Citation: Can HE, Tian-Pu SHENG, Feng-Rong DAI, Zhong-Ning CHEN. Sulfonylcalix[4]arene-based Coordination Supercontainers[J]. Chinese Journal of Structural Chemistry, ;2020, 39(12): 2077-2084. doi: 10.14102/j.cnki.0254–5861.2011–3029 shu

Sulfonylcalix[4]arene-based Coordination Supercontainers

a.
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: Feng-Rong DAI, dfr@fjirsm.ac.cn
Received Date: 3 November 2020
Accepted Date: 16 November 2020

Fund Project: the National Natural Science Foundation of China 21673239the National Natural Science Foundation of China 21501179

Figures(8)

Sulfonylcalix[4]arenes-based coordination containers, namely metal-organic supercontainers (MOSCs), are a new class of coordination containers constructed from the self-assembly of divalent metal ions, suitable carboxylate linkers, and sulfonylcalix[4]arenes container precursor. MOSCs feature both endo cavity surrounded by carboxylate linkers and exo cavities originated from the upper rim of sulfonylcalix[4]arenes. The molecular topologies and endo cavity of MOSCs are tuneable via judicious design of carboxylate linkers, while the modulation of endo cavity are accessible by chemical modification on the para substituent group of the sulfonylcalix[4]arenes. In this paper, recent advances and typical examples of design and functionalization of MOSCs are presented.
- coordination container,
- sulfonylcalix[4]arene,
- metal-organic supercontainer,
- self-assembly
1. [1]
  Leininger, S.; Olenyuk, B.; Stang, P. J. Self-assembly of discrete cyclic nanostructures mediated by transition metals. Chem. Rev. 2000, 100, 853–907. doi: 10.1021/cr9601324
2. [2]
  Chakrabarty, R.; Mukherjee, P. S.; Stang, P. J. Supramolecular coordination: self-assembly of finite two- and three-dimensional ensembles. Chem. Rev. 2011, 111, 6810–6918. doi: 10.1021/cr200077m
3. [3]
  Cook, T. R.; Zheng, Y. R.; Stang, P. J. Metal-organic frameworks and self-assembled supramolecular coordination complexes: comparing and contrasting the design, synthesis, and functionality of metal-organic materials. Chem. Rev. 2013, 113, 734–777. doi: 10.1021/cr3002824
4. [4]
  Bi, Y.; Du, S.; Liao, W. Thiacalixarene-based nanoscale polyhedral coordination cages. Coord. Chem. Rev. 2014, 276, 61–72. doi: 10.1016/j.ccr.2014.06.011
5. [5]
  Cook, T. R.; Stang, P. J. Recent developments in the preparation and chemistry of metallacycles and metallacages via coordination. Chem. Rev. 2015, 115, 7001–7045. doi: 10.1021/cr5005666
6. [6]
  Zhang, Y. Y.; Gao, W. X.; Lin, L.; Jin, G. X. Recent advances in the construction and applications of heterometallic macrocycles and cages. Coord. Chem. Rev. 2017, 344, 323–344. doi: 10.1016/j.ccr.2016.09.010
7. [7]
  Li, X. X.; Zhao, D.; Zheng, S. T. Recent advances in POM-organic frameworks and POM-organic polyhedra. Coord. Chem. Rev. 2019, 397, 220–240. doi: 10.1016/j.ccr.2019.07.005
8. [8]
  Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base. Tetrahedron Lett. 1997, 38, 3971–3972. doi: 10.1016/S0040-4039(97)00792-2
9. [9]
  Kajiwara, T.; Katagiri, K.; Hasegawa, M.; Ishii, A.; Ferbinteanu, M.; Takaishi, S.; Ito, T.; Yamashita, M.; Iki, N. Conformation-controlled luminescent properties of lanthanide clusters containing p-tert-butylsulfonylcalix[4]arene. Inorg. Chem. 2006, 45, 4880–4882. doi: 10.1021/ic060397t
10. [10]
  Karashimada, R.; Iki, N. Thiacalixarene assembled heterotrinuclear lanthanide clusters comprising Tb(Ⅲ) and Yb(Ⅲ) enable f-f communication to enhance Yb(Ⅲ)-centred luminescence. Chem. Commun. 2016, 52, 3139–3142. doi: 10.1039/C5CC09612J
