{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T02:49:49Z","timestamp":1785898189238,"version":"3.56.0"},"reference-count":117,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2021,2,24]],"date-time":"2021-02-24T00:00:00Z","timestamp":1614124800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure\u2013property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.<\/jats:p>","DOI":"10.3390\/molecules26051214","type":"journal-article","created":{"date-parts":[[2021,2,25]],"date-time":"2021-02-25T02:36:13Z","timestamp":1614220573000},"page":"1214","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["1,3-Diketone Calix[4]arene Derivatives\u2014A New Type of Versatile Ligands for Metal Complexes and Nanoparticles"],"prefix":"10.3390","volume":"26","author":[{"given":"Sergey N.","family":"Podyachev","sequence":"first","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1699-6741","authenticated-orcid":false,"given":"Rustem R.","family":"Zairov","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Asiya R.","family":"Mustafina","sequence":"additional","affiliation":[{"name":"Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,24]]},"reference":[{"key":"ref_1","unstructured":"Steed, J.W., Turner, D.R., and Wallace, K.J. (2007). Core Concepts in Supramolecular Chemistry and Nanochemistry, John Wiley."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Gleiter, R., and Hopf, H. (2004). Modern Cyclophane Chemistry, Wiley-VCH.","DOI":"10.1002\/3527603964"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1002\/anie.199507131","article-title":"Calixarenes, macrocycles with (almost) unlimited possibilities","volume":"34","year":"1995","journal-title":"Angew. Chemie Int. Ed. Engl."},{"key":"ref_4","unstructured":"Gutsche, C.D. (2008). Calixarenes: An introduction, Royal Society of Chemistry. [2nd ed.]. Monographs in Supramolecular Chemistry."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Vicens, J., Harrowfield, J., and Baklouti, L. (2007). Calixarenes in the Nanoworld, Springer.","DOI":"10.1007\/978-1-4020-5022-4"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Neri, P., Sessler, J.L., and Wang, M.X. (2016). Calixarenes and Beyond, Springer.","DOI":"10.1007\/978-3-319-31867-7"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"9657","DOI":"10.1021\/acs.chemrev.8b00605","article-title":"Revisiting fluorescent calixarenes: From molecular sensors to smart materials","volume":"119","author":"Kumar","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"8333","DOI":"10.1002\/chem.201605246","article-title":"Design of organic macrocycle-modified iron oxide nanoparticles for drug delivery","volume":"23","author":"Skorjanc","year":"2017","journal-title":"Chem. A Eur. J."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"824","DOI":"10.1080\/03067319.2019.1616708","article-title":"Sensitive detection of heavy metals ions based on the calixarene derivatives-modified piezoelectric resonators: A review","volume":"99","author":"Eddaif","year":"2019","journal-title":"Int. J. Environ. Anal. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1038\/s41428-018-0126-7","article-title":"Designer supramolecular polymers with specific molecular recognitions","volume":"51","author":"Haino","year":"2019","journal-title":"Polym. J."},{"key":"ref_11","first-page":"1","article-title":"Calix-based nanoparticles: A review","volume":"374","author":"Kongor","year":"2016","journal-title":"Top. Curr. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Asfari, M.-Z., B\u00f6hmer, J., Harrowfield, J., and Vicens, J. (2002). Calixarenes 2001, Kluwer Academic Publishers.","DOI":"10.1007\/0-306-47522-7"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"710","DOI":"10.1002\/ajoc.201500178","article-title":"Rational strategies for the selective functionalization of calixarenes","volume":"4","author":"Lavendomme","year":"2015","journal-title":"Asian J. Org. