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Communication | Open Access

Polyoxometalatocrown ether: A new type of metallacrown ether based on polyoxometalate

Fengping Xiao1,2 ( )Xianggao Meng1Longsheng Wang2,3Jian Hao2Chunlin Lv2Yongge Wei2 ( )
College of Chemistry, Central China Normal University, Wuhan 430079, China
Key Lab of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China
School of Material and Chemical Engineering, Hubei University of Technology, Wuhan 430068, China
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Abstract

Using chain-like polyethers consisting of two terminal –NH2 groups and (TBA)4[α-Mo8O26] as starting materials, two polyoxometalatocrown ethers were prepared by a cyclization reaction through the formation of Mo≡N triple bonds: (TBA)2[Mo6O17N(o-C6H4OCH2(CH2OCH2)nCH2OC6H4-o)N] (compounds 1, n = 1; 2, n = 2). As confirmed by single-crystal X-ray diffraction and infrared (IR) studies, the polyoxometalatocrown ether 2 can capture primary ammonium cations in solid state.

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References

[1]

Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 1967, 89, 2495–2496.

[2]

Pedersen, C. J. Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 1967, 89, 7017–7036.

[3]
Crown Compounds: Toward Future Applications; Cooper, S. R., Ed.; VCH: New York, 1992.
[4]
Gokel, G. W.; Negin, S.; Cantwell, R. Crown ethers. In Comprehensive Supramolecular Chemistry II; Atwood, J. L., Ed.; Elsevier: Amsterdam, 2017; pp 3–48.
[5]

Wang, L.; Cheng, L.; Li, G. F.; Liu, K.; Zhang, Z. M.; Li, P. T.; Dong, S. Y.; Yu, W.; Huang, F. H.; Yan, X. Z. A self-cross-linking supramolecular polymer network enabled by crown-ether-based molecular recognition. J. Am. Chem. Soc. 2020, 142, 2051–2058.

[6]

Hyde, C. B.; Welham, K. J.; Mascagni, P. The use of crown ethers in peptide chemistry. Part 2. Syntheses of dipeptide complexes with cyclic polyether 18-crown-6 and their derivatisation with DMSO. J. Chem. Soc. Perkin Trans. 2 1989, 2011–2015.

[7]

Mohammadzadeh Kakhki, R. Application of crown ethers as stationary phase in the chromatographic methods. J. Incl. Phenom. Macrocycl. Chem. 2013, 75, 11–22.

[8]

Gokel, G. W.; Leevy, W. M.; Weber, M. E. Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev. 2004, 104, 2723–2750.

[9]

Yu, L.; Li, F. Z.; Wu, J. Y.; Xie, J. Q.; Li, S. Development of the aza-crown ether metal complexes as artificial hydrolase. J. Inorg. Biochem. 2016, 154, 89–102.

[10]

Zhang, Y. F.; Di, F. F.; Li, P. F.; Xiong, R. G. Crown ether host-guest molecular ferroelectrics. Chem.—Eur. J. 2022, 28, e202102990.

[11]

Gray, G. M. Metallacrown ethers: Unique organometallic ligands. Comments Inorg. Chem. 1995, 17, 95–114.

[12]

Ostrowska, M.; Fritsky, I. O.; Gumienna-Kontecka, E.; Pavlishchuk, A. V. Metallacrown-based compounds: Applications in catalysis, luminescence, molecular magnetism, and adsorption. Coord. Chem. Rev 2016, 327–328, 304–332.

[13]

Mezei, G.; Zaleski, C. M.; Pecoraro, V. L. Structural and functional evolution of metallacrowns. Chem. Rev. 2007, 107, 4933–5003.

[14]

Slone, R. V.; Benkstein, K. D.; Bélanger, S.; Hupp, J. T.; Guzei, I. A.; Rheingold, A. L. Luminescent transition-metal-containing cyclophanes ("molecular squares"): Covalent self-assembly, host-guest studies and preliminary nanoporous materials applications. Coord. Chem. Rev. 1998, 171, 221–243.

[15]

Leininger, S.; Olenyuk, B.; Stang, P. J. Self-assembly of discrete cyclic nanostructures mediated by transition metals. Chem. Rev. 2000, 100, 853–908.

[16]

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.

[17]

Lah, M. S.; Pecoraro, V. L. Isolation and characterization of {MnII[MnIII(salicylhydroximate)]4(acetate)2(DMF)6}·2DMF: An inorganic analogue of M2+(12-crown-4). J. Am. Chem. Soc. 1989, 111, 7258–7259.

[18]

Powell, J.; Lough, A.; Wang, F. Synthesis and chemistry of a molybdenum carbonyl phosphinite complex containing a ditopic macrocyclic ligand with chelating phosphorus-donor and crown ether characteristics. Organometallics 1992, 11, 2289–2295.

