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 (L5) have been synthesized and characterized. Both derive from 7-anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane (L3) 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 L4, L5, and the unbranched L3 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 L3, [(H2L3)(HL3)](ClO4)3, and the complex [CdL3(NO3)2] have been determined by single-crystal X-ray methods. The fluorescent behavior of L3-L5 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 L3 and L5 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.
New Fluorescent Chemosensors for Heavy Metal Ions Based on Functionalized Pendant Arm Derivatives of 7-Anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane / M. C. Aragoni; M. Arca; A. Bencini; A. J. Blake; C. Caltagirone; A. Danesi; F. A. Devillanova; A. Garau; T. Gelbrich; F. Isaia; V. Lippolis; M. B. Hursthouse; B. Valtancoli; C. Wilson. - In: INORGANIC CHEMISTRY. - ISSN 0020-1669. - STAMPA. - 46:(2007), pp. 8088-8097. [10.1021/ic700657j]
New Fluorescent Chemosensors for Heavy Metal Ions Based on Functionalized Pendant Arm Derivatives of 7-Anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane
BENCINI, ANDREA;VALTANCOLI, BARBARA;
2007
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 (L5) have been synthesized and characterized. Both derive from 7-anthracenylmethyl-1,4,10-trioxa-7,13-diazacyclopentadecane (L3) 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 L4, L5, and the unbranched L3 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 L3, [(H2L3)(HL3)](ClO4)3, and the complex [CdL3(NO3)2] have been determined by single-crystal X-ray methods. The fluorescent behavior of L3-L5 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 L3 and L5 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.File | Dimensione | Formato | |
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