Tuning Sensory Properties of Triazole-Conjugated Spiropyrans: Metal-Ion Selectivity and Paper-Based Colorimetric Detection of Cyanide

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Tuning the sensing properties of spiropyrans (SPs), which are one of the photochromic molecules useful for colorimetric sensing, is important for efficient analysis, but their synthetic modification is not always simple. Herein, we introduce an alkyne-functionalized SP, the modification of which would be easily achieved via Cu-catalyzed azide-alkyne cycloaddition ("click reaction"). The alkyne-SP was conjugated with a bis(triethylene glycol)-benzyl group (EG-BtSP) or a simple benzyl group (BtSP), forming a triazole linkage from the click reaction. The effects of auxiliary groups to SP were tested on metal-ion sensing and cyanide detection. We found that EG-BtSP was more Ca2+-sensitive than BtSP in acetonitrile, which were thoroughly examined by a continuous variation method (Job plot) and UV-VIS titrations, followed by non-linear regression analysis. Although both SPs showed similar, selective responses to cyanide in a water/acetonitrile co-solvent, only EG-BtSP showed a dramatic color change when fabricated on paper, highlighting the important contributions of the auxiliary groups.
Publisher
MDPI AG
Issue Date
2017-08
Language
English
Article Type
Article
Keywords

FLUORESCENT-PROBE; BINDING; MOIETY; ANION; CYCLOADDITION; TEMPERATURE; DERIVATIVES; DENDRIMERS; CHEMISTRY; CATIONS

Citation

SENSORS, v.17, no.8

ISSN
1424-8220
DOI
10.3390/s17081816
URI
http://hdl.handle.net/10203/226303
Appears in Collection
RIMS Journal Papers
Files in This Item
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