[19]

Kelly, M. E.; Dietrich, A.; Gómez-Ruiz, S.; Kalinowski, B.; Kaluderović, G. N.; Müller, T.; Paschke, R.; Schmidt, J.; Steinborn, D.; Wagner, C. et al. Platinum(IV) metallacrown ethers: Synthesis, structures, host properties and anticancer evaluation. Organometallics 2008, 27, 4917–4927.

[20]

Grosshans, P.; Jouaiti, A.; Hosseini, M. W.; De Cian, A.; Kyritsakas-Gruber, N. Metallacrown ethers: Synthesis and structural investigation of silver metallamacrocycles. Tetrahedron Lett. 2003, 44, 1457–1460.

[21]

Liu, Q. X.; Zhao, X. J.; Wu, X. M.; Guo, J. H.; Wang, X. G. New mercury(II) and silver(I) complexes containing NHC metallacrown ethers with the π-π stacking interactions. J. Organomet. Chem. 2007, 692, 5671–5679.

[22]

Smith, D. C.; Cagle, E. C.; Gray, G. M. Synthesis, characterization and reactions of [RhCl(CO){(Ph2P(CH2CH2O) m CH2CH2Ph2-P,P’)}] n ( m = 3, 4, 5 n = 1, 2 …) metallacrown crown ethers. J. Organomet. Chem. 2018, 876, 78–82.

[23]

Ramakrishna, B.; Kumar, C. A.; Logesh, T. J.; Manimaran, B. Oxamidato pillared heteroligated dirhenium(I) metallacrown ethers: Synthesis, spectroscopic and structural characterization. J. Organomet. Chem. 2017, 828, 116–121.

[24]

Song, F. T.; Ouyang, G. H.; Li, Y.; He, Y. M.; Fan, Q. H. Metallacrown ether catalysts containing phosphine-phosphite polyether ligands for Rh-catalyzed asymmetric hydrogenation-enhancements in activity and enantioselectivity. Eur. J. Org. Chem. 2014, 2014, 6713–6719.

[25]

Gouzerh, P.; Proust, A. Main-group element, organic, and organometallic derivatives of polyoxometalates. Chem. Rev. 1998, 98, 77–112.

[26]

Zhang, H. Y.; Zhao, W. L.; Li, H. Q.; Zhuang, Q. H.; Sun, Z. Q.; Cui, D. Y.; Chen, X. J.; Guo, A.; Ji, X.; An, S. et al. Latest progress in covalently modified polyoxometalates-based molecular assemblies and advanced materials. Polyoxometalates 2022, 1, 9140011.

[27]

Todea, A. M.; Merca, A.; Bögge, H.; Glaser, T.; Pigga, J. M.; Langston, M. L. K.; Liu, T. B.; Prozorov, R.; Luban, M.; Schröder, C. et al. Porous capsules {(M)M5}12FeIII30 (M = MoVI, WVI): Sphere surface supramolecular chemistry with 20 ammonium ions, related solution properties, and tuning of magnetic exchange interactions. Angew. Chem., Int. Ed. 2010, 49, 514–519.

[28]

Long, D. L.; Abbas, H.; Kögerler, P.; Cronin, L. A high-nuclearity “Celtic-ring” isopolyoxotungstate, [H12W36O120]12–, that captures trace potassium ions. J. Am. Chem. Soc. 2004, 126, 13880–13881.

[29]

Xiao, F. P.; Hao, J.; Zhang, J.; Lv, C. L.; Yin, P. C.; Wang, L. S.; Wei, Y. G. Polyoxometalatocyclophanes: Controlled assembly of polyoxometalate-based chiral metallamacrocycles from achiral building blocks. J. Am. Chem. Soc. 2010, 132, 5956–5957.

[30]

Du, Y. H.; Rheingold, A. L.; Maatta, E. A. A polyoxometalate incorporating an organoimido ligand: Preparation and structure of [Mo5O18(MoNC6H4CH3)]2–. J. Am. Chem. Soc. 1992, 114, 345–346.

[31]

Strong, J. B.; Yap, G. P. A.; Ostrander, R.; Liable-Sands, L. M.; Rheingold, A. L.; Thouvenot, R.; Gouzerh, P.; Maatta, E. A. A new class of functionalized polyoxometalates: Synthetic, structural, spectroscopic, and electrochemical studies of organoimido derivatives of [Mo6O19]2–. J. Am. Chem. Soc. 2000, 122, 639–649.

[32]

Proust, A.; Thouvenot, R.; Chaussade, M.; Robert, F.; Gouzerh, P. Phenylimido derivatives of [Mo6O19]2–: Syntheses, X-ray structures, vibrational, electrochemical, 95Mo and 14N NMR studies. Inorg. Chim. Acta 1994, 224, 81–95.

[33]

Wei, Y. G.; Xu, B. B.; Barnes, C. L.; Peng, Z. H. An efficient and convenient reaction protocol to organoimido derivatives of polyoxometalates. J. Am. Chem. Soc. 2001, 123, 4083–4084.

