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Research Article

Tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions

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Pages 10-19 | Received 27 Dec 2022, Accepted 02 Feb 2023, Published online: 24 Feb 2023

References

  • a) Lehn J.-M. Toward self-organization and complex matter. Science. 2002;295(5564):2400–2403. b) Philp, D.; Stoddart, J. F. Angew. Chem. Int. Ed. 1996, 35, 1155-1196; c) Amabilino, D. B.; Smith, D. K.; Steed. J. W. Chem. Soc. Rev. 2017, 46, 2404-2420; d) Antipin, I. S. et al. Russ. Chem. Rev. 2021, 90, 895-1107.
  • a) Kulkarni C., Meijer E. W., Palmans A. R. A. Cooperativity scale: a structure–mechanism correlation in the self-assembly of benzene-1,3,5-tricarboxamides. Acc. Chem. Res. 2017;50(8):1928–1936. b) Su, L.; Mosquera, J.; Mabesoone, M. F. J.; Schoenmakers, S. M. C.; Muller, C.; Vleugels, M. E. J.; Dhiman, S.; Wijker, S.; Palmans, A. R. A.; Meijer, E. W. Science. 2022, 377, 213-218; c) Schnitzer, T.; Preuss, M. D.; van Basten, J.; Schoenmakers, S. M. C.; Spiering, A. J. H.; Vantomme, G. and Meijer, E. W. Angew. Chem. Int. Ed. 2022, 61, e202206738; d) Schoenmakers, S. M. C.; Spiering, A. J. H.; Herziger, S.; Böttcher, C.; Haag, R.; Palmans, A. R. A. and Meijer, E. W. ACS Macro Letters. 2022, 11(5), 711-715.
  • a) Beseniusa P., Portaleb G., Bomansc P. H. H., et al. Controlling the growth and shape of chiral supramolecular polymers in water. PNAS. 2010;107(42):17888–17893. b) Kotova, O.; Daly, R.; dos Santos, C. M. G.; Boese, M.; Kruger, P. E.; Boland, J. J. and Gunnlaugsson, T. Angew. Chem. Int. Ed. 2012, 51, 7208-7212; c) Lynes, A. D.; Hawes, C. S.; Byrne, K.; Schmitt, W. and Gunnlaugsson, T. Dalton Trans. 2018, 47, 5259-5268; d) Lynes, A. D.; Hawes, C. S.; Ward, E. N.; Haffner, B.; Möbius, M. E.; Byrne, K.; Schmitt, W.; Pal, R. and Gunnlaugsson, T. Cryst. Eng. Comm. 2017, 19, 1427-1438; e) Kotova, O.; Bradberry, S. J.; Savyasachi, A. J. and Gunnlaugsson, T. Dalton Trans. 2018, 47, 16377-16387.
  • a) Eliseeva S. V., Bünzli J.-C. G. Rare earths: jewels for functional materials of the future. New J. Chem. 2011;35(6):1165–1176. b) Li, X.-Z.; Tian, C.-B.; Sun, Q.-F. Chem. Rev. 2022, 122(6),6374-6458; c) Heffern, M. C.; Matosziuk, L. M.; Meade, T. J. Chem. Rev. 2014, 114, 4496-4539; d) Bell, D. J.; Natrajan, L. S.; Riddell, I. A. Coord. Chem. Rev. 2022, 472, 214786.
  • a) Eliseeva S. V., Bünzli J.-C. G.Lanthanide luminescence for functional materials and bio-sciences. Chem. Soc. Rev. 2010;39(1):189–227. b) Binnemans, K. Coord. Chem. Rev. 2015, 295, 1-45.
  • a) Bradberry S. J., Savyasachi A. J., Martínez-Calvo M., et al. Development of responsive visibly and NIR luminescent and supramolecular coordination self-assemblies using lanthanide ion directed synthesis. Coord. Chem. Rev. 2014;273-274:225–241. b) Barry, D. E.; Caffrey, D. F.; Gunnlaugsson, T. Coord. Chem. Rev. 2016, 45, 3244-3274; c) Xian, T.; Meng, Q.; Gao, F.; Hu, M.; Wang, X. Coord. Chem. Rev. 2023, 474, 214866.
  • Chauvin A.-S., Gumy F., Imbert D., et al. Europium and terbium tris (dipicolinates) as secondary standards for quantum yield determination. Spectrosc. Lett. 2004;37(5):517–532. erratum: Chauvin, A.-S.; Gumy, F.; Imbert, D.; Bünzli, J.-C. G. Spectrosc. Lett. 2006, 40, 193.
  • a) Nozary H., Piguet C., Tissot P., et al. Bent tridentate receptors in calamitic mesophases with predetermined photophysical properties: new luminescent lanthanide-containing materials, J. Am. Chem. Soc. 1998;120: 12274–12288. b) Shavaleev, N. M.; Gumy, F.; Scopelliti, R. and Bünzli, J.-C. G. Inorg. Chem. 2009, 48, 5611-5613; c) Di Pietro, S.; Gautier, N.; Imbert, D.; Pécauta, J. and Mazzanti, M. Dalton Trans. 2016, 45, 3429-3442.
