Highly selective thioalcohol modified phthalocyanine sensors for Ag(i) and Pd(ii) based on target induced J- and H-type aggregations: synthesis, electrochemistry and peripheral metal ion binding studies
We have described highly selective 1(4),8(11),15(18),22(25)-(1-hydroxyhexan-3-ylthio)-phthalocyanine sensors, M{Pc[α-SCH(C 3 H 7 )(C 2 H 5 OH)] 4 } (MPc(α-HHT) 4 , where M = Zn( ii ) ( 2 ), Cu( ii ) ( 3 ) or Co( ii ) ( 4 ) and HHT: -SCH(C 3 H 7 )(C 2 H 5 OH)). The formation of S-M-S {S = sulfur; M =...
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| Published in | Dalton transactions : an international journal of inorganic chemistry Vol. 41; no. 23; pp. 747 - 756 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
21.06.2012
|
| Subjects | |
| Online Access | Get full text |
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| Summary: | We have described highly selective 1(4),8(11),15(18),22(25)-(1-hydroxyhexan-3-ylthio)-phthalocyanine sensors, M{Pc[α-SCH(C
3
H
7
)(C
2
H
5
OH)]
4
} (MPc(α-HHT)
4
, where M = Zn(
ii
) (
2
), Cu(
ii
) (
3
) or Co(
ii
) (
4
) and HHT: -SCH(C
3
H
7
)(C
2
H
5
OH)). The formation of S-M-S {S = sulfur; M = Ag(
i
) or Pd(
ii
)} bonds on the periphery in the case of Ag(
i
) and Pd(
ii
) metal ions induces H- or J-aggregation, respectively, which results in significant changes in the absorption of the B- and, in particular, the Q-band. The binding ratios of Ag(
i
) to the periphery of
2
and
3
were found to be
ca.
2 : 1 and 3 : 2, respectively. On the other hand, the binding ratios of Pd(
ii
) to the periphery of the same compounds were found to be 3 : 1 and 4 : 1. The fluorescence of
2
exhibited distinct changes in response to treatment with Ag(
i
) and Pd(
ii
) ions in solution. The fluorescence spectra emission intensity of
2
was quenched upon titration with Ag(
i
) and Pd(
ii
) and a new emission maximum was observed upon titration with Pd(
ii
). FTIR,
1
H-NMR,
13
C-NMR, UV-vis, MALDI-TOF MS and elemental analysis data were used to characterize the novel compounds. Transmission electron microscopy (TEM) and field-emission scanning electron microscopy (FE-SEM) were also used as complementary techniques to investigate the morphology and to image the interfacial aggregates of
2
. The redox behaviours of the complexes were examined by voltammetry and
in situ
spectroelectrochemistry on Pt in a nonaqueous medium.
We have described highly selective 1(4),8(11),15(18),22(25)-(1-hydroxyhexan-3-ylthio)-phthalocyanine sensors, M{Pc[α-SCH(C
3
H
7
)(C
2
H
5
OH)]
4
}, MPc(α-HHT)
4
, {M = Zn(
ii
) (
2
), Cu(
ii
) (
3
) or Co(
ii
) (
4
)} (HHT: -SCH(C
3
H
7
)(C
2
H
5
OH). |
|---|---|
| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1 |
| ISSN: | 1477-9226 1477-9234 |
| DOI: | 10.1039/c2dt30244f |