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"134","DOI":"10.6060\/mhc170512a","article-title":"Thiacalix[4]arene\u2019s lower rim derivatives: Synthesis and supramolecular properties","volume":"10","author":"Solovieva","year":"2017","journal-title":"Macroheterocycles"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2545","DOI":"10.1080\/00397911.2020.1766080","article-title":"Recent advances in upper rim functionalization of resorcin[4]arene derivatives: Synthesis and applications","volume":"50","author":"Gajjar","year":"2020","journal-title":"Synth. Commun."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Gloe, K. (2005). Macrocyclic Chemistry: Current Trends and Future Perspectives, Springer.","DOI":"10.1007\/1-4020-3687-6"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Gloe, K. (2005). Ligand design for base metal recovery. Macrocyclic Chemistry\u2014Current Trends and Future Perspectives, Springer.","DOI":"10.1007\/1-4020-3687-6"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2394","DOI":"10.1080\/01496395.2016.1209219","article-title":"Calixarene-based extractants for heavy metal ions removal from aqueous solutions","volume":"51","author":"Konczyk","year":"2016","journal-title":"Sep. Sci. Technol."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Staniszewski, B., and Urbaniak, W. (2009). A simple and efficient synthesis of 3-substituted derivatives of pentane-2,4-dione. Chem. Pap., 63.","DOI":"10.2478\/s11696-008-0097-9"},{"key":"ref_20","first-page":"1855","article-title":"Recent advances in the chemistry of 1,3-diketones: Structural modifications and synthetic applications","volume":"7","author":"Maioli","year":"2005","journal-title":"Curr. Org. Chem."},{"key":"ref_21","first-page":"1","article-title":"\u03b2-diketones: Important intermediates for drug synthesis","volume":"4","author":"Pradhan","year":"2015","journal-title":"Int. J. Pharm. Res. Allied Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1655","DOI":"10.1002\/ejic.201601314","article-title":"\u03b2-Diketones as scaffolds for anticancer drug design\u2014From organic building blocks to natural products and metallodrug components","volume":"2017","author":"Kljun","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/S0168-1273(05)35003-3","article-title":"Rare-earth beta-diketonates","volume":"35","author":"Binnemans","year":"2005","journal-title":"Handb. Phys. Chem. Rare Earths"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1099","DOI":"10.1016\/j.ccr.2008.07.013","article-title":"The evolution of \u03b2-diketone or \u03b2-diketophenol ligands and related complexes","volume":"253","author":"Vigato","year":"2009","journal-title":"Coord. Chem. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.ccr.2017.11.007","article-title":"Recent developments in the metallo-supramolecular chemistry of oligo-\u03b2-diketonato ligands","volume":"375","author":"Brock","year":"2018","journal-title":"Coord. Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"8209","DOI":"10.1021\/ic048992n","article-title":"Porous Cu\u2212Cd mixed-metal\u2212organic frameworks constructed from Cu(Pyac) 2 (bis[3-(4-pyridyl)pentane-2,4-dionato]copper(II))","volume":"43","author":"Chen","year":"2004","journal-title":"Inorg. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1002\/anie.200905497","article-title":"Hierarchical self-assembly of a chiral metal-organic framework displaying pronounced porosity","volume":"49","author":"Clegg","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4283","DOI":"10.1021\/cr8003983","article-title":"Lanthanide-based luminescent hybrid materials","volume":"109","author":"Binnemans","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/S0010-8545(99)00054-5","article-title":"Spectroscopic properties and design of highly luminescent lanthanide coordination complexes","volume":"196","author":"Malta","year":"2000","journal-title":"Coord. Chem. Rev."},{"key":"ref_30","first-page":"11","article-title":"Supramolecularly Organized Lanthanide Complexes for Efficient Metal Excitation and Luminescence as Sensors in Organic and Biological Applications","volume":"1","author":"Brunet","year":"2012","journal-title":"Curr. Chem. Biol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1048","DOI":"10.1039\/b406082m","article-title":"Taking advantage of luminescent lanthanide ions","volume":"34","author":"Piguet","year":"2005","journal-title":"Chem. Soc. