Abstract
A novel and highly soluble bis(hydrazone) was synthesized and characterized by different spectroscopic means. This compound was used as a ditopic ligand for the self-assembly of a grid-like complex using Zn2+ as metal cation. The structure of this compound was fully confirmed by NMR (1D and 2D). The electronic and electrochemical properties were studied using cyclic voltammetry, Osteryoung square wave voltammetry, and UV-Vis spectroscopy. The present work highlights the use of NMR spectroscopy as a tool to describe and analyse the formation of grid-like complexes based on the rotation of the phenyl group attached to the pyrimidine ring. Furthermore, the electrochemical results showed that the bis(hydrazone) 3 exhibits several different redox processes that are affected by the interaction with the metal cation as observed for the grid-like complex. Although the electrochemical processes are all irreversible, this article aims to be an initial study in the search for supramolecular complexes that can be used as electrochemical switches. © 2019. Acad. Colomb. Cienc. Ex. Fis. Nat.
References
Adenier, A., Chehimi, M. M., Gallardo, I., Pinson, J., Vilà, N. (2004). Electrochemical oxidation of aliphatic amines and their attachment to carbon and metal surfaces. Langmuir. 20 (19): 8243-8253. Doi: 10.1021/la049194c
Alam, M. S., Strömsdörfer, S., Dremov, V., Müller, P., Kortus, J., Ruben, M., Lehn, J.-M. (2005). Addressing the Metal Centers of [2×2] CoII4 Grid-Type Complexes by STM/STS. Angewandte Chemie International Edition. 44 (48):7896-7900. Doi:10.1002/anie.200502743
Barboiu, M., Ruben, M., Blasen, G., Kyritsakas, N., Chacko, E., Dutta, M., … Lehn, J.-M. (2006). Self-Assembly, Structure and Solution Dynamics of Tetranuclear Zn2+Hydrazone [2×2] Grid-Type Complexes. European Journal of Inorganic Chemistry. 2006 (4): 784-792. Doi: 10.1002/ejic.200500963
Biswas, S., Das, S., van Leusen, J., Kögerler, P., Chandrasekhar, V. (2014). Tetranuclear [2×2] Square-Grid Lanthanide(III) Complexes: Syntheses, Structures, and Magnetic Properties. European Journal of Inorganic Chemistry. 2014 (25):4159-4167. Doi: 10.1002/ejic.201402326.
Breuning, E., Ruben, M., Lehn, J., Renz, F., García, Y., Ksenofontov, V., … Rissanen, K. (2000). Spin Crossover in a Supramolecular Fe4II [2×2] Grid Triggered by Temperature, Pressure, and Light. Angewandte Chemie International Edition. 39 (14): 2504-2507.Doi: 10.1002/1521-3773(20000717)39:14<2504::AIDANIE2504>3.0.CO;2-B
Bu, X.-H., Tanaka, K., Shionoya, M., Biradha, K., Morishita, H., Furusho, S. (2000). A spontaneously resolved chiral molecular box: A cyclic tetranuclear ZnII complex with DPTZ (DPTZ = 3,6-di-2-pyridyl-1,2,4,5-tetrazine). Chemical Communications. VOL. (2000) (11): 971-972. Doi:10.1039/a909742b
Busch, D. H. (1967). Transition Metal Complexes of the new Synthetic Macrocyclic Ligands. Helvetica Chimica Acta. 50 (S1): 174-206. Doi: 10.1002/hlca.19670500914
Campos-Fernández, C. S., Clérac, R., Koomen, J. M., Russell, D. H., Dunbar, K. R. (2001). Fine-Tuning the Ring-Size of Metallacyclophanes: A Rational Approach to Molecular Pentagons. Journal of the American Chemical Society. 123(4): 773-774. Doi: 10.1021/ja002960r
