the cage, POCs provide a new and stable way to protect metal nanoparticles from aggregation. Therefore, POCs are often used to prepare the metal nanoparticles of specific size, forming the metal-porous organic cage nanocomposites. The advantage of POCs in the metal-POCs nanocomposite is not only to regulate the size of metal nanoparticles but also to stabilize the micro/nanostructures without affecting the surface accessibility of active atoms within cages. Compared with traditional method to stabilize catalytic nanoparticles, MNPs-POCs composite has better stability and more active catalytic centers. The recent research achievements in MNPs-POCs nanocomposites and their important applications are summarized in this review, which is expected to inspire the further application in catalysis, sensors, medicine, etc.

Key words: porous organic cage, metal nanoparticles, nanocomposites, surface atom accessibility

Cite this article

Jialin Chen, Zhiheng Ma, Yufeng Li, Siwei Cao, Qiang Zhuang. Research Progress in Metal-Porous Organic Cage Nanocomposites[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 120-129.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

Figure 1. (a) Molecular structures of Cage 1, Cage 2 and Cage 3,[16] (b) synthesis of Cage 3a,[17] and (c) cationic cage synthesized by Lei[18]

Figure 2. (a) Dynamic self-assembly synthesis method based on boron ester generation proposed by Iwasawa[20], (b) large porous organic molecules constructed by Zhang[21], and (c) cages 1, 2 constructed by Ivanova[22]

Figure 3. (a) Alkyne redecomposition route of COP-5[23], (b) one-step alkyne redecomposition reaction of 4D2h[24], and (c) the outer cavity structure of [8???+12] borate cage formed by olefin redecomposition reaction[25]

Figure 4. (a) cage-1 and cage-2 constructed by DABCO[29], and (b) cage-3 and cage-4[30]

Figure 5. (a) Au NPs synthesized by Zhang[32], and (b) Fh@- MOC synthesized by Masayuki[35]

Figure 6. (a) Au-NPs self-assemble on octahedral crystal plane to form monolayer film[37], and (b) Fe3O4-NPs formation of dense monolayer ferrite nanosuperlattice[38]

Figure 7. Semi-heterogeneous palladium-enzyme integration catalyst prepared by Gao[43]

