Анотація
The review is devoted to a new class of complexones – aminocarboxyphosphonic acids and lanthanide metal complexes based on them. Interest in such compounds is due to the specificity of the structure of aminocarboxyphosphonic acids molecules, which contain various functional acid groups (carboxylic and phosphonic) at one main nitrogen atom, which differ significantly in basicity, charge, stereochemistry and size. This provides a wide range of coordination possibilities of ligands, which most fully satisfy the spatial requirements of the complexing ion and allows obtaining polynuclear structures of an unusual structure in the crystalline state. The article summarizes the literature data obtained by various authors regarding the study of the structure and spectral properties of aminocarboxyphosphonates of 4-f metals in solutions and crystals, their thermal properties, structural features, prospects for creating multifunctional technical materials based on them are considered.
Посилання
Stein Sr E.W., Clearfield A., Subramanian M.A. Conductivity of group IV metal sulfophosphonates and a new class of interstratified metal amine-sulfophosphonates. Solid State Ionics. 1996. 83(1–2): 113–124. https://doi.org/10.1016/0167-2738(95)00215-4.
Alberti G., Constantino U. Solid state supramolecular chemistry. (Ed.: J. M. Lehn), Pergamon – Elsevier Science Ltd., London, 1996.
Clearfield A. Recent advances in metal phosphonate chemistry. Current Opinion in Solid State and Materials Science. 1996. 1(2): 268–278.
https://doi.org/10.1016/S1359-0286(96) 80094-5.
Clearfield A. Metal phosphonate chemistry. Progress in inorganic chemistry. 1998. 47: 371–510.
Rosi N.L., Eckert J., Eddaoudi M., Vodak D.T., Kim J., O'Keeffe M., Yaghi O.M. Hydrogen storage in microporous metal-organic frameworks. Science. 2003. 300(5622): 1127–1129. https://doi.org/10.1126/science.1083440.
Eddaoudi M., Kim J., O'Keeffe M., Yaghi O.M. Cu2[o-Br-C6H3(CO2)2]2(H2O)2∙(DMF)8(H2O)2: A Framework Deliberately Designed To Have the NbO Structure Type. Journal of the American Chemical Society. 2002.124(3): 376–377.
https://doi.org/10.1021/ja017154e.
Costantino U., Nocchetti M., Vivani R. (Preparation, characterization, and structure of zirconium fluoride alkylamino-N,N-bismethylphosphonates: A new design for layered zirconium diphosphonates with a poorly hindered interlayer region. Journal of the American Chemical Society. 2002. 124 (28): 8428–8434. https://doi.org/10.1021/ja026124o.
Gutschke S.O., Price D.J., Powell A. K., Wood P.T..Solvothermal Synthesis of the Canted Antiferromagnet {K2[CoO3PCH2N(CH2CO2)2]}6⋅ xH2O. AngewandteChemie International Edition. 1999. 38 (8): 1088–1090.
https://doi.org/10.1002/(SICI)1521-3773 (19990419)38:8<1088::AID-ANIE1088>3.0.CO;2-2.
Gałdecka E., Gałdecki Z., Gawryszewska P., Legendziewicz J. Structure of a novel polynuclear europium compound with N-phosphonomethylglycine: heptaaquaperchloratodi-μ 4-N-phosphonomethylglycine-dieuropium (III) triperchlorate monohydrate, [Eu2(HO3PCH2NH2CH2CO2)2(H2O)7(ClO4)]•3ClO4•H2O. New Journal of Chemistry. 2000. 24(6): 387–391.
https://doi.org/10.1039/B000230P.
Stock N., Frey S.A., Stucky G.D., Cheetham A.K. Synthesis and characterization of two manganese phosphonocarboxylates: Mn3(O3PCH2COO)2 and Mn3(O3PCH2CH2COO)2. Journal of the Chemical Society, Dalton Transactions. 2000. 23: 4292–4296.
https://doi.org/10.1039/B006411O.