  • a) Leonard J. P., Jensen P., McCabe T., et al. Self-assembly of chiral luminescent lanthanide coordination bundles. J. Am. Chem. Soc. 2007;129(36):10986–10987. b) Kotova, O.; Kitchen, J. A.; Lincheneau, C.; Peacock, R. D. and Gunnlaugsson, T. Chem. Eur. J. 2013, 19, 16181-16186.
  • a) Starck M., MacKenzie L. E., Batsanov A. S., et al. Excitation modulation of Eu:BPEPC based complexes as low-energy reference standards for circularly polarised luminescence (CPL). Chem. Commun. 2019;55(94):14115–14118. b) Andres, J.; Chauvin, A.-S. Eur. J. Inorg. Chem. 2010, 2700-2713; c) Caffrey, D.; Gunnlaugsson, T. Dalton Trans. 2014, 43, 17964-17970; c) Johnson, K. R.; de Bettencourt-Dias, A. Inorg. Chim Acta. 2021, 514, 120003; d) Monteiro, J. H. S. K.; Fetto, N. R.; Tucker, M. J.; Sigoli, F. A.; de Bettencourt-Dias, A. J. Lumin. 2022, 245, 118768; e) Rajah, D.; Pfrunder, M. C.; Chong, B. S. K.; Ireland, A. R.; Etchells, I. M. and Moore, E. G. Dalton Trans. 2021, 50, 7400-7408; f) Kotova, O.; O’Reilly, C.; Barwich, S. T.; Mackenzie, L. E.; Lynes, A. D.; Savyasachi, A. J.; Ruether, M.; Pal, R.; Möbius, M.; Gunnlaugsson, T. Chem. 2022, 8(5), 1395-1414.
  • D’Aléo A., Picot A., Beeby A., et al. Efficient sensitization of europium, ytterbium, and neodymium functionalized tris-dipicolinate lanthanide complexes through tunable charge-transfer excited states. Inorg. Chem. 2008;47(22):10258–10268.
  • a) Picot A., D’Aléo A., Baldeck P. L., et al. Long-lived two-photon excited luminescence of water-soluble europium complex:  applications in biological imaging using two-photon scanning microscopy. J. Am. Chem. Soc. 2008;130(5):1532–1533. b) D’Aléo, A.; Pointillart, F.; Ouahabb, L.; Andraudc, C.; Maury, O. Coord. Chem. Rev. 2012, 256, 1604-1620.
  • a) Barsu C., Fortrie R., Nowika K., et al., Synthesis of chromophores combining second harmonic generation and two photon induced fluorescence properties. Chem. Commun. 2006;45:4744–4746. b) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922.
  • a) Gampp H., Maeder M., Meyer C. J., et al. Calculation of equilibrium constants from multiwavelength spectroscopic data—IV model-free least-squares refinement by use of evolving factor analysis. Talanta. 1986;33(12):943–951. b) Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbìhler, A. D. Talanta 1985, 32, 1133-1139.
  • Picot A., Feuvrie C., Barsu C., et al. Synthesis, structures, optical properties, and TD-DFT studies of donor-π-conjugated dipicolinic acid/ester/amide ligands. Tetrahedron. 2008;64(2):399–411.
  • Abergel R. J., Kozimor S. A. Innovative f-element chelating strategies. Inorg. Chem. 2020;59(1):4–7.
  • Lakowicz J. R. Principles of fluorescent spectroscopy. 3rd ed. New York NY: Springer; 2006. p. 954.
  • a) Gampp H., Maeder M., Meyer C. J., et al. Calculation of equilibrium constants from multiwavelength spectroscopic data—IV model-free least-squares refinement by use of evolving factor analysis. Talanta. 1986;33(12):943–951. b) Gampp, H., Maeder, M., Meyer, C. J., Zuberbìhler, A. D., Talanta 1985, 32, 1133-1139.
  • Bruker-AXS. Bruker APEX-3, Bruker-AXS Inc. Madison, WI; 2016.
  • Bruker-AXS. SADABS 2016/2, Bruker-AXS Inc. Madison, WI; 2016.
  • Sheldrick G. M. SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. Sect. A. 2015;71(1):3–8.
  • Sheldrick G. M. Crystal structure refinement with SHELXL. Acta Crystallogr., Sect. C: Struct. Chem. 2015;71(1):3–8
  • Dolomanov O. V., Bourhis L. J., Gildea R. J., et al. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009;42(2):339–341.