References 48

[1]	Moran, J. R.; Karbach, S.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 5826. doi: 10.1021/ja00385a064
[2]	(a) Anderson, S.; Anderson, H. L.; Sanders, J. K. Acc. Chem. Res. 1993, 26, 469. doi: 10.1021/ar00033a003 pmid: 18213980
	(b) Diederich, F.; Stang, P. J. Templated Organic Synthesis, John Wiley & Sons, New Jersey, 2008, pp. 100-120. pmid: 18213980
	(c) Meyer, C. D.; Joiner, C. S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 1705. pmid: 18213980
[3]	(a) Hasell, T.; Miklitz, M.; Stephenson, A.; Little, M. A.; Chong, S. Y.; Clowes, R.; Chen, L.; Holden, D.; Tribello, G. A.; Jelfs, K. E. J. Am. Chem. Soc. 2016, 138, 1653. doi: 10.1021/jacs.5b11797 pmid: 26757885
	(b) Wang, Z.; Sikdar, N.; Wang, S.Q.; Li, X.; Yu, M.; Bu, X. H.; Chang, Z.; Zou, X.; Chen, Y.; Cheng, P. J. Am. Chem. Soc. 2019, 141, 9408. doi: 10.1021/jacs.9b04319 pmid: 26757885
	(c) Chen, L.; Reiss, P. S.; Chong, S. Y.; Holden, D.; Jelfs, K. E.; Hasell, T.; Little, M. A.; Kewley, A.; Briggs, M. E.; Stephenson, A. Nat. Mater. 2014, 13, 954. doi: 10.1038/nmat4035 pmid: 26757885
[4]	(a) Leonhardt, V.; Fimmel, S.; Krause, A. M.; Beuerle, F. Chem. Sci. 2020, 11, 8409. doi: 10.1039/d0sc03131c pmid: 34123100
	(b) Duan, H.; Li, Y.; Li, Q.; Wang, P.; Liu, X.; Cheng, L.; Yu, Y.; Cao, L. Angew. Chem. 2020, 132, 10187. doi: 10.1002/ange.201912730 pmid: 34123100
	(c) Tamura, Y.; Takezawa, H.; Fujita, M. J. Am. Chem. Soc. 2020, 142, 5504. doi: 10.1021/jacs.0c00459 pmid: 34123100
[5]	Wang, Y.; Yang, Y.; Zha, Z.; Wang, J.; Wang, Z.; Zhao, S. J. Membr. Sci. 2022, 120782.
[6]	(a) Brammer, L. Chem. Soc. Rev. 2004, 33, 476. pmid: 15480472
	(b) Jones, N. Nature 2014, 505, 602. doi: 10.1038/505602a pmid: 15480472
[7]	(a) Song, L. N.; Zou, L. C.; Wang, X. X.; Luo, N.; Xu, J. J.; Yu, J. H. iScience 2019, 14, 36. doi: 10.1016/j.isci.2019.03.013
	(b) Kim, B. H.; Hackett, M. J.; Park, J.; Hyeon, T. Chem. Mater. 2014, 26, 59. doi: 10.1021/cm402225z
	(c) Dong, C.; Li, Y.; Cheng, D.; Zhang, M.; Liu, J.; Wang, Y. G.; Xiao, D.; Ma, D. ACS Catal. 2020, 10, 11011. doi: 10.1021/acscatal.0c02818
[8]	(a) Pattadar, D. K.; Zamborini, F. P. Langmuir 2019, 35, 16416. doi: 10.1021/acs.langmuir.9b02421 pmid: 31647240
	(b) Jamkhande, P. G.; Ghule, N. W.; Bamer, A. H.; Kalaskar, M. G. J. Drug Delivery Sci. Technol. 2019, 53, 101174. doi: 10.1016/j.jddst.2019.101174 pmid: 31647240
[9]	Kang, H.; Joseph, T.B.; Rebeca, S. Chem. Rev. 2018, 119, 664,699. doi: 10.1021/acs.chemrev.8b00341
[10]	Wang, S.; Zhang, W.; Yang, Z.; Wei, H.; Yang, Y.; Wei, J. Catal. Lett. 2019, 149, 2492. doi: 10.1007/s10562-019-02858-9
[11]	Ashton, P. R.; Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Raymo, F. M.; Slawin, A. M.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1993, 115, 5422. doi: 10.1021/ja00066a010
[12]	(a) Jin, Y.; Yu, C.; Denman, R. J.; Zhang, W. Chem. Soc. Rev. 2013, 42, 6634. doi: 10.1039/c3cs60044k
