The University of Southampton
University of Southampton Institutional Repository

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

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
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
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.
diaza-crown ethers, chemosensors, transition-metals, luminescent, complexes, sensors, aza-oxa, cation, anions, macrocyclic ligands, aqueous-solution
0020-1669
8088-8097
Aragoni, M.C.
aec09914-2339-4bd2-aa6f-3c80c0febe9a
Arca, M.
d852c450-c522-47cb-a577-9babf59dd503
Bencini, A.
4fe27f82-c77b-405a-b576-0edc4f1981af
Blake, A.J.
5bd685bc-00f0-4de6-b104-a50065ccb7f5
Caltagirone, C.
85626041-fdae-4dd6-8a5c-9a15194f8b63
Danesi, A.
55051bac-e7f0-4574-8a83-fff8f3848449
Devillanova, F.A.
20c07fe4-3b8e-46f4-a241-60ae5189efee
Garau, A.
5f40709b-2bc5-4d2d-9311-57813e34080d
Gelbrich, T.
42309d69-eaf1-4bb7-ba2e-db61f338e370
Isaia, F.
01929115-e3d5-4af1-b79b-439cfa32fd27
Lippolis, V.
6890f6ab-6860-4752-9639-5bdfeef0e90d
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Valtancoli, B.
61f6b77a-6483-4e73-8444-42453510883e
Wilson, C.
8f81973c-e436-4727-97fd-de70017a9f56
Aragoni, M.C.
aec09914-2339-4bd2-aa6f-3c80c0febe9a
Arca, M.
d852c450-c522-47cb-a577-9babf59dd503
Bencini, A.
4fe27f82-c77b-405a-b576-0edc4f1981af
Blake, A.J.
5bd685bc-00f0-4de6-b104-a50065ccb7f5
Caltagirone, C.
85626041-fdae-4dd6-8a5c-9a15194f8b63
Danesi, A.
55051bac-e7f0-4574-8a83-fff8f3848449
Devillanova, F.A.
20c07fe4-3b8e-46f4-a241-60ae5189efee
Garau, A.
5f40709b-2bc5-4d2d-9311-57813e34080d
Gelbrich, T.
42309d69-eaf1-4bb7-ba2e-db61f338e370
Isaia, F.
01929115-e3d5-4af1-b79b-439cfa32fd27
Lippolis, V.
6890f6ab-6860-4752-9639-5bdfeef0e90d
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Valtancoli, B.
61f6b77a-6483-4e73-8444-42453510883e
Wilson, C.
8f81973c-e436-4727-97fd-de70017a9f56

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), 8088-8097. (doi:10.1021/ic700657j).

Record type: Article

Abstract

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.

This record has no associated files available for download.

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

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 15 Mar 2024 10:45

Export record

Altmetrics

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

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×