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/j.jlumin.2019.05.035","article-title":"Novel tetrakis lanthanide \u03b2-diketonate complexes: Structural study, luminescence properties and temperature sensing","volume":"213","author":"Mara","year":"2019","journal-title":"J. Lumin."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"921","DOI":"10.1016\/j.chembiol.2020.07.009","article-title":"Lanthanide-based optical probes of biological systems","volume":"27","author":"Cho","year":"2020","journal-title":"Cell Chem. Biol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"213405","DOI":"10.1016\/j.ccr.2020.213405","article-title":"Lanthanide spectroscopy in probing structure-property correlation in multi-site photoluminescent phosphors","volume":"420","author":"Gupta","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1007\/s10895-005-2826-6","article-title":"Progress in lanthanides as luminescent probes","volume":"15","author":"Laitala","year":"2005","journal-title":"J. Fluoresc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1676","DOI":"10.1021\/ac00285a037","article-title":"Time-resolved fluorometric determination of terbium in aqueous solution","volume":"57","author":"Hemmila","year":"1985","journal-title":"Anal. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"4496","DOI":"10.1021\/cr400477t","article-title":"Lanthanide probes for bioresponsive imaging","volume":"114","author":"Heffern","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"117174","DOI":"10.1016\/j.jlumin.2020.117174","article-title":"Lanthanide-sensitized luminescence and chemiluminescence in the systems containing most often used medicines; a review","volume":"222","author":"Kaczmarek","year":"2020","journal-title":"J. Lumin."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"286","DOI":"10.1134\/S1061934820030144","article-title":"Increasing Sensitivity of the Luminescence Determination of Lanthanides Using Their Complexes","volume":"75","author":"Meshkova","year":"2020","journal-title":"J. Anal. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5291","DOI":"10.1021\/jp7119763","article-title":"Pressure-induced phase transitions on a liquid crystalline europium(III) Complex","volume":"112","author":"Yang","year":"2008","journal-title":"J. Phys. Chem. B"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1002\/cphc.200700658","article-title":"Listening to Lanthanide Complexes: Determination of the Intrinsic Luminescence Quantum Yield by Nonradiative Relaxation","volume":"9","author":"Yang","year":"2008","journal-title":"ChemPhysChem"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1016\/S0040-4039(00)76659-7","article-title":"Synthesis of and amine recognition with a Cu(II)-bridged biscalix[4]arene","volume":"35","author":"Fujimoto","year":"1994","journal-title":"Tetrahedron Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9077","DOI":"10.1016\/j.tetlet.2006.10.082","article-title":"Mo(CO)6-mediated synthesis of calix[4]arenes carrying \u03b2-hydroxy ketones or \u03b1,\u03b2-unsaturated-\u03b2-amino ketones","volume":"47","author":"Senthilvelan","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3664","DOI":"10.1021\/jo200580m","article-title":"Calix[4]arenes with two different chemical modifications at the bridges","volume":"76","author":"Kuno","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"7172","DOI":"10.1021\/jo901450x","article-title":"Incorporation of substituents at the methylene linkages of the calix[5]arene skeleton","volume":"74","author":"Kogan","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"7327","DOI":"10.1021\/jo801187z","article-title":"Functionalization of the methylene bridges of the calix[6]arene scaffold","volume":"73","author":"Kogan","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Itzhak, N., Kogan, K., and Biali, S.E. (2011). Preparation of calix[8]arene derivatives functionalized at a single methylene bridge. Eur. J. Org. Chem., 6581\u20136585.","DOI":"10.1002\/ejoc.201100779"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.1055\/s-0033-1341058","article-title":"Design and synthesis of a new kind of cavitand: Tetrapyrazolylcalix[4] arenes and their supramolecular assemblies","volume":"25","author":"Jiang","year":"2014","journal-title":"Synlett"},{"key":"ref_49","first-page":"1117","article-title":"Synthesis, crystal structure and anti-integrase activity of 25,27-bis[(Z)-4-(p-methoxyphenyl)-4-hydroxybut-3-en-2-one-1-methyl]-26,28-dihydroxycalix[4]arene","volume":"33","author":"Luo","year":"2014","journal-title":"Chin. J. Struct. