On the use of mixed thia/aza macrocycles in the development of fluorescent chemosensors for toxic heavy metals and fluorescent materials

References

• Sigel, A.; Sigel, H.; Sigel, R. K. O. Neurodegenerative Diseases and Metal Ions; New York: Wiley, 2006.
   Google Scholar
• Bordberg, G. F.; Fowler, B. A.; Nordberg, M.; Friberg, L. Handbook on the Toxicology of Metals, 3rd ed.; Amsterdam: Elsevier, 2007.
   Google Scholar
• de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515–1666. DOI: 10.1021/cr960386p.
   PubMed Web of Science ®Google Scholar
• Fabbrizzi, L. (Guest Ed.) Coord. Chem. Rev 2000, 205, 1. (Special Issue on Luminescent Sensors)
   Web of Science ®Google Scholar
• Rurack, K. Flipping the Light Switch “on”-the Design of Sensors Molecules That Show Cation-Induced Fluorescence Enhancement with Heavy and Transition Metal Ions. Spectrochim. Acta A 2001, 57, 2161–2195. DOI: 10.1016/S1386-1425(01)00492-9.
   PubMed Web of Science ®Google Scholar
• de Silva, A. P.; de Silva, S. A. Fluorescent Signaling Crown Ethers; “Switching on” of Fluorescence by Alkali Metal Ion Recognition and Binding in Situ. J. Chem. Soc. Chem. Commun. 1986, 23, 1709–1710. DOI: 10.1039/C39860001709.
   Google Scholar
• Bencini, A.; Lippolis, V. Probing Biologically and Environmentally Important Metal Ions with Fluorescent Chemosensors: Thermodynamic versus Optical Response Selectivity in Some Study Cases. Coord. Chem. Rev. 2012, 256, 149–169. DOI: 10.1016/j.ccr.2011.05.015.
   Web of Science ®Google Scholar
• Blake, A. J.; Bencini, A.; Caltagirone, C.; De Filippo, G.; Dolci, L. S.; Garau, A.; Isaia, F.; Lippolis, V.; Mariani, P.; Prodi, L.; et al. A New Pyridine-Based 12-Membered Macrocycle Functionalized with Different Fluorescent Subunits; Coordination Chemistry towards Cu2+, Zn2+, Cd2+, Hg2+, and Pb2+. Dalton Trans. 2004, 2771–2779. DOI: 10.1039/B407037B.
   PubMed Web of Science ®Google Scholar
• Aragoni, M. C.; Arca, M.; Bencini, A.; Blake, A. J.; Caltagirone, C.; De Filippo, G.; Devillanova, F. A.; Garau, A.; Gelbrich, T.; Hursthouse, M. B.; et al. Tuning the Selectivity/Specificity of Fluorescent Metal Ion Sensors Based on N2S2 Pyridine-Containing Macrocyclic Ligands by Changing the Fluorogenic Unit: Spectrofluorimetric and Metal Ion Binding Studies. Inorg. Chem. 2007, 46, 4548–4559. DOI: 10.1021/ic070169e.
   PubMed Web of Science ®Google Scholar
• Aragoni, M. C.; Arca, A.; Bencini, A.; Caltagirone, C.; Garau, A.; Isaia, A.; Light, M. E.; Lippolis, V.; Lodeiro, C.; Mameli, M.; et al. Zn2+/Cd2+ Optical Discrimination by Fluorescent Chemosensors Based on 8-Hydroxyquinoline Derivatives and Sulfur-Containing Macrocyclic Units. Dalton Trans. 2013, 42, 14516–14530. DOI: 10.1039/c3dt51292d.
   PubMed Web of Science ®Google Scholar
• Shamsipur, M.; Zahedi, M. M.; De Filippo, G.; Lippolis, V. Development of a Novel Flow Injection Liquid-Liquid Microextraction Method for the on-Line Sepration and Preconcentration for Determination of Zinc(II) Using 5-(8-Hydroxy-2-Quinolinylmethyl)2,8-Dithia-5-Aza-2,6-Pyridinophane as a Sensitive and Selective Fluorescent Sensors. Talanta. 2011, 85, 687–693. DOI: 10.1016/j.talanta.2011.04.049.
   PubMed Web of Science ®Google Scholar
• Mameli, M.; Aragoni, M. C.; Arca, M.; Caltagirone, C.; Demartin, F.; Farruggia, G.; De Filippo, G.; Devillanova, F. A.; Garau, A.; Isaia, F.; et al. A Selective. Nontoxic, off-on Fluorescent Molecular Sensor Based on 8-Hydroxyquinoline for Probing Cd2+ in Living Cells. Chem. Eur. J. 2010, 16, 919–930. DOI: 10.1002/chem.200902005.