Carmona-Vargas, C. C., Váquiro, I. Y., Jaramillo-Gómez, L. M., Lehn, J.-M., Chaur, M. N. (2017). Grid-type complexes of M 2+ (M = Co, Ni, and Zn) with highly soluble bis(hydrazone)thiopyrimidine-based ligands: Spectroscopy and electrochemical properties. Inorganica Chimica Acta. 468: 131-139. Doi:10.1016/j.ica.2017.05.002
Chaur-Valencia, M. N., Zuluaga Corrales, H. F., Martínez, G. (2018). Electronic and electrochemical properties of gridtype metal ion complexes (Fe+2 and Co2+) with a pyridinepyrimidine-pyridine based bis(hydrazone). Revista Colombiana de Química. 47 (2): 45-53. Doi: 10.15446/rev.colomb.quim.v47n2.66081
Curtis, N. F. (1960). Transition-metal complexes with aliphatic Schiff bases. Part I. Nickel(II) complexes with N-isopropylideneethylenediamine schiff bases. Journal of the Chemical Society (Resumed). 4409-40413. Doi:10.1039/jr9600004409
Dawe, L. N., Shuvaev, K. V., Thompson, L. K. (2009). Polytopic ligand directed self-assembly—polymetallic [n×n] grids versus non-grid oligomers. Chemical Society Reviews. 38 (8): 2334. Doi: 10.1039/b807219c
Dawe, L. N. & Thompson, L. K. (2008). Complete and ‘incomplete’ [2 × 2] grids by self-assembly with a sterically hindered ditopic imidazole hydrazone ligand—structural and magnetic studies. Dalton Transactions. 27: 3610. Doi:10.1039/b800529j
Dietrich-Buchecker, C. O. & Sauvage, J.-P. (1989). A Synthetic Molecular Trefoil Knot. Angewandte Chemie International Edition in English. 28 (2): 189-192. Doi: 10.1002/anie.198901891
Dutta, M., Movassat, M., Brook, D. J. R., Oliver, A., Ward, D. (2011). Molecular motion in zinc hydrazone grid complexes. Supramolecular Chemistry. 23 (9): 632-643. Doi: 10.1080/10610278.2011.593626
Fernández, M. A., Barona, J. C., Polo-Cerón, D., Chaur, M. N. (2015). Estudios fotoquímicos y electroquímicos de complejos lantánidos de 6-(hidroximetil)piridin- 2-carboxaldehído [2-metilpirimidina-4,6-diil] bishidrazona. Revista Colombiana de Química. 43 (1): 5-11. Doi: 10.15446/rev.colomb. quim.v43n1.50540
García, A. M., Romero-Salguero, F. J., Bassani, D. M., Lehn, J. M., Baum, G., Fenske, D. (1999). Selfassembly and characterization of multimetallic gridtype lead(II) complexes. Chemistry - A European
Journal. 5 (6): 1803-1808. Doi: 10.1002/(SICI)1521-3765(19990604)5:6<1803::AID-CHEM1803>3.0.CO;2-M
Gordillo, M. A., Soto-Monsalve, M., Carmona-Vargas, C. C., Gutiérrez, G., D’Vries, R. F., Lehn, J. M., Chaur, M. N. (2017). Photochemical and Electrochemical Triggered Bis(hydrazone) Switch. Chemistry - A European Journal. 23 (59): 14872-14882. Doi: 10.1002/chem.201703065
Hanan, G. S., Volkmer, D., Schubert, U. S., Lehn, J. M., Baum, G., Fenske, D. (1997). Coordination arrays: Tetranuclear cobalt(II) complexes with [2 x 2]-grid structure. Angewandte Chemie - International Edition in English. 36 (17): 1842-1844. Doi: 10.1002/anie.199718421
Hardy, J. G. (2013). Metallosupramolecular grid complexes: Towards nanostructured materials with high-tech applications. Chemical Society Reviews. 42 (19): 7881. Doi:10.1039/c3cs60061k
Harrowfield, J. & Lehn, J. (2012). ChemInform Abstract: Multifunctionality and Multivalency Generation by Selfassembly of Grid-type Metallosupramolecular Architectures. ChemInform. 43 (28): 170-173. Doi: 10.1002/chin.201228260
Hasenknopf, B., Lehn, J. M., Boumediene, N., Dupont-Gervais, A., Van Dorsselaer, A., Kneisel, B., Fenske, D. (1997).
