New fluorescent chemosensors for heavy metal ions based on functionalized pendant arm derivatives of 7-anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane |
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Authors: | Aragoni M Carla Arca Massimiliano Bencini Andrea Blake Alexander J Caltagirone Claudia Danesi Andrea Devillanova Francesco A Garau Alessandra Gelbrich Thomas Isaia Francesco Lippolis Vito Hursthouse Michael B Valtancoli Barbara Wilson Claire |
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Institution: | Dipartimento di Chimica Inorganica ed Analitica, Università degli Studi di Cagliari, S.S. 554 Bivio per Sestu, 09042 Monserrato (CA), Italy. |
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Abstract: | Two new ligands 7-anthracenylmethyl-13-methylpyridyl-1,4,10-trioxa-7,13-diazacyclopentadecane (L4) and 7-anthracenylmethyl-13-(2,2-dimethyl-2-hydroxyethyl)-1,4,10-trioxa-7,13-diazacyclopentadecane (L(5)) have been synthesized and characterized. Both derive from 7-anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane (L(3)) and differ for having a differently functionalized pendant arm covalently attached to the remaining secondary nitrogen donor of the macrocyclic framework. The protonation and coordination behavior of L(4), L(5), and the unbranched L(3) with metal ions have been studied in MeCN/H2O (1:1 v/v, 298.1 K, I = 0.1 M) using potentiometric methods. The crystal structures of L(3), (H2L(3))(HL(3))](ClO4)3, and the complex CdL(3)(NO3)2] have been determined by single-crystal X-ray methods. The fluorescent behavior of L(3)-L(5) in the presence of Cu(II), Zn(II), Cd(II), Hg(II), and Pb(II) has been studied as a function of pH in MeCN/H2O (1:1 v/v). The presence of Cu(II), Hg(II), or Pb(II) does not affect the fluorescent behavior observed for the three free ligands upon changing the pH. Interestingly, the fluorescent emission of L(3) and L(5) is selectively enhanced only in the presence of Cd(II) at basic pH. The same effect is observed for L4 in the presence of Cd(II) or Zn(II) at about pH 7. |
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