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1016\/j.cclet.2014.03.012","article-title":"Synthesis and anti-integrase evaluation of novel calix[4]arene derivatives containing the triazolyl 1,3-diketo moiety","volume":"25","author":"Luo","year":"2014","journal-title":"Chin. Chem. Lett."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1002\/ardp.201400390","article-title":"Synthesis, biological evaluation and molecular docking of calix[4]arene-based \u03b2-diketo derivatives as HIV-1 integrase inhibitors","volume":"348","author":"Luo","year":"2015","journal-title":"Arch. Pharm."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2000","DOI":"10.1007\/s11172-006-0542-2","article-title":"Synthesis of tris(\u03b2-diketones) and study of their complexation with some transition metals","volume":"55","author":"Podyachev","year":"2006","journal-title":"Russ. Chem. Bull."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4130","DOI":"10.1039\/C4NJ00637B","article-title":"A facile synthetic route to convert Tb(III) complexes of novel tetra-1,3-diketone calix[4]resorcinarene into hydrophilic luminescent colloids","volume":"38","author":"Shamsutdinova","year":"2014","journal-title":"New J. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2447","DOI":"10.1016\/j.tet.2016.03.068","article-title":"Structure impact in antenna effect of novel upper rim substituted tetra-1,3-diketone calix[4]arenes on Tb(III) green and Yb(III) NIR-luminescence","volume":"72","author":"Zairov","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1526","DOI":"10.1039\/C6NJ03381D","article-title":"Synthesis, metal binding and spectral properties of novel bis-1,3-diketone calix[4]arenes","volume":"41","author":"Podyachev","year":"2017","journal-title":"New J. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"6153","DOI":"10.1021\/ja00226a034","article-title":"Calixarenes. 22. Synthesis, properties, and metal complexation of aminocalixarenes","volume":"110","author":"Gutsche","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1016\/S0040-4020(01)80077-6","article-title":"Chloromethylation of calixarenes and synthesis of new water soluble macrocyclic hosts","volume":"45","author":"Almi","year":"1989","journal-title":"Tetrahedron"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2695","DOI":"10.1016\/j.tetlet.2018.05.084","article-title":"The enhancement of luminescent properties of Tb3+ complexes with tetra-1,3-diketone ligands promoted by the tetrathiacalix[4]arene scaffold","volume":"59","author":"Podyachev","year":"2018","journal-title":"Tetrahedron Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"5397","DOI":"10.1016\/j.tet.2017.07.043","article-title":"Influence of upper rim dibromo-substitution in bis-1,3-diketone calix[4]arenes on spectral properties of ligands and their lanthanide complexes","volume":"73","author":"Podyachev","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"8298","DOI":"10.1039\/D0DT00709A","article-title":"A simple synthetic approach to enhance the thermal luminescence sensitivity of Tb3+ complexes with thiacalix[4]arene derivatives through upper-rim bromination","volume":"49","author":"Podyachev","year":"2020","journal-title":"Dalton Trans."