Abstract
New crystalline \(\{\text{Mn}_{2}^{\text{II}}\text{Mn}_{2}^{\text{III}}\}\) tetranuclear cluster is prepared by the interaction of manganese(II) chloride with calix[4]arene 3 functionalized at the upper rim by distal p-(4-nitrophenyl)diazenyl and p-tert-butyl groups displaying different electronic effects and sizes. The structure of the cluster is studied by single-crystal XRD. Due to the presence of (4-nitrophenyl)diazenyl moieties at the upper rim of the macrocyclic ligand, the molecules of the tetranuclear \(\{\text{Mn}_{2}^{\text{II}}\text{Mn}_{2}^{\text{III}}\}\) clusters are involved in π-stacking interactions leading to the formation of 2D supramolecular layers affording a porous crystal packing.
REFERENCES
A. Zabala-Lekuona, J. Manuel Seco, and E. Colacio. Single-molecule magnets: From Mn12-ac to dysprosium metallocenes, a travel in time. Coord. Chem. Rev., 2021, 441, 213984. https://doi.org/10.1016/j.ccr.2021.213984
E. Moreno-Pineda and W. Wernsdorfer. Measuring molecular magnets for quantum technologies. Nat. Rev. Phys., 2021, 3, 645. https://doi.org/10.1038/s42254-021-00340-3
S. M. Aldoshin, D. V. Korchagin, A. V. Palii, and B. S. Tsukerblat. Some new trends in the design of single molecule magnets. Pure Appl. Chem., 2017, 89(8), 1119. https://doi.org/10.1515/pac-2017-0103
C. D. Gutsche, M. Iqbal, and D. Stewart. Calixarenes. 19. Syntheses procedures for p-tert-butylcalix[4]arene. J. Org. Chem., 1986, 51(5), 742-745. https://doi.org/10.1021/jo00355a033
A. Ovsyannikov, S. Solovieva, I. Antipin, and S. Ferlay. Coordination polymers based on calixarene derivatives: Structures and properties. Coord. Chem. Rev., 2017, 352, 151-186. https://doi.org/10.1016/j.ccr.2017.09.004
R. O. Fuller, G. A. Koutsantonis, and M. I. Ogden. Magnetic properties of calixarene-supported metal coordination clusters. Coord. Chem. Rev., 2020, 402, 213066. https://doi.org/10.1016/j.ccr.2019.213066
A. S. Ovsyannikov, I. V. Khariushin, S. E. Solovieva, I. S. Antipin, H. Komiya, N. Marets, H. Tanaka, H. Ohmagari, M. Hasegawa, J. J. Zakrzewski, S. Chorazy, N. Kyritsakas, M. W. Hosseini, and S. Ferlay. Mixed Tb/Dy coordination ladders based on tetra(carboxymethyl)thiacalix[4]arene: A new avenue towards luminescent molecular nanomagnets. RSC Adv., 2020, 10, 11755. https://doi.org/10.1039/D0RA01263G
S. M. Taylor, G. Karotsis, R. D. McIntosh, S. Kennedy, S. J. Teat, C. M. Beavers, W. Wernsdorfer, S. Piligkos, S. J. Dalgarno, and E. K. Brechin. A family of calix[4]arene-supported [Mn(III)2Mn(II)2] clusters. Chem. - Eur. J., 2011, 17, 7521. https://doi.org/10.1002/chem.201003327
S. M. Aldoshin, I. S. Antipin, V. I. Ovcharenko, S. E. Solov′eva, A. S. Bogomyakov, D. V. Korchagin, G. V. Shilov, E. A. Yur′eva, F. B. Mushenok, K. V. Bozhenko, and A. N. Utenyshev. Synthesis, structure, and properties of a new representative of the family of calix[4]arene-containing [MnII2MnIII2]-clusters. Russ. Chem. Bull., 2013, 62, 536. https://doi.org/10.1007/s11172-013-0074-5
S. M. Aldoshin, I. S. Antipin, S. E. Solov′eva, N. A. Sanina, D. V. Korchagin, G. V. Shilov, F. B. Mushenok, A. N. Utenyshev, and K. V. Bozhenko. Experimental and theoretical study of the influence of peripheral environment on magnetic properties of tetranuclear manganese skeleton in new representatives of calix[4]arene-containing [MnII2 MnIII2] clusters. J. Mol. Struct., 2015, 1081, 217. https://doi.org/10.1016/j.molstruc.2014.10.022
M. A. Palacios, R. McLellan, C. M. Beavers, S. J. Teat, H. Weihe, S. Piligkos, S. J. Dalgarno, and E. K. Brechin. Facile interchange of 3d and ions in single-molecule magnets: Stepwise assembly of [Mn4], [Mn3Ln] and [Mn2Ln2] cages within calix[4]arene scaffolds. Chem. - Eur. J., 2015, 21, 11212. https://doi.org/10.1002/chem.201500001
A. S. Ovsyannikov, I. V. Strelnikova, I. D. Shutilov, D. R. Islamov, P. V. Dorovatovskii, A. T. Gubaidullin, A. S. Agarkov, S. E. Solovieva, and I.S. Antipin. A series of new manganese(II) polynuclear complexes based on nitrothiacalix[4]arenes: The study of interplay between macrocycle platform flexibility and structural diversity of coordination compounds. Crystals, 2023, 13, 1017. https://doi.org/10.3390/cryst13071017