11. [11]
  Bi, Y.; Wang, X. T.; Liao, W.; Wang, X.; Deng, R.; Zhang, H.; Gao, S. Thiacalix[4]arene-supported planar Ln(4) (Ln = Tb(Ⅲ), Dy(Ⅲ)) clusters: toward luminescent and magnetic bifunctional materials. Inorg. Chem. 2009, 48, 11743–11747. doi: 10.1021/ic9017807
12. [12]
  Kajiwara, T.; Kobashi, T.; Shinagawa, R.; Ito, T.; Takaishi, S.; Yamashita, M.; Iki, N. Highly symmetrical tetranuclear cluster complexes supported by p-tert-butylsulfonylcalix[4]arene as a cluster-forming ligand. Eur. J. Inorg. Chem. 2006, 1765–1770.
13. [13]
  Dai, F. R.; Wang, Z. Modular assembly of metal-organic supercontainers incorporating sulfonylcalixarenes. J. Am. Chem. Soc. 2012, 134, 8002–8005. doi: 10.1021/ja300095j
14. [14]
  Du, S.; Hu, C.; Xiao, J. C.; Tan, H.; Liao, W. A giant coordination cage based on sulfonylcalix[4]arenes. Chem. Commun. 2012, 48, 9177–9179. doi: 10.1039/c2cc34265k
15. [15]
  Du, S.; Yu, T. Q.; Liao, W.; Hu, C. Structure modeling, synthesis and X-ray diffraction determination of an extra-large calixarene-based coordination cage and its application in drug delivery. Dalton Trans. 2015, 44, 14394–14402. doi: 10.1039/C5DT01526J
16. [16]
  Fang, Y.; Li, J.; Togo, T.; Jin, F.; Xiao, Z.; Liu, L.; Drake, H.; Lian, X.; Zhou, H. C. Ultra-small face-centered-cubic Ru nanoparticles confined within a porous coordination cage for dehydrogenation. Chem. 2018, 4, 555–563. doi: 10.1016/j.chempr.2018.01.004
17. [17]
  Fang, Y.; Xiao, Z.; Li, J.; Lollar, C.; Liu, L.; Lian, X.; Yuan, S.; Banerjee, S.; Zhang, P.; Zhou, H. C. Formation of a highly reactive cobalt nanocluster crystal within a highly negatively charged porous coordination cage. Angew. Chem. Int. Ed. 2018, 57, 5283–5287. doi: 10.1002/anie.201712372
18. [18]
  Fang, Y.; Xiao, Z.; Kirchon, A.; Li, J.; Jin, F.; Togo, T.; Zhang, L.; Zhu, C.; Zhou, H. C. Bimolecular proximity of a ruthenium complex and methylene blue within an anionic porous coordination cage for enhancing photocatalytic activity. Chem. Sci. 2019, 10, 3529–3534. doi: 10.1039/C8SC05315D
19. [19]
  Fang, Y.; Lian, X.; Huang, Y.; Fu, G.; Xiao, Z.; Wang, Q.; Nan, B.; Pellois, J. P.; Zhou, H. C. Investigating subcellular compartment targeting effect of porous coordination cages for enhancing cancer nanotherapy. Small 2018, 14, e1802709. doi: 10.1002/smll.201802709
20. [20]
  Gong, W.; Chu, D.; Jiang, H.; Chen, X.; Cui, Y.; Liu, Y. Permanent porous hydrogen-bonded frameworks with two types of Bronsted acid sites for heterogeneous asymmetric catalysis. Nat. Commun. 2019, 10, 600. doi: 10.1038/s41467-019-08416-6
21. [21]
  Dai, F. R.; Sambasivam, U.; Hammerstrom, A. J.; Wang, Z. Synthetic supercontainers exhibit distinct solution versus solid state guest-binding behavior. J. Am. Chem. Soc. 2014, 136, 7480–7491. doi: 10.1021/ja502839b
22. [22]
  Tan, C.; Jiao, J.; Li, Z.; Liu, Y.; Han, X.; Cui, Y. Design and assembly of a chiral metallosalen-based octahedral coordination cage for supramolecular asymmetric catalysis. Angew. Chem. Int. Ed. 2018, 57, 2085–2090. doi: 10.1002/anie.201711310
23. [23]
  Dai, F. R.; Becht, D. C.; Wang, Z. Modulating guest binding in sulfonylcalixarene-based metal-organic supercontainers. Chem. Commun. 2014, 50, 5385–5387. doi: 10.1039/C3CC47420H
24. [24]
  Sun, C. Z.; Cheng, L. J.; Qiao, Y.; Zhang, L. Y.; Chen, Z. N.; Dai, F. R.; Lin, W.; Wang, Z. Stimuli-responsive metal-organic supercontainers as synthetic proton receptors. Dalton Trans. 2018, 47, 10256–10263. doi: 10.1039/C8DT01900B