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1007\/s00604-018-2923-2","article-title":"Polystyrenesulfonate-coated nanoparticles with low cytotoxicity for determination of copper(II) via the luminescence of Tb(III) complexes with new calix[4]arene derivatives","volume":"185","author":"Zairov","year":"2018","journal-title":"Microchim. Acta"},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Emsley, J. (1984). The composition, structure and hydrogen bonding of the \u03b2-diketones. Complex Chemistry, Springer.","DOI":"10.1002\/chin.198518359"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"13948","DOI":"10.1021\/jp064286r","article-title":"Computational study on the bond dissociation enthalpies in the enolic and ketonic forms of \u03b2-diketones: Their influence on metal\u2212ligand bond enthalpies","volume":"110","author":"Gomes","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2750","DOI":"10.1021\/jp031243r","article-title":"Reaction paths of keto\u2212enol tautomerization of \u03b2-diketones","volume":"108","author":"Yamabe","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"8198","DOI":"10.1021\/jo801183y","article-title":"First kinetic discrimination between carbon and oxygen reactivity of enols","volume":"73","author":"Mejuto","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2266","DOI":"10.1021\/ja031927c","article-title":"Direct determination of hydrogen-bonded structures in resonant and tautomeric reactions using ultrafast electron diffraction","volume":"126","author":"Srinivasan","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Hansen, P.E., and Spanget-Larsen, J. (2017). NMR and IR investigations of strong intramolecular hydrogen bonds. Molecules, 22.","DOI":"10.3390\/molecules22040552"},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Le, Q.T.H., Umetani, S., Suzuki, M., and Matsui, M. (1997). \u03b1-Substituted \u03b2-diketones: Effect of the \u03b1 substituent on the complexation and selectivity for lanthanides. J. Chem. Soc. Dalton Trans., 643\u2013648.","DOI":"10.1039\/a607287i"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"3930","DOI":"10.1039\/C9DT00286C","article-title":"Structural and photophysical properties of Tb3+-tetra-1,3-diketonate complexes controlled by calix[4]arene-tetrathiacalix[4]arene scaffolds","volume":"48","author":"Podyachev","year":"2019","journal-title":"Dalton Trans."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1958","DOI":"10.1134\/S1070363217090110","article-title":"Synthesis of 1,3-diketo derivatives of calix[4]arene with nonyl substituents at the lower rim as novel efficient sensibilizers of Tb3+ luminescence","volume":"87","author":"Podyachev","year":"2017","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","unstructured":"Massi, M., and Odgen, M.I. (2017). Luminescent lanthanoid calixarene complexes and materials. Materials, 10.","DOI":"10.3390\/ma10121369"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1023\/A:1014406709512","article-title":"Can thiacalixarene surpass calixarene?","volume":"41","author":"Iki","year":"2001","journal-title":"J. Incl. Phenom."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Iki, N., Horiuchi, T., Oka, H., Koyama, K., Morohashi, N., Kabuto, C., and Miyano, S. (2001). Energy transfer luminescence of Tb3+ ion complexed with calix[4]arenetetrasulfonate and the thia and sulfonyl analogue. The effect of bridging groups. J. Chem. Soc. Perkin Trans. 2, 2219\u20132225.","DOI":"10.1039\/b009151k"},{"key":"ref_74","first-page":"19","article-title":"On the design of highly luminescent lanthanide complexes","volume":"293\u2013294","year":"2015","journal-title":"Coord. Chem. Rev."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"213098","DOI":"10.1016\/j.ccr.2019.213098","article-title":"A structural and spectroscopic overview of molecular lanthanide complexes with fluorinated O-donor ligands","volume":"404","author":"Hyre","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"9475","DOI":"10.1039\/C8TC01288A","article-title":"A photostable vitrified film based on a terbium(III) \u03b2-diketonate complex as a sensing element for reusable luminescent thermometers","volume":"6","author":"Lapaev","year":"2018","journal-title":"J. Mater. Chem. C"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1039\/c0nj01010c","article-title":"Lanthanide-based luminescent molecular thermometers","volume":"35","author":"Brites","year":"2011","journal-title":"New J. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"7494","DOI":"10.1039\/C9TC00607A","article-title":"Thermo-sensitive luminescence of lanthanide complexes, clusters, coordination polymers and metal\u2013organic frameworks with organic photosensitizers","volume":"7","author":"Hasegawa","year":"2019","journal-title":"J. Mater. Chem. C"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/adom.201801239","article-title":"Lanthanide-based thermometers: At the cutting-edge of luminescence thermometry","volume":"7","author":"Brites","year":"2019","journal-title":"Adv. Opt. Mater."