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Sensors 2017, 17(8), 1816; doi:10.3390/s17081816

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

1
Department of Chemistry, Sungkyunkwan University, Suwon, Gyeonggi 16419, Korea
2
Graduate School of Nanoscience and Technology, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea
Present address: Department of Chemistry, KAIST and Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon 34141, Korea.
*
Author to whom correspondence should be addressed.
Received: 5 July 2017 / Revised: 3 August 2017 / Accepted: 3 August 2017 / Published: 7 August 2017
(This article belongs to the Special Issue Fluorescent Probes and Sensors)
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Abstract

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. View Full-Text
Keywords: spiropyran; metal ion; cyanide sensing; side-group effect; click reaction spiropyran; metal ion; cyanide sensing; side-group effect; click reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Lee, J.; Choi, E.J.; Kim, I.; Lee, M.; Satheeshkumar, C.; Song, C. Tuning Sensory Properties of Triazole-Conjugated Spiropyrans: Metal-Ion Selectivity and Paper-Based Colorimetric Detection of Cyanide. Sensors 2017, 17, 1816.

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