   PubMed Web of Science ®Google Scholar
• Bazzicalupi, C.; Caltagirone, C.; Cao, Z.; Chen, Q.; Di Natale, C.; Garau, A.; Lippolis, V.; Lvova, L.; Liu, H.; Lundström, I.; et al. Multimodal Use of New Coumarin-Based Fluorescent Chemosensors: Towards Highly Selective Optical Sensors for Hg2+ Probing. Chem. Eur. J. 2013, 19, 14639–14653. DOI: 10.1002/chem.201302090.
   PubMed Web of Science ®Google Scholar
• Arca, M.; Caltagirone, C.; De Filippo, G.; Formica, M.; Fusi, V.; Giorgi, L.; Lippolis, V.; Prodi, L.; Rampazzo, E.; Scorciapino, M. A.; et al. A Fluorescent Ratiometric Nanosized System for the Determination of Pd II in Water. Chem. Commun 2014, 50, 15259–15262. DOI: 10.1039/C4CC07969H.
   PubMed Web of Science ®Google Scholar
• Shamsipur, M.; Hosseini, M.; Alizadeh, K.; Alizadeh, N.; Yari, A.; Caltagirone, C.; Lippolis, V. Novel Fluorimetric Bulk Optode Membrane Based on Dansylamidopropyl Pendant Arm Derivative of 1-Aza-4,10-Dithia-7-Oxacyclododecane ([12]aneNS2O) for Selective Subnanomolar Detection of Hg(II) Ions. Anal. Chim. Acta 2005, 533, 17–24. DOI: 10.1016/j.aca.2004.10.069.
   Web of Science ®Google Scholar
• Shamsipur, M.; Alizadeh, K.; Hosseini, M.; Caltagirone, C.; Lippolis, V. A Selective Optode Membrane for Silver Ion Based on Fluorescence Quenching of the Dansylamidopropyl Pendant Arm Derivative of 1-Aza-4,7,10-Trithiacyclododecane ([12]aneNS3). Sensors and Actuators B 2006, 113, 892–899. DOI: 10.1016/j.snb.2005.03.117.
   Web of Science ®Google Scholar
• Yam, V. W.-W.; Cheng, E. C.-C. Highlights on the Recent Advances in Gold Chemistry - a Photophysical Perspective. Chem. Soc. Rev. 2008, 37, 1806–1813. DOI: 10.1039/b708615f.
   PubMed Web of Science ®Google Scholar
• Fernández, E. J.; Laguna, A.; López-de-Luzuriaga, J. M.; Monge, M.; Montiel, M.; Olmos, M. E.; Pérez, J. Thallium(I) Acetylacetonate as Building Blocks of Luminescent Supramolecular Architectures. Organometallics 2004, 23, 774–782. DOI: 10.1021/om034167n.
   Web of Science ®Google Scholar
• (a) Uson, R.; Laguna, A.; Manzano, B. R.; Jones, P. G.; Sheldrick, G. M. Synthesis and reactivity of bimetallic Au–Ag polyfluorophenyl complexes; crystal and molecular structure of [{AuAg(C6F5)2(SC4H8)}n] and [{AuAg(C6F5)2(C6H6)}n] J. Chem. Soc., Dalton Trans. 1984, 2, 285–292. DOI: 10.1039/DT9840000285;.
   Google Scholar
  (b) Fernández, E. J.; Lopez de-Luzuriaga, J. M.; Olmos M. E. Vapochromism in Complexes of Stiochiometry [Au2Ag2R4L2]n. Zeitschrift fur Naturforsch. - Sect. B J. Chem. Sci. 2009, 64, 1500–1512. DOI: 0932–0776/09/1100–1500.
   Web of Science ®Google Scholar
• Blake, A. J.; Donamaria, R.; Lippolis, V.; López de Luzuriaga, J. M.; Manso, E.; Monge, M.; Olmos, M. E. Influence of Crown Thioether Ligands in the Structures and of Perhalophenyl Groups in the Optical Properties of Complexes with Argentoaurophilic Interactions. Inorg. Chem. 2014, 53, 10471–10484. DOI: 10.1021/ic501515c.
   PubMed Web of Science ®Google Scholar
• Donamaria, R.; Lippolis, V.; López de Luzuriaga, J. M.; Monge, M.; Nieddu, M.; Olmos, M. E. Influence of the Number of Metallophilic Interactions and Structures on the Optical Properties of Heterometallic Au/Ag Complexes with Mixed-Donor Macrocyclic Ligands. Inorg. Chem. 2018, 57, 11099–11112. DOI: 10.1021/acs.inorgchem.8b01687.
   PubMed Web of Science ®Google Scholar