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"3357","DOI":"10.1002\/cphc.201200367","article-title":"Complex formation of d-metal ions at the interface of TbIII -doped silica nanoparticles as a Basis of substrate-responsive TbIII-centered luminescence","volume":"13","author":"Davydov","year":"2012","journal-title":"ChemPhysChem"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1018","DOI":"10.1007\/s11051-012-1018-y","article-title":"The effect of the core morphology of Eu(III)-doped nanoparticles on the ion exchange versus energy transfer between Eu(III) in the core and Cu(II) ions at the interface","volume":"14","author":"Zairov","year":"2012","journal-title":"J. Nanopart. Res."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"6273","DOI":"10.1039\/D0TC00625D","article-title":"A vitrified film of an anisometric europium(iii) \u03b2-diketonate complex with a low melting point as a reusable luminescent temperature probe with excellent sensitivity in the range of 270\u2013370 K","volume":"8","author":"Lapaev","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1016\/j.colsurfb.2016.04.055","article-title":"Polystyrene latex particles containing europium complexes prepared by miniemulsion polymerization using bovine serum albumin as a surfactant for biochemical diagnosis","volume":"145","author":"Aikawa","year":"2016","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"2643","DOI":"10.1021\/ac048360i","article-title":"Synthesis, characterization, and application of Eu(III), Tb(III), Sm(III), and Dy(III) lanthanide chelate nanoparticle labels","volume":"77","author":"Huhtinen","year":"2005","journal-title":"Anal. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"Chandra, A., Prasad, S., Gigli, G., and del Mercato, L.L. (2020). Fluorescent Nanoparticles for Sensing, Elsevier Ltd.. [1st ed.].","DOI":"10.1016\/B978-0-08-102828-5.00006-1"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.jphotochemrev.2019.03.001","article-title":"Fluorescent pH nanosensors: Design strategies and applications","volume":"39","author":"Shamsipur","year":"2019","journal-title":"J. Photochem. Photobiol. C Photochem. Rev."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"3146","DOI":"10.1021\/la8032572","article-title":"Novel highly charged silica-coated Tb(III) nanoparticles with fluorescent properties sensitive to ion exchange and energy transfer processes in aqueous dispersions","volume":"25","author":"Mustafina","year":"2009","journal-title":"Langmuir"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"42016","DOI":"10.1021\/acsami.0c13690","article-title":"Tailoring the Design of a Lanthanide Complex\/Magnetic Ferrite Nanocomposite for Efficient Photoluminescence and Magnetic Hyperthermia Performance","volume":"12","author":"Das","year":"2020","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"960","DOI":"10.1021\/ac061477h","article-title":"Sensitized luminescent terbium nanoparticles: Preparation and time-resolved fluorescence assay for DNA","volume":"79","author":"Chen","year":"2007","journal-title":"Anal. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"304","DOI":"10.1002\/anie.200804231","article-title":"Europium-based fluorescence nanoparticle sensor for rapid and ultrasensitive detection of an anthrax biomarker","volume":"48","author":"Ai","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1016\/j.bios.2017.03.027","article-title":"Dual lanthanide-doped complexes: The development of a time-resolved ratiometric fluorescent probe for anthrax biomarker and a paper-based visual sensor","volume":"94","author":"Wang","year":"2017","journal-title":"Biosens. Bioelectron."