Costantino U., Nocchetti M., Vivani R. Preparation, characterization, and structure of zirconium fluoride alkylamino-N,N-bismethylphosphonates: A new design for layered zirconium diphosphonates with a poorly hindered interlayer region. Journal of the American Chemical Society. 2002. 124(28): 8428–8434.
https://doi.org/10.1021/ja026124o.
Lei C., Mao J.G., Sun Y.Q., Zeng H.Y., Clearfield A. {Zn6[MeN (CH2CO2)(CH2PO3)]6(Zn)}4-Anion: The First Example of the Oxo-Bridged Zn6 Octahedron with a Centered Zn (II) Cation. Inorganic chemistry. 2003. 42(20): 6157–6159.
https://doi.org/10.1021/ic034137c.
Song J.L., Mao J.G. Syntheses, crystal structures and characterizations of new zinc(II) and lead(II) carboxylate-phosphonates. Journal of molecular structure. 2005. 740 (1–3): 181–186.
https://doi.org/10.1016/j.molstruc.2005.01.034.
Ying S.M., Mao J.G. Novel layered lead(II) aminodiphosphonates with carboxylate‐sulfonate and 1, 3, 5‐benzenetricarboxylate ligands as pendant groups or intercalated species. European Journal of Inorganic Chemistry. 2004. 2004(6):1270–1276. https://doi.org/10.1002/ejic.200300607.
Song J.L., Lei C., Sun Y.Q., Mao J.G. Syntheses, characterizations and crystal structures of two lead (II) phosphonate–sulfonate hybrid materials. Journal of Solid State Chemistry. 2004. 177 (7): 2557–2564. https://doi.org/10.1016/j.jssc.2004.03.037.
Ptaszynski B., Zwolinska A. Synthesis and properties of solid complexes of lanthanum, cerium, neodymium and erbium with N-phosphonomethylglycine. Polish Journal of Environmental Studies. 2001. 10 (4): 257–262.
Pangunoori R., Ram K. Rare Earth Metal Complexes of N-PhosphonomethylGlycin. Asian J. Chem. 1995.7 (1): 223–229.
Legendziewicz J., Gawryszewska P., Gałdecka E., Gałdecki Z. Novel polynuclear compound of europium with N-phosphonomethylglycine: spectroscopy and structure. Journal of alloys and compounds. 1998. 275: 356–360. https://doi.org/10.1016/S0925-8388(98)00339-9.
Mao J.G. Structures and luminescent properties of lanthanide phosphonates. Coordination chemistry reviews. 2007. 251 (11–12): 1493–1520. https://doi.org/10.1016/j.ccr.2007.02.008.
Tang S.F., Song J.L., Mao J.G. Syntheses, Crystal Structures, and Characterizations of a Series of New Layered Lanthanide Carboxylate‐Phosphonates. Eur. J. Inorg. Chem. 2006. 2006 (10): 2011–2019. https://doi.org/10.1002/ejic.200600039.
Tang S.F., Song J.L., Li X.L., Mao J.G. Luminescent lanthanide (III) carboxylate − phosphonates with helical tunnels. Crystal growth & design. 2006. 6 (10): 2322–2326. https://doi.org/10.1021/cg060248l.
Evans, Christopher H. Biochemistry of the Lanthanides. Vol. 8.Springer Science & Business Media. 2013.
Guzik M., Boulon G., Guyot Y., Tomaszewicz E., Bieza M., Legendziewicz J., ...&Sobota M. Nd3+ Ion as a Structural Probe in Studies of Selected Oxide Host Lattices: Coupling the Low-Temperature High-Resolution Spectroscopic Techniques with Microscopy. In Light-Matter Interactions Towards the Nanoscale. 2022. (P. 175–217). Dordrecht: Springer Netherlands.