	(b) Jin, Y.; Wang, Q.; Taynton, P.; Zhang, W. Acc. Chem. Res. 2014, 47, 1575. doi: 10.1021/ar500037v
[13]	Hasell, T.; Cooper, A. I. Nat. Rev. Mater. 2016, 1, 1.
[14]	Quan, M. L.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2754. doi: 10.1021/ja00007a060
[15]	Ro, S.; Rowan, S. J.; Pease, A. R.; Cram, D. J.; Stoddart, J. F. Org. Lett. 2000, 2, 2411. pmid: 10956509
[16]	Tozawa, T.; Jones, J. T.; Swamy, S. I.; Jiang, S.; Adams, D. J.; Shakespeare, S.; Clowes, R.; Bradshaw, D.; Hasell, T.; Chong, S. Y. Nat. Mater. 2009, 8, 973. doi: 10.1038/nmat2545
[17]	Qiu, L.; McCaffrey, R.; Jin, Y.; Gong, Y.; Hu, Y.; Sun, H.; Park, W.; Zhang, W. Chem. Sci. 2018, 9, 676. doi: 10.1039/c7sc03148c pmid: 29629135
[18]	Lei, Y.; Chen, Q.; Liu, P.; Wang, L.; Wang, H.; Li, B.; Lu, X.; Chen, Z.; Pan, Y.; Huang, F. Angew. Chem. 2021, 133, 4755. doi: 10.1002/ange.202013045
[19]	Liu, Q. Y.; Zhang, L.; Mo, F. Y. Acta Chim. Sin. 2020, 78, 1297. (in Chinese)
	(刘谦益, 张雷, 莫凡洋, 化学学报, 2020, 78, 1297.) doi: 10.6023/A20070294
[20]	Iwasawa, N.; Takahagi, H. J. Am. Chem. Soc. 2007, 129, 7754. doi: 10.1021/ja072319q
[21]	Zhang, G.; Presly, O.; White, F.; Oppel, I. M.; Mastalerz, M. Angew. Chem. Int. Ed. 2014, 53, 1516. doi: 10.1002/anie.201308924 pmid: 24403008
[22]	Ivanova, S.; Köster, E.; Holstein, J. J.; Keller, N.; Clever, G. H.; Bein, T.; Beuerle, F. Angew. Chem. Int. Ed. 2021, 60, 17455. doi: 10.1002/anie.202102982
[23]	Zhang, C.; Wang, Q.; Long, H.; Zhang, W. J. Am. Chem. Soc. 2011, 133, 20995. doi: 10.1021/ja210418t
[24]	Wang, Q.; Zhang, C.; Noll, B. C.; Long, H.; Jin, Y.; Zhang, W. Angew. Chem. Int. Ed. 2014, 53, 10663. doi: 10.1002/anie.201404880 pmid: 25146457
[25]	Hähsler, M.; Mastalerz, M. Chem.-Eur. J. 2021, 27, 233. doi: 10.1002/chem.202003675
[26]	(a) Stefankiewicz, A. R.; Sambrook, M. R.; Sanders, J. K. Chem. Sci. 2012, 3, 2326. doi: 10.1039/c2sc20347b
	(b) Sun, W. D.; Ye, L.; Liu, J.; Zheng, L.; Guo, W. C.; Han, S. K.; Shao, C. K.; Jiang, H. Chin. J. Org. Chem. 2019, 39, 2867. (in Chinese) doi: 10.6023/cjoc201904042
	(孙卫东, 叶琳, 刘佳, 郑璐, 郭文彩, 韩森凯, 邵成园, 江华, 有机化学, 2019, 39, 2867.) doi: 10.6023/cjoc201904042
[27]	Schäfer, N.; Bühler, M.; Heyer, L.; Röhr, M. I.; Beuerle, F. Chem.-Eur. J. 2021, 27, 6077. doi: 10.1002/chem.202005276
[28]	Zhang, J.; Li, Y.; Yang, W.; Lai, S. W.; Zhou, C.; Liu, H.; Che, C. M.; Li, Y. Chem. Commun. 2012, 48, 3602. doi: 10.1039/c2cc17270d
[29]	Ding, H.; Meng, X.; Cui, X.; Yang, Y.; Zhou, T.; Wang, C.; Zeller, M.; Wang, C. Chem. Commun. 2014, 50, 11162. doi: 10.1039/C4CC05449K
[30]	Ding, H.; Wu, X.; Zeller, M.; Xie, Y.; Wang, C. J. Org. Chem. 2015, 80, 9360. doi: 10.1021/acs.joc.5b01781
[31]	Chen, M.; Feng, Y.; Wang, X.; Chen, T.; Zhang, J..; Qian, D. Langmuir 2007, 23,5296-5304. doi: 10.1021/la700553d
[32]	McCaffrey, R.; Long, H.; Jin, Y.; Sanders, A.; Park, W.; Zhang, W. J. Am. Chem. Soc. 2014, 136, 1782. doi: 10.1021/ja412606t pmid: 24432779
