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New fluorescent chemosensors for heavy metal ions based on functionalized pendant arm derivatives of 7-anthracenylmethyl-1,4,1 0-tri oxa-7,1 3-diazacyclopentadecane

Record type: Article

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 CuII, ZnII, CdII, HgII, and PbII has been studied as a function of pH in MeCN/H2O (1:1 v/v). The presence of CuII, HgII, or PbII 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 CdII at basic pH. The same effect is observed for L4 in the presence of CdII or ZnII at about pH 7.

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Citation

Aragoni, M.C., Arca, M., Bencini, A., Blake, A.J., Caltagirone, C., Danesi, A., Devillanova, F.A., Garau, A., Gelbrich, T., Isaia, F., Lippolis, V., Hursthouse, M.B., Valtancoli, B. and Wilson, C. (2007) New fluorescent chemosensors for heavy metal ions based on functionalized pendant arm derivatives of 7-anthracenylmethyl-1,4,1 0-tri oxa-7,1 3-diazacyclopentadecane Inorganic Chemistry, 46, (19), pp. 8088-8097. (doi:10.1021/ic700657j).

More information

Published date: 2007
Keywords: diaza-crown ethers, chemosensors, transition-metals, luminescent, complexes, sensors, aza-oxa, cation, anions, macrocyclic ligands, aqueous-solution

Identifiers

Local EPrints ID: 54231
URI: http://eprints.soton.ac.uk/id/eprint/54231
ISSN: 0020-1669
PURE UUID: fa070a9b-fcb1-467d-8cfc-8223cf5b5d52

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Date deposited: 31 Jul 2008
Last modified: 17 Jul 2017 14:36

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Contributors

Author: M.C. Aragoni
Author: M. Arca
Author: A. Bencini
Author: A.J. Blake
Author: C. Caltagirone
Author: A. Danesi
Author: F.A. Devillanova
Author: A. Garau
Author: T. Gelbrich
Author: F. Isaia
Author: V. Lippolis
Author: M.B. Hursthouse
Author: B. Valtancoli
Author: C. Wilson

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