Song J.L., Lei C., Mao J.G. Syntheses, Crystal Structures, and Luminescent Properties of Novel Layered Lanthanide Sulfonate − Phosphonates. Inorganic chemistry. 2004. 43 (18): 5630–5634.https://doi.org/10.1021/ic049376u.
Song J.L., Mao J.G. New Types of Blue, Red or Near IR Luminescent Phosphonate‐Decorated Lanthanide Oxalates. Chemistry–A European Journal. 2005. 11 (5): 1417–1424. https://doi.org/10.1002/chem.200400889.
Shkol'nikova L.M., Porai-Koshits M.A. Structure of the uncharged, anionic, and cationic forms of aminoalkylcarboxylic and aminoalkylphosphoniccomplexones. Russian Chemical Reviews. 1990. 59(7): 643–662https://doi.org/10.1070/RC1990v059n07ABEH003548.
Shkol'nikova L.M., Masyuk A.A., Khizbullin F.F. et al. X-ray diffraction structural investigation of organic complexone ligands. XVIII. Crystal and molecular structure of phosphonomethylglycinehemihydrochloride. J Struct Chem. 1991. 31: 768–773. https://doi.org/10.1007/BF00752557.
Meddeb-Limem S., Fredj A.B. Computational study of the dimerization of glyphosate: mechanism and effect of solvent. RSC advances. 2024. 14(32): 23184–23203. https://doi.org/10.1039/D4RA04300F.
Gokila A., Ayyappan S. Quantum chemical insight properties of glyphosine (N,N-Bis (phosphonomethyl) glycine)–a combined hf and density functional study. Digest Journal of Nanomaterials & Biostructures (DJNB). 2021.16(2):535–554. https://doi.org/10.15251/djnb.2021.162.535.
Shovkova G.V., Trunova O.K., Gudima A.O., Mishchenko A.M. Conformational analysis of N-(phosphonomethyl)aminosuccinic acid anions in soils. Ukr. Chem. J. 2017. 83(5): 26–34. [in Ukrainian].
Trunova E.K., Rusakova N.V., Berezhnitskaya A.S., Smola S.S., Snurnikova O.V., Makotrik T.A. Synthesis and spectral-luminescent properties of complexes of lanthanides with phosphonomethyl-aminosuccinic acid. Ukr. Chem. J. 2011. 77 (12):71–77. [in Russian].
Trunova O., Rusakova N. Luminescent properties of Nd (III) complexes with ethylenediamine-N, N'-disuccinic and N,N-bis (phosphonomethyl)-2-aminopropionic acids. Ukrainian Chemistry Journal. 2023. 89 (6): 55–70. https://doi.org/10.33609/2708-129X.89.06.2023.55-70.
Trunova О.К., Mishchenko A.М., Makotryk T.О. Synthesis, spectral characterization and stability of the Nd(III) and Co(II) heterometallic complexes with aminopolycarboxylic acids. Ukr. Chem. J. 2022. 88(2):116–130. https://doi.org/10.33609/2708-129X.88.02.2022.116-130.
Serpaggi F., Férey G. Hybrid Organic− Inorganic Frameworks (MIL-n). Hydrothermal Synthesis of a Series of Pillared Lanthanide Carboxyethylphosphonates and X-ray Powder ab Initio Structure Determination of MIL-19, Pr[O3P(CH2)2CO2]. Inorganic chemistry. 1999. 38(21): 4741–4744. https://doi.org/10.1021/ic981440i.
Serre C., Stock N., Bein T., Férey G. Synthesis and characterization of a new three-dimensional lanthanide carboxyphosphonate: Ln4(H2O)7[O2C−C5H10N−CH2-PO3]4(H2O)5. Inorganic chemistry. 2004. 43(10): 3159–3163. https://doi.org/10.1021/ic035363p.