[33]	Nihei, M.; Ida, H.; Nibe, T.; Moeljadi, A. M. P.; Trinh, Q. T.; Hirao, H.; Ishizaki, M.; Kurihara, M.; Shiga, T.; Oshio, H. J. Am. Chem. Soc. 2018, 140, 17753. doi: 10.1021/jacs.8b10957
[34]	Gálvez, N.; Fernández, B.; Sánchez, P.; Cuesta, R.; Ceolín, M.; Clemente León, M.; Trasobares, S.; López Haro, M.; Calvino, J. J.; Stéphan, O. J. Am. Chem. Soc. 2008, 130, 8062. doi: 10.1021/ja800492z
[35]	Skowronek, P.; Warżajtis, B.; Rychlewska, U.; Gawroński, J. Chem. Commun. 2013, 49, 2524. doi: 10.1039/c3cc39098e
[36]	Hua, M.; Wang, S.; Gong, Y.; Wei, J.; Yang, Z.; Sun, J. K. Angew. Chem. Int. Ed. 2021, 60, 12490. doi: 10.1002/anie.202100849
[37]	Hua, M.; Hao, J.; Gong, Y.; Zhang, F.; Wei, J.; Yang, Z.; Pileni, M. P. ACS Nano 2020, 14, 5517. doi: 10.1021/acsnano.9b09686
[38]	Ren, F.; Hua, M.; Yang, Z.; Wei, J. J. Colloid Interface Sci. 2022, 621, 331. doi: 10.1016/j.jcis.2022.04.027
[39]	Bai, S.; Wang, Y. Y.; Han, Y. F. Chin. J. Chem. 2019, 37, 1289. doi: 10.1002/cjoc.201900366
[40]	(a) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461. doi: 10.1021/ar800036s
	(b) Fu, Y. F.; Zou, Z. J.; Tang, C.; Song, K. P. Chin. J. Org. Chem. 2018, 38, 3106. (in Chinese) doi: 10.6023/cjoc201803027
	(付玉芳, 邹志娟, 唐成, 宋昆鹏, 有机化学, 2018, 38, 3106.) doi: 10.6023/cjoc201803027
[41]	Zhou, Y.; Xiang, Z.; Cao, D.; Liu, C. J. Chem. Commun. 2013, 49, 5633. doi: 10.1039/c3cc00287j
[42]	Jiang, S.; Cox, H. J.; Papaioannou, E. I.; Tang, C.; Liu, H.; Murdoch, B. J.; Gibson, E. K.; Metcalfe, I. S.; Evans, J. S.; Beaumont, S. K. Nanoscale 2019, 11, 14929. doi: 10.1039/c9nr04553h pmid: 31361283
[43]	Gao, S.; Liu, Y.; Wang, L.; Wang, Z.; Liu, P.; Gao, J.; Jiang, Y. ACS Catal. 2021, 11, 5544. doi: 10.1021/acscatal.1c00587
[44]	(a) Acharyya, K.; Mukherjee, P. S. Chem.-Eur. J. 2015, 21, 6823. doi: 10.1002/chem.201406581 pmid: 25786976
	(b) Brzechwa Chodzyńska, A.; Drożdż, W.; Harrowfield, J.; Stefankiewicz, A. R. Coord. Chem. Rev. 2021, 434, 213820. doi: 10.1016/j.ccr.2021.213820 pmid: 25786976
[45]	Ren, H.; Liu, C.; Ding, X.; Fu, X.; Wang, H.; Jiang, J. Chin. J. Chem. 2022, 40, 385. doi: 10.1002/cjoc.202100612
[46]	Guo, Z. B.; Zheng, X. Y.; Li, X. Y.; Jia, Q. F.; Zhang, P. Z.; Wei, C.; Li, X. L. Chin. J. Org. Chem. 2020, 40, 1239. (in Chinese) doi: 10.6023/cjoc201911015
	(郭振波, 郑雪阳, 李雪艳, 贾清菲, 张平竹, 魏超, 李小六, 有机化学, 2020, 40, 1239.) doi: 10.6023/cjoc201911015
[47]	(a) Zhang, X. D.; Wu, D.; Shen, X.; Chen, J.; Sun, Y. M.; Liu, P. X.; Liang, X. J. Biomaterials 2012, 33, 6408. doi: 10.1016/j.biomaterials.2012.05.047 pmid: 20101074
	(b) Rezaee, M.; Hunting, D. J.; Sanche, L. Int. J. Radiat. Oncol. Biol. Phys. 2013, 87, 847. doi: 10.1016/j.ijrobp.2013.06.2037 pmid: 20101074
	(c) Porcel, E.; Liehn, S.; Remita, H.; Usami, N.; Kobayashi, K.; Furusawa, Y.; Le Sech, C.; Lacombe, S. Nanotechnology 2010, 21, 85103. doi: 10.1088/0957-4484/21/8/085103 pmid: 20101074
[48]	Liu, H.; Duan, X.; Lv, Y. K.; Zhu, L.; Zhang, Z.; Yu, B.; Jin, Y.; Si, Y.; Wang, Z.; Li, B. Chem. Eng. J. 2021, 426, 130872. doi: 10.1016/j.cej.2021.130872

金属-多孔有机分子笼纳米复合物的研究进展