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"5830","DOI":"10.1016\/j.biomaterials.2014.03.080","article-title":"Visible-light-excited and europium-emissive nanoparticles for highly-luminescent bioimaging invivo","volume":"35","author":"Wu","year":"2014","journal-title":"Biomaterials"},{"key":"ref_93","doi-asserted-by":"crossref","unstructured":"Santos, J.A.O., Mutti, A.M.G., Bispo-Jr, A.G., Pires, A.M., and Lima, S.A.M. (2020). Red-emitting hybrid based on Eu3+-dbm complex anchored on silica nanoparticles surface by carboxylic acid for biomarker application. Materials, 13.","DOI":"10.3390\/ma13235494"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1039\/C6SC02243J","article-title":"Dual-emissive nanoarchitecture of lanthanide-complex-modified silica particles for in vivo ratiometric time-gated luminescence imaging of hypochlorous acid","volume":"8","author":"Ma","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"15021","DOI":"10.1039\/D0NR03373A","article-title":"Luminescent lanthanide metal-organic framework nanoprobes: From fundamentals to bioapplications","volume":"12","author":"Li","year":"2020","journal-title":"Nanoscale"},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1016\/j.jallcom.2008.09.201","article-title":"Synthesis and characterization of nano-scale Terbium (III)-trimesic acid (TMA)-1,10-phenanthroline(phen) luminescent complex","volume":"477","author":"Zheng","year":"2009","journal-title":"J. Alloys Compd."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"2151","DOI":"10.1021\/ja8058843","article-title":"Nanoparticles of Adaptive Supramolecular Networks Self-Assembled from Nucleotides and Lanthanide Ions","volume":"131","author":"Nishiyabu","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"1224","DOI":"10.1557\/mrc.2018.107","article-title":"Europium(III)-induced water-soluble nano-aggregates of hyaluronic acid and chitosan: Structure and fluorescence","volume":"8","author":"Guo","year":"2018","journal-title":"MRS Commun."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1016\/j.surfcoat.2014.11.076","article-title":"Impact of polyelectrolyte coating in fluorescent response of Eu(III)-containing nanoparticles on small chelating anions including nucleotides","volume":"271","author":"Zairov","year":"2015","journal-title":"Surf. Coat. Technol."},{"key":"ref_100","doi-asserted-by":"crossref","unstructured":"Davydov, N., Zairov, R., Mustafina, A., Syakayev, V., Tatarinov, D., Mironov, V., Eremin, S., Konovalov, A., and Mustafin, M. (2013). Determination of fluoroquinolone antibiotics through the fluorescent response of Eu(III) based nanoparticles fabricated by layer-by-layer technique. Anal. Chim. Acta, 784.","DOI":"10.1016\/j.aca.2013.04.054"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1016\/j.colsurfb.2011.07.039","article-title":"Synthesis and photophysical properties of colloids fabricated by the layer-by-layer polyelectrolyte assembly onto Eu(III) complex as a core","volume":"88","author":"Mustafina","year":"2011","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1134\/S1070428014040186","article-title":"Polymethoxyphenyl-substituted [2-(5-chloro-2-hydroxy-4-methylphenyl)-2-phenylvinyl]phosphine oxides: Synthesis and complexation with Eu(TTA)3","volume":"50","author":"Zairov","year":"2014","journal-title":"Russ. J. Org. Chem."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1016\/j.jcis.2017.08.038","article-title":"Surface modification of upconverting nanoparticles by layer-by-layer assembled polyelectrolytes and metal ions","volume":"508","author":"Palo","year":"2017","journal-title":"J. Colloid Interface Sci."},{"key":"ref_104","doi-asserted-by":"crossref","unstructured":"Zhang, R.J., Cui, J.W., Lu, D.M., and Hou, W.G. (2007). Study on high-efficiency fluorescent microcapsules doped with europium \u03b2-diketone complex by LbL self-assembly. Chem. Commun., 1547\u20131549.","DOI":"10.1039\/B701181D"},{"key":"ref_105","first-page":"895","article-title":"The effect of temperature and solvent on the morphology of microcapsules doped with a europium \u03b2-diketonate complex","volume":"3","author":"Cui","year":"2007","journal-title":"J. Chem. Soc. Dalton Trans."