Seeber G., Pickering A.L., Long D.L., Cronin L. Controlling dimensionality of silver (I) coordination networks with rigid aliphatic amino ligands: from a 2D to a 3D network of unprecedented topology comprising helical channels. Chemical communications. 2000. (16): 2002–2003. https://doi.org/10.1039/B305188A.
Prior T.J., Rosseinsky M. J. Chiral direction and interconnection of helical three-connected networks in metal-organic frameworks. Inorganic chemistry. 2003. 42(5): 1564–1575. https://doi.org/10.1021/ic025775i.
Inoue K., Imai H., Ghalsasi P.S., Kikuchi K., Ohba M., Ōkawa H., Yakhmi J.V. A Three‐Dimensional Ferrimagnet with a High Magnetic Transition Temperature (TC) of 53 K Based on a Chiral Molecule. AngewandteChemie International Edition. 2001. 40(22): 4242–4245.
https://doi.org/10.1002/1521-3773(20011119) 40:22<4242::AID-ANIE4242>3.0.CO;2-H.
Minguet M., Luneau D., Lhotel E., Villar V., Paulsen C., Amabilino D. B., Veciana J. An enantiopure molecular ferromagnet. AngewandteChemie International Edition. 2002. 41(4): 586–589.
Qin C., Xu L., Wei Y., Wang X., Li F. New Vanadium Phosphate {[(phen)VIVO]2 (VV2O5)(HPO4)}n with Chiral Layer Architecture. Inorganic chemistry. 2003. 42(9): 3107–3110. https://doi.org/10.1021/ic026256i.
Bøgevig A., Juhl K., Kumaragurubaran N., Zhuang W., Jørgensen K.A. Direct organo‐catalytic asymmetric α‐amination of aldehydes – a simple approach to optically active α‐amino aldehydes, α‐amino alcohols, and α‐amino acids. AngewandteChemie International Edition. 2002. 41(10): 1790–1793.
https://doi.org/10.1002/1521-3773(20020517) 41:10<1790::AID-ANIE1790>3.0.CO;2-Y.
Duthaler R.O. Proline‐Catalyzed Asymmetric α‐Amination of Aldehydes and Ketones—An Astonishingly Simple Access to Optically Active α‐Hydrazino Carbonyl Compounds. AngewandteChemie International Edition. 2003. 42(9): 975–978. https://doi.org/10.1002/anie.200390283.
Dalko P.I., Moisan L. In the golden age of organocatalysis. AngewandteChemie International Edition. 2004. 43(39): 5138–5175. https://doi.org/10.1002/anie.200400650.
Turner, A., Jaffrès, P.A., MacLean, E.J., Villemin, D., McKee, V., Hix, G.B. Hydrothermal synthesis and crystal structure of two Co phosphonates containing trifunctional phosphonate anions: Co3(O3PCH2NH2CH2PO3)2 and Co3(O3 PCH2-NC4H7-C2)2• 5H2O. Dalton Transactions. 2003. (7): 1314–1319.
https://doi.org/10.1039/B212266A.
Yang B.P., Mao J.G., Sun Y.Q., Zhao H.H., Clearfield A. Syntheses, characterizations, and crystal structures of three new metal phosphonocarboxylates with a layered and a microporous structure. European Journal of Inorganic Chemistry. 2003. 2003(23): 4211–4217. https://doi.org/10.1002/ejic.200300363.
Shi X., Zhu G., Qiu S., Huang K., Yu J., Xu R. Zn2[(S)-O3PCH2NHC4H7CO2]2: a homochiral 3D zinc phosphonate with helical channels. AngewandteChemie (International ed. in English). 2004. 43(47): 6482–6485.
https://doi.org/10.1002/anie.200460724.
Yue Q., Yang J., Li G.H., Li G.D., Chen J.S. Homochiral porous lanthanide phosphonates with 1D triple-strand helical chains: synthesis, photoluminescence, and adsorption properties. Inorganic chemistry. 2006. 45(11): 4431–4439.