[34]

Akutagawa, T.; Endo, D.; Noro, S. I.; Cronin, L.; Nakamura, T. Directing organic-inorganic hybrid molecular-assemblies of polyoxometalate crown-ether complexes with supramolecular cations. Coord. Chem. Rev. 2007, 251, 2547–2561.

[35]

You, W. S.; Wang, E. B.; He, Q. L.; Xu, L.; Xing, Y.; Jia, H. Q. Synthesis and crystal structure of a new supermolecular compound: [C12H24O6][H3PMo12O40]·22H2O (C12H24O6 = 18-crown-6). J. Mol. Struct. 2000, 524, 133–139.

[36]

Xiong, J.; Luo, T.; Zhang, J.; Li, X. X.; Lv, S. F.; Peng, J. J.; Li, M.; Li, W.; Nakamura, T. Two supramolecular inorganic-organic hybrid crystals based on Keggin polyoxometalates and crown ethers. Crystals. 2018, 8, 17.

[37]

Yang, G.; Wu, Y. C.; Lv, Z. X.; Jiang, X. Y.; Shi, J. H.; Zhang, Y. Z.; Chen, M.; Ni, L. B.; Diao, G. W.; Wei, Y. G. Keggin-type polyoxometalate-based crown ether complex for lithium-sulfur batteries. Chem. Commun. 2023, 59, 788–791.

[38]

Shi, J. H.; Zhang, H. X.; Wang, P. S.; Wang, P.; Zha, J. J.; Liu, Y.; Gautam, J.; Zhang, L. N.; Wang, Y.; Xie, J. et al. Inorganic-organic hybrid supramolecular architectures based on Keggin polyoxometalates and crown ether: Synthesis, crystal structure and electrochemical properties. CrystEngComm 2021, 23, 8482–8489.

[39]

Wang, P.; Zhang, H. X.; Wang, P. S.; Zha, J. J.; Gautam, J.; Zhang, H. Z.; Li, R.; Zhang, L. N.; Diao, G. W.; Ni, L. B. A crown ether supramolecular host-guest complex with Keggin polyoxometalate: Synthesis, crystal structure and electrocatalytic performance for hydrogen evolution reaction. Catal. Commun. 2022, 165, 106446.

[40]

Clegg, W.; Errington, R. J.; Fraser, K. A.; Holmes, S. A.; Schäfer, A. Functionalisation of [Mo6O19]2– with aromatic amines: Synthesis and structure of a hexamolybdate building block with linear difunctionality. J. Chem. Soc. Chem. Commun. 1995, 455–456.

[41]

Stark, J. L.; Rheingold, A. L.; Maatta, E. A. Polyoxometalate clusters as building blocks: Preparation and structure of bis(hexamolybdate) complexes covalently bridged by organodiimido ligands. J. Chem. Soc. Chem. Commun 1995, 1165–1166.

[42]

Roesner, R. A.; McGrath, S. C.; Brockman, J. T.; Moll, J. D.; West, D. X.; Swearingen, J. K.; Castineiras, A. Mono- and di-functional aromatic amines with p-alkoxy substituents as novel arylimido ligands for the hexamolybdate ion. Inorg. Chim. Acta. 2003, 342, 37–47.

[43]

Wu, P. F.; Li, Q.; Ge, N.; Wei, Y. G.; Wang, Y.; Wang, P.; Guo, H. Y. An easy route to monofunctionalized organoimido derivatives of the lindqvist hexamolybdate. Eur. J. Inorg. Chem. 2004, 2004, 2819–2822.

[44]

Xiao, F. P.; Misdrahi, M. F.; Zhang, J.; Yin, P. C.; Hao, J.; Lv, C. L.; Xiao, Z. C.; Liu, T. B.; Wei, Y. G. Buildup of amphiphilic molecular bola from organic-inorganic hybrid polyoxometalates and their vesicle-like supramolecular assembly. Chem.—Eur. J. 2011, 17, 12006–12009.

[45]

Zhang, J.; Xiao, F. P.; Hao, J.; Wei, Y. G. The chemistry of organoimido derivatives of polyoxometalates. Dalton Trans. 2012, 41, 3599–3615.

[46]

Leigh, D. A.; Thomson, A. R. Switchable dual binding mode molecular shuttle. Org. Lett. 2006, 8, 5377–5379.

[47]

Corra, S.; de Vet, C.; Groppi, J.; La Rosa, M.; Silvi, S.; Baroncini, M.; Credi. A. Chemical on/off switching of mechanically planar chirality and chiral anion recognition in a [2]rotaxane molecular shuttle. J. Am. Chem. Soc. 2019, 141, 9129–9133.

Polyoxometalates
Article number: 9140055
Cite this article:
Xiao F, Meng X, Wang L, et al. Polyoxometalatocrown ether: A new type of metallacrown ether based on polyoxometalate. Polyoxometalates, 2024, 3(2): 9140055. https://doi.org/10.26599/POM.2024.9140055

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Received: 26 October 2023
Revised: 23 December 2023
Accepted: 08 January 2024
Published: 19 January 2024
© The Author(s) 2024. Published by Tsinghua University Press.

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