A. S. Ovsyannikov, N. A. Epifanova, E. V. Popova, N. Kyritsakas, S. Ferlay, M. W. Hosseini, S. K. Latypov, S. E. Solovieva, I. S. Antipin, and A. I. Konovalov. Template synthesis of tetrakis-triazolylthiacalix[4]arene in the cone conformation and supramolecular structure of its hexanuclear complex with Ag(I). Macroheterocycles, 2014, 7(2), 189-195. https://doi.org/10.6060/mhc140273s
I. V. Khariushin, A. S. Ovsyannikov, D. R. Islamov, A. I. Samigullina, S. E. Solovieva, J. J. Zakrzewski, S. Chorazy, and S. Ferlay. Tuning crystal packing and magnetic properties in a series of [Dy12] metallocubanes based on azobenzene derivatives of salicylic acid. Inorg. Chem., 2023, 62(27), 10548. https://doi.org/10.1021/acs.inorgchem.3c00433
A. E. Thorarinsdottir and T. D. Harris. Metal–organic framework magnets. Chem. Rev., 2020, 120(16), 8716. https://doi.org/10.1021/acs.chemrev.9b00666
H. G. Becker, W. Berger, and G. Domschke. ORGANIKUM. Organisch-chemisches Grundpraktikum. Berlin, Germany: Deutscher Verlag der Wissenschaften, 1965.
S. Elcin and H. Deligoz. Di-substituted azocalix[4]arenes containing chromogenic groups: Synthesis, characterization, extraction, and thermal behavior. Tetrahedron, 2013, 69(33), 6832. https://doi.org/10.1016/j.tet.2013.06.018
V. A. Lazarenko, P. V. Dorovatovskii, Y. V. Zubavichus, A. S. Burlov, Y. V. Koshchienko, V. G. Vlasenko, and V. N. Khrustalev. High-throughput small-molecule crystallography at the ′Belok′ beamline of the Kurchatov synchrotron radiation source: Transition metal complexes with azomethine ligands as a case study. Crystals, 2017, 7(11), 325. https://doi.org/10.3390/cryst7110325
R. D. Svetogorov, P. V. Dorovatovskii, and V. A. Lazarenko. Belok/XSA diffraction beamline for studying crystalline samples at Kurchatov synchrotron radiation source. Cryst. Res. Technol., 2020, 55(5), 1900184. https://doi.org/10.1002/crat.201900184
W. Kabsch. XDS. Acta Crystallogr., Sect. D: Biol. Crystallogr., 2010, 66(2), 125-132. https://doi.org/10.1107/s0907444909047337
G. M. Sheldrick. SHELXT - Integrated space-group and crystal-structure determination. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71(1), 3-8. https://doi.org/10.1107/s2053273314026370
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. J. Puschmann. OLEX2: a complete structure solution, refinement and analysis program. Appl. Crystallogr., 2009, 42, 339. https://doi.org/10.1107/S0021889808042726
Z. Asfari, A. Bilyk, C. Bond, J. M. Harrowfield, G. A. Koutsantonis, N. Lengkeek, M. Mocerino, B. W. Skelton, A. N. Sobolev, S. Strano, J. Vicens, and A. H. White. Factors influencing solvent adduct formation by calixarenes in the solid state. Org. Biomol. Chem., 2004, 2, 387. https://doi.org/10.1039/B308214H
N. Ehlinger and M. Perrin. Structure of p-tetrakis-(4-nitrophenylazo)calix[4]-arene-4-picoline (1:4) complex. J. Incl. Phenom. Macrocycl. Chem., 1995, 22, 33. https://doi.org/10.1007/BF00706496
C. M. Jin, Z. Wang, K. L. Zhang, G.-Y. Lu, and X.-Z. You. Crystal structure of the molecular adduct of 5-mono[(4-nitrophenyl)azo]-25,26,27,28-tetrahydroxycalix[4]arene with chloroform (1:1). J. Chem. Crystallogr., 2002, 32, 293. https://doi.org/10.1023/A:1020253423983
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This work was funded by the Russian Science Foundation (grant No. 19-73-20035).
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Russian Text © The Author(s), 2024, published in Zhurnal Strukturnoi Khimii, 2024, Vol. 65, No. 2, 122224.https://doi.org/10.26902/JSC_id122224
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Ovsyannikov, A.S., Strelnikova, Y.V., Iova, A.A. et al. Synthesis and Porous Crystal Structure of a New Tetranuclear \(\text{\{Mn}_2^{\text{II}}\text{Mn}_2^{\text{III}}\}\) Cluster Based on a Calix[4]Arene Functionalized at the Upper Rim by Distal p-(4-Nitrophenyl)Diazenyl and p-tert-Butyl Groups. J Struct Chem 65, 313–322 (2024). https://doi.org/10.1134/S0022476624020094
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DOI: https://doi.org/10.1134/S0022476624020094