25. [25]
  Zhang, G.; Zhu, X.; Liu, M.; Liao, W. A window frame-like square constructed by bridging Co₄-(TC4A-SO₂) SBUs with 1, 3-bis(2H-tertazol-5-yl)benzene. J. Mol. Struct. 2018, 1151, 29–33. doi: 10.1016/j.molstruc.2017.09.024
26. [26]
  Dai, F. R.; Qiao, Y.; Wang, Z. Designing structurally tunable and functionally versatile synthetic supercontainers. Inorg. Chem. Front. 2016, 3, 243–249.
27. [27]
  Qiao, Y.; Zhang, L.; Li, J.; Lin, W.; Wang, Z. Switching on supramolecular catalysis via cavity mediation and electrostatic regulation. Angew. Chem. Int. Ed. 2016, 55, 12778–12782. doi: 10.1002/anie.201606847
28. [28]
  Cheng, L. J.; Fan, X. X.; Li, Y. P.; Wei, Q. H.; Dai, F. R.; Chen, Z. N.; Wang, Z. Engineering solid-state porosity of synthetic supercontainers via modification of exo-cavities. Inorg. Chem. Commun. 2017, 78, 61–64. doi: 10.1016/j.inoche.2017.03.005
29. [29]
  Sun, C. Z.; Sheng, T. P.; Dai, F. R.; Chen, Z. N. Sulfonylcalixaren-based ortho-dicarboxylate-bridged coordination containers for guest encapsulation and separation. Cryst. Growth Des. 2019, 19, 1144–1148. doi: 10.1021/acs.cgd.8b01633
30. [30]
  Bhuvaneswari, N.; Annamalai, K. P.; Dai, F. R.; Chen, Z. N. Pyridinium functionalized coordination containers as highly efficient electrocatalysts for sustainable oxygen evolution. J. Mater. Chem. A 2017, 5, 23559–23565. doi: 10.1039/C7TA05797K
31. [31]
  Bhuvaneswari, N.; Dai, F. R.; Chen, Z. N. Sensitive and specific guest recognition through pyridinium-modification in spindle-like coordination containers. Chem. Eur. J. 2018, 24, 6580–6585. doi: 10.1002/chem.201705210
32. [32]
  Wang, S.; Gao, X.; Hang, X.; Zhu, X.; Han, H.; Liao, W.; Chen, W. Ultrafine Pt nanoclusters confined in a calixarene-based {Ni₂₄} coordination cage for high-efficient hydrogen evolution reaction. J. Am. Chem. Soc. 2016, 138, 16236–16239. doi: 10.1021/jacs.6b11218
33. [33]
  Liu, M.; Liao, W. P.; Hu, C. H.; Du, S. C.; Zhang, H. J. Calixarene-based nanoscale coordination cages. Angew. Chem. Int. Ed. 2012, 51, 1585–1588. doi: 10.1002/anie.201106732
34. [34]
  Xiong, K.; Jiang, F.; Gai, Y.; Yuan, D.; Chen, L.; Wu, M.; Su, K.; Hong, M. Truncated octahedral coordination cage incorporating six tetranuclear-metal building blocks and twelve linear edges. Chem. Sci. 2012, 3, 2321–2325. doi: 10.1039/c2sc20264f
35. [35]
  Bi, Y.; Wang, S.; Liu, M.; Du, S.; Liao, W. A tetragonal prismatic {Co₃₂} nanocage based on thiacalixarene. Chem. Commun. 2013, 49, 6785–6787. doi: 10.1039/c3cc43347a
36. [36]
  Hang, X.; Liu, B.; Zhu, X.; Wang, S.; Han, H.; Liao, W.; Liu, Y.; Hu, C. Discrete {Ni₄₀} coordination cage: a calixarene-based Johnson-type (J₁₇) hexadecahedron. J. Am. Chem. Soc. 2016, 138, 2969–2972. doi: 10.1021/jacs.6b00695
37. [37]
  Geng, D.; Han, X.; Bi, Y.; Qin, Y.; Li, Q.; Huang, L.; Zhou, K.; Song, L.; Zheng, Z. Merohedral icosahedral M₄₈ (M = Co^Ⅱ, Ni^Ⅱ) cage clusters supported by thiacalix[4]arene. Chem. Sci. 2018, 9, 8535–8541. doi: 10.1039/C8SC03193B
38. [38]
  Su, K.; Jiang, F.; Qian, J.; Wu, M.; Gai, Y.; Pan, J.; Yuan, D.; Hong, M. Open pentameric calixarene nanocage. Inorg. Chem. 2013, 53, 18–20.
39. [39]
  Wang, S.; Gao, X.; Hang, X.; Zhu, X.; Han, H.; Li, X.; Liao, W.; Chen, W. Calixarene-based {Ni₁₈} coordination wheel: highly efficient electrocatalyst for the glucose oxidation and template for the homogenous cluster fabrication. J. Am. Chem. Soc. 2018, 140, 6271–6277. doi: 10.1021/jacs.7b13193
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