Self-assembly of tetra- and hexanuclear circular helicates. Journal of the American Chemical Society. 119 (45):10956-10962. Doi: 10.1021/ja971204r
Lehn, J.-M. (1988). Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices(Nobel Lecture). Angewandte Chemie International Edition in English. 27 (1): 89-112. Doi: 10.1002/anie.198800891
Lehn, J.-M. (2006). Molecular and Supramolecular Devices. Supramolecular Chemistry. p. 89-138. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA. Doi: 10.1002/3527607439.ch8
Nobelprize.org. (2016). The Nobel Prize in Chemistry 2016 - Advanced Information. Accessed on: December 20, 2018. Available from:https://www.nobelprize.org/prizes/chemistry/2016/advanced-information/
Parween, A., Naskar, S., Mota, A. J., Espinosa Ferao, A., Chattopadhyay, S. K., Rivière, E., … Naskar, S. (2017). C i -Symmetry, [2 × 2] grid, square copper complex with the N 4, N 5 -bis(4-fluorophenyl)-1H-imidazole-4,5-dicarboxamide ligand: Structure, catecholase activity, magnetic properties and DFT calculations. New Journal of Chemistry. 41 (20):11750-11758. Doi: 10.1039/C7NJ01667K
Rojo, Z., Romero-Salguero, F.-J., Lehn, J.-M., Baum, G., Fenske, D. (1999). Self-Assembly, Structure, and Physical Properties of Tetranuclear ZnII and CoII Complexes of [2 x 2] Grid-Type. European Journal of Inorganic Chemistry. 1999: 1421-1428. Doi: 10.1002/(SICI)1099-0682(199909)1999:9%3C1421::AIDEJIC1421%3E3.0.CO;2-J
Ruben, M., Breuning, E., Gisselbrecht, J. P., Lehn, J. M. (2000). Multilevel molecular electronic species: Electrochemical reduction of a [2 x 2] Co4/(II) grid-type complex by 11 electrons in 10 reversible steps. AngewandteChemie - International Edition. 39 (22): 4139-4142. Doi: 10.1002/1521-3773(20001117)39:22<4139::AIDANIE4139>3.0.CO;2-Y
Ruben, M., Breuning, E., Lehn, J.-M., Ksenofontov, V., Renz, F., Gütlich, P., Vaughan, G. B. M. (2003). Supramolecular Spintronic Devices: Spin Transitions and Magnetostructural Correlations in[Fe4IIL4]8+[2×2]-Grid-Type Complexes. Chemistry - A European Journal. 9 (18): 4422-4429. Doi:10.1002/chem.200304933
Ruben, M., Lehn, J.-M., Müller, P. (2006). Addressing metal centres in supramolecular assemblies. Chem. Soc. Rev. 35 (11): 1056-1067. Doi: 10.1039/B517267P
Ruben, M., Lehn, J., Vaughan, G. (2003). Synthesis of ionisable [2 × 2] grid-type metallo-arrays and reversible protonic modulation of the optical properties of the [CoII4L 4 ] 8+species. Chem. Commun. 3 (12): 1338-1339. Doi: 10.1039/B303922F
Ruben, M., Rojo, J., Romero-Salguero, F. J., Uppadine, L. H., Lehn, J.-M. (2004). Grid-Type Metal Ion Architectures: Functional Metallosupramolecular Arrays. Angewandte Chemie International Edition. 43 (28): 3644-3662. Doi: 10.1002/anie.200300636
Shen, F., Huang, W., Wu, D., Zheng, Z., Huang, X.-C., Sato, O. (2016). Redox Modulation of Spin Crossover within a Cobalt Metallogrid. Inorganic Chemistry. 55 (2): 902-908. Doi: 10.1021/acs.inorgchem.5b02442