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"110057","DOI":"10.1016\/j.msec.2019.110057","article-title":"Dual red-NIR luminescent Eu Yb heterolanthanide nanoparticles as promising basis for cellular imaging and sensing","volume":"105","author":"Zairov","year":"2019","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_107","doi-asserted-by":"crossref","unstructured":"Zairov, R.R., Solovieva, A.O., Shamsutdinova, N.A., Podyachev, S.N., Shestopalov, M.A., Pozmogova, T.N., Miroshnichenko, S.M., Mustafina, A.R., and Karasik, A.A. (2019). Polyelectrolyte-coated ultra-small nanoparticles with Tb(III)-centered luminescence as cell labels with unusual charge effect on their cell internalization. Mater. Sci. Eng. C, 95.","DOI":"10.1016\/j.msec.2018.10.084"},{"key":"ref_108","doi-asserted-by":"crossref","unstructured":"Zairov, R., Mustafina, A., Shamsutdinova, N., Nizameev, I., Moreira, B., Sudakova, S., Podyachev, S., Fattakhova, A., Safina, G., and Lundstrom, I. (2017). High performance magneto-fluorescent nanoparticles assembled from terbium and gadolinium 1,3-diketones. Sci. Rep., 7.","DOI":"10.1038\/srep40486"},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1016\/j.colsurfa.2015.05.013","article-title":"Interfacial interactions of hard polyelectrolyte-stabilized luminescent colloids with substrates","volume":"482","author":"Shamsutdinova","year":"2015","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"1377","DOI":"10.1002\/slct.201600223","article-title":"Polyelectrolyte-stabilized nanotemplates based on Gd(III) complexes with macrocyclic tetra-1,3-diketones as a positive MR contrast agents","volume":"1","author":"Shamsutdinova","year":"2016","journal-title":"ChemistrySelect"},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"4320","DOI":"10.1021\/acs.jpcc.0c00312","article-title":"Paramagnetic Relaxation Enhancement in Hydrophilic Colloids Based on Gd(III) Complexes with Tetrathia- and Calix[4]arenes","volume":"124","author":"Zairov","year":"2020","journal-title":"J. Phys. Chem. C"},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-020-77512-1","article-title":"Terbium(III)-thiacalix[4]arene nanosensor for highly sensitive intracellular monitoring of temperature changes within the 303\u2013313 K range","volume":"10","author":"Zairov","year":"2020","journal-title":"Sci. Rep."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1016\/j.colsurfb.2017.10.070","article-title":"Tuning magnetic relaxation properties of \u201chard cores\u201d in core-shell colloids by modification of \u201csoft shell\u201d","volume":"162","author":"Shamsutdinova","year":"2018","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_114","doi-asserted-by":"crossref","unstructured":"Zairov, R., Khakimullina, G., Podyachev, S., Nizameev, I., Safiullin, G., Amirov, R., Vomiero, A., and Mustafina, A. (2017). Hydration number: Crucial role in nuclear magnetic relaxivity of Gd(III) chelate-based nanoparticles. Sci. Rep., 7.","DOI":"10.1038\/s41598-017-14409-6"},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"1325","DOI":"10.1007\/s11172-016-1456-2","article-title":"Nanoparticles based on gadolinium(III) and europium(III) complexes for biovisualization","volume":"65","author":"Zairov","year":"2016","journal-title":"Russ. Chem. Bull."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1002\/cmmi.267","article-title":"Influence of molecular parameters and increasing magnetic field strength on relaxivity of gadolinium- and manganese-based T1 contrast agents","volume":"4","author":"Caravan","year":"2009","journal-title":"Contrast Media Mol. Imaging"},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1016\/j.molliq.2018.07.075","article-title":"Tb(III) complexes with nonyl-substituted calix[4]arenes as building blocks of hydrophilic luminescent mixed polydiacetylene-based aggregates","volume":"268","author":"Elistratova","year":"2018","journal-title":"J. Mol. Liq."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/5\/1214\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:28:01Z","timestamp":1760160481000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/5\/1214"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2,24]]},"references-count":117,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2021,3]]}},"alternative-id":["molecules26051214"],"URL":"https:\/\/doi.org\/10.3390\/molecules26051214","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,2,24]]}}}