Stadler, A.-M., Ramírez, J., Lehn, J.-M., Vincent, B. (2016). Supramolecular reactions of metallo-architectures: Ag 2 -double-helicate/Zn 4 -grid, Pb 4 -grid/Zn 4 -grid interconversions, and Ag 2 -double-helicate fusion. Chemical Science. 7 (6): 3689-3693. Doi: 10.1039/C5SC04403K
Stadler, A. M., Kyritsakas, N., Graff, R., Lehn, J. M. (2006). Formation of rack- And grid-type metallosupramolecular architectures and generation of molecular motion by reversible uncoiling of helical ligand strands. Chemistry - A European Journal. 12 (17): 4503-4522. Doi: 10.1002/chem.200501202
Stefankiewicz, A. R., Harrowfield, J., Madalan, A. M., Lehn, J.-M. (2013). Tuning the planarity of [2 × 2] grids. CrystEngComm. 15 (44): 9128. Doi: 10.1039/c3ce41510d
Stefankiewicz, A. R., Rogez, G., Harrowfield, J., Drillon, M., Lehn, J.-M. (2009). Structural features directing the specificity and functionality of metallo-supramolecular grid-type architectures. Dalton Transactions. 29: 5787. Doi: 10.1039/b902262g
Stefankiewicz, A. R., Wałęsa-Chorab, M., Szcześniak, H. B., Patroniak, V., Kubicki, M., Hnatejko, Z., Harrowfield, J. (2010). Grid-corner analogues: Synthesis, characterisation and spectroscopic properties of meridional complexes of tridentate NNO Schiff-base ligands. Polyhedron. 29 (1): 178-187. Doi: 10.1016/j.poly.2009.06.069
Thompson, L. K., Waldmann, O., Xu, Z. (2005). Polynuclear manganese grids and clusters - A magnetic perspective. Coordination Chemistry Reviews. 249 (23): 2677-2690. Doi: 10.1016/j.ccr.2005.07.002
Uppadine, L. H., Gisselbrecht, J. P., Kyritsakas, N., Nättinen, K., Rissanen, K., Lehn, J. M. (2005). Mixed-valence, mixed-spin-state, and heterometallic [2×2] grid-type arrays based on heteroditopic hydrazone ligands: Synthesis and electrochemical features. Chemistry - A European Journal. 11 (8): 2549-2565. Doi: 10.1002/chem.200401224
Wang, S., Men, G., Zhao, L., Hou, Q., Jiang, S. (2010). Binaphthyl-derived salicylidene Schiff base for dualchannel sensing of Cu, Zn cations and integrated molecular logic gates. Sensors and Actuators, B: Chemical. 145 (2): 826-831. Doi: 10.1016/j.snb.2010.01.060
Wasserman, E. (1960). the Preparation of Interlocking Rings: a Catenane1. Journal of the American Chemical Society. 82 (16): 4433-4434. Doi: 10.1021/ja01501a082
Wu, S. Q., Wang, Y. T., Cui, A. L., Kou, H. Z. (2014). Toward higher nuclearity: Tetranuclear cobalt(II) metallogrid exhibiting spin crossover. Inorganic Chemistry. 53 (5):2613-2618. Doi: 10.1021/ic402971a
Youinou, M.-T., Rahmouni, N., Fischer, J., Osborn, J. A. (1992). Self-Assembly of a Cu4 Complex with Coplanar Copper(I) Ions: Synthesis, Structure, and Electrochemical Properties. Angewandte Chemie International Edition in English. 31(6): 733-735. Doi: 10.1002/anie.199207331
Yu, F., Hou, L. J., Qin, L. Y., Chao, J. Bin, Wang, Y., Jin, W. J. (2016). A new colorimetric and turn-on fluorescent chemosensor for Al3+ in aqueous medium and its application in live-cell imaging. Journal of Photochemistry and Photobiology A: Chemistry. 315: 8-13. Doi: 10.1016/